The Introverted Entrepreneur, Pt. III: Finding the Temperament to Toot Your Horn

In this final part of “The Introverted Entrepreneur,” we’re talking about singing your own praises. Did you miss part 1 (on networking as an introverted entrepreneur)? No problem, it’s right here. How about part 2 (on teamwork and collaboration)? Gotcha there too. Not sure what we’re doing? Start here.

It feels like tradition now, so let’s address a third myth that can often plague the introverted: temperament has no direct correlation to confidence. That is to say, just because someone is introverted or presents as reserved, doesn’t mean they’re not confident in their skills or abilities. An individual can appreciate their accomplishments, and yet find themselves struggling to articulate them adequately. This final edition of The Introverted Entrepreneur will address that quandary, while also sharing a few tips on how to manage it.

Penny (or Far More) For Your Thoughts?

I know the answer to “So, what do you do?” I know it. It’s not always easy to articulate, but I know the answer. The question, however, is “why is it so hard to articulate?” As it happens, there’s a physiological answer to this. I’ll try to explain simply:

There are two neurotransmitters that have been tied to temperament: dopamine and acetylcholine. Brains have both present, but they respond to each differently. Scientific studies have demonstrated that extroverted brains respond well to high levels of dopamine, while introverted brains tend to be more sensitive to it. These brains tend to respond better to acetylcholine, which runs along a longer neural pathway.

Why does that matter? Because it amounts to a thought literally taking longer to get from your brain to your lips. It’s not that I don’t know the answer to the question someone has posed, it just hasn’t arrived at its final destination yet. As a timely person in a family of “late-ies,” this frustrates me about myself at times. But it’s my reality, and I suspect it’s the reality of several others.

For entrepreneurs, this can be challenging because so much of business culture depends on being able to effortlessly talk a good game. Competence is often gauged on being able to make people feel good about what you have to offer, and we’ve culturally decided that elevator pitches, presentations, and a dazzling presence at networking events (see Part 1) is the best way to measure this. To be clear, I don’t say this to imply that introverts are inherently bad at these things. Rather, I want to draw attention to the idea that they relate to these scenarios differently. With that in mind, I want to share a few tips to make them easier.

Aim for Carnegie Hall- Practice, Practice, Practice

“I’m a higher education speaker and consultant, and I’m also a writer. I do both on a freelance basis.”

I don’t have an answer to how many tries it took me to boil down my answer to “So, what do you do?” to this. A bunch. But I had to practice saying it, until it came naturally. In some ways, the process mirrored my former life as a distance runner. I couldn’t get up and run nine miles from the start- I worked up to it from a huffy and stitch-inducing four blocks. In that transformation, I built an endurance that allowed that four blocks to eventually take less energy from me. For introverts, easing into these situations with practice isn’t unlike gearing up for a distance run. Both scenarios are ultimately geared toward making something potentially tiring, require less exertion.

Practice in the mirror. Practice with your pets. Have close friends, family, or mentors practice with you. Like memorized lines for an actor or memorized verses for a singer, eventually your answers, pitches, and cases made for your business will become second nature.

Show Your Work

I’m not always able to tell people what I’m “working on these days,” but I’m lucky to have a platform where I can show it. Jennifer Kahnweiler has cited social media as a strength of introverted leaders, and this is one of many ways in which it can be a source of power. I can stumble through trying to explain the outlets I write for, or I can direct them to a selected list of my published pieces.  I can share that I’ve committed to writing jokes on a semi-regular basis, or I can direct them to the #ammahaha hashtag. If actions speak louder than words, then why shouldn’t the results of my actions take center stage?

If you haven’t already found a way to show the impact of that thing you’re trying to build, know that it will speak for you in ways you might not be able to. Whether it takes the form of videos, publications, or customer testimonials, “showing your work” can help fill in some of the gaps that may widen if you leave a point out of a pitch or can’t quite find the words for something in the moment.

Schedule Your Bravery

While I didn’t create this tip – I have to give that credit to Paul Jarvis – I love it as a piece of advice for introverts. He writes:

I schedule sharing when I’ve got the energy and am feeling amped up to do it. That means putting newsletters in the cue [sic] sometimes weeks before they go out, pre-publishing blog posts to go live at later dates, and even scheduling tweets way ahead of time (I try to schedule the tweeting of articles I’ve written to go out at least once a day).

I like to do this when I first find out that something I wrote has gone live online, or when I’ve had a triumph in something I’ve worked on. Those scheduled shares, fueled by a natural energy burst, will then be parceled out over time, including times when I’m a little less energized. I can trust that people will hear about my availability for spring speaking dates on a regular basis, without feeling wracked by “they’re going to get sick of me” doubts with every press of “send.” That feeling of doubt isn’t exclusive to introverts, but it does tend to dampen their energy more than their extroverted counterparts.

Budding entrepreneurs who depend on awareness and exposure can employ this strategy to keep their name on the radar of interesting folks- but use it thoughtfully! Nobody likes a spammer/”robot”/carpetbomber. Keep it tasteful and moderate, but impactful.

Befriend a Megaphone

We’re often able to look at the accomplishments of others more objectively than we can our own; harness that power for yourself and someone whose work you believe in. As with part 1, I’d encourage those who have a hard time promoting themselves to find a willing hype-human to keep in their stable. It can be so much easier to promote the good work of friends, collaborators, or colleagues than it can be for ourselves. If that’s true of you, ask yourself: who can you create a mutually beneficial broadcast system with?

We’re often comfortable with people who can be vouched for, so it creates an additional level of trust for whatever you might be working on. And if you can do this for someone you’re hoping to work with more closely, it will likely endear them to you- when done in earnest. Keep that caveat in mind: we are operating in a world where BS detectors are (rightfully) turned all the way up. Avoid setting it off by engaging in these practices genuinely. Doing so falsely or with a solely self-serving goal will make you memorable for all the wrong reasons.

This guide is in so many ways a means of scratching the surface on this topic. What tips do you have that I should think about adding? What challenges might I have missed? Would love to hear from you!

Further Reading From Me:

The Introverted Entrepreneur, Pt. II: Temperament-Friendly Teamwork

In this second part of “The Introverted Entrepreneur,” we’re talking about embarking on the exercise of teambuilding and teamwork. Did you miss part 1 (on networking as an introverted entrepreneur)? No problem, it’s right here. Not sure what we’re doing? Start here.

As with this series’s first part, I feel compelled to start by dispelling a myth: introverts don’t hate people. An appreciation of solitude and occasional need for individual time has sown this nasty rumor, and I’m here to put it to rest.

Introverts (a) are capable of, and (b) truly enjoy, deep and purposeful relationships; this can be all the more true when these relationships are grounded in a common goal, interest, or objective. This means that once they find teammates and collaborators who they can work with well, they’ll be invaluable members of a team. We addressed a bit of the prospective synergy that introverts and extroverts can provide to one another in last week’s post; this week’s edition will allude to that as well.

How Do I Find These Folks?
In order to build substantive relationships that can not only fulfill you as a person, but also sustain the inception, growth, and development of a business, you have to find the people who would best fit your needs. This isn’t always the easiest, as we’ve already talked about. So I want to dedicate this portion of the post to other venues where these connections can be made.

First, my favorite, sending fan mail. I wrote with AND.CO earlier this year about the topic, and shared:

People love getting mail that isn’t bills, especially if those messages aren’t spam. After all, it’s always nice to know that your work is appreciated! So if you have a photographer that you follow on Instagram whose work always catches your eye, an artist whose work sparks something in you, or perhaps a blogger or columnist whose pieces resonate with you, send them a letter!

Now, it’s not a given that this piece of fan mail will yield an offer to work together. In fact, it’s pretty likely it won’t—but they do have the potential to start a relationship. Unlike the fan letters we used to send to heartthrobs as kids, these letters stand a stronger chance of standing out and making an impact. Relating on a professional and personal level could uncover commonalities that would be a natural fit for a joint project.

And ultimately, that’s the deeper purpose a collaboration is designed to fulfill. Whether the final product ends up being a podcast, joint article, shared promotion, co-taught class, or anything else you could choose to team up on, it’s about making the [entrepreneur] world feel a little less lonely. Even when we know the work we do is important, it can be hard to feel that way with little interaction or feedback. Consider collaboration as a way to keep your work fresh, original, challenging, and rewarding.

A preemptive note to this: fan mail should not be sent as flimsy pretext to ask for something. Trust me, the recipients can tell the difference. Genuine and earnest overtures of appreciation can get you somewhere; calculated openings for asks likely won’t.

Interested in the community of an online forum? Strategy or mastermind groups are possible and fruitful in spaces like Facebook, via Twitter using hashtags, and can even be conducted more intimately on platforms like Snapchat, MarcoPolo, Slack, or GroupMe. The key in these spaces is to watch (or “lurk”) as you enter, contribute knowledge where possible, and monitor the norms and expectations of a group space before making asks. Again, the asynchronous nature of those groups eases the burden of conversation, allowing introverts to take their time in contributing to a conversation or providing a response to a tough query. What’s more, an accessible archive (save Snapchat-based groups) means that you can come back to a topic or exchange later on- this isn’t always a comfortable thing to do in in-person conversations!

And finally, you can flex your connections with current friends and colleagues. While reaching out cold to folks might feel intimidating (a truth regardless of temperament, I want to make clear!), doing so with an assist from someone you already know can bear fruit in ways you might not have expected. For the last two years, I’ve hosted a blog series called The Defectors; as my existing connections run dry, I turned to previous contributors to help me find my next set of collaborators. These recommendations, coming from people who know me and who I trust, can strengthen “weak ties” (as in “I don’t know them, but I know of them”), remind me of strong ties I may have overlooked (“oh yeah, I could ask her!”), or create new links altogether (“this person sounds great, please connect us!”). This strategy, used on previous projects, led me to my current podcast hosts, a founding member of my current mastermind group, and several other frequent collaborators. Whose existing ties could lead you to the next great breakthrough for your business?

At the same time, it is essential to remember as an entrepreneur that your circle of friends and circle of professional connections don’t always intersect in a way that’s productive. What we’d hope would be a large intersecting area in a Venn diagram, might instead turn out to be only a sliver. That’s okay, often to be expected, and the best reason to employ several of these strategies together.

How Do We Create The Best Version of A Working Environment?
As someone deeply interested in temperament and how it affects how we work and live, adages about lapses in communication being the cause of conflict (“10% of conflict is due to difference of opinion, and 90% is due to tone of voice”) resonate as incredibly true to me. And in my work as a facilitator with teams and organizations centering around conflict, I see several versions of this in practice. When we parse it out as a group, I typically narrow it down to two dynamics: tending toward being quiet versus tending to talk things out; and preferring solitary work versus working in a communal/open environment. Recognizing, of course, that there is nuance in these classifications, it nonetheless works to help participants understand the differences that often accompany temperament.

The exercise encourages participants to share their first assumptions about why their “opposites” behave as they do, and then the true motivations behind those actions are shared. The result? The next time someone doesn’t contribute as expected in a meeting, or opts to work with their door closed, someone who works differently has the context to push past their assumptions- recalling and therefore revealing the actual motivation for that action. “Francisca wasn’t not listening, she just needs a bit more time to think about what we posed in the meeting.” or “Jarvis isn’t mad that it’s so loud in here, he just needs the quiet to access his thoughts.”

I say all this to encourage you, as a business owner and in turn as a custodian of a budding working environment, to prioritize understanding the work style and work preferences of those who you work with. How flexible are you willing and able to be? What are your organizational expectations and, for that matter, dealbreakers? And in the work environment that you’re building, do people have the opportunity to know one another well enough to distinguish temperamental differences from quirks at best (and character flaws at worst)?

What Happens When Conflict Arises?
As I alluded to above, a better understanding of what communication styles might represent is essential when trying to mediate and resolve conflict. In fact, I recommend setting ground rules during “peacetime” for how conflict will be handled. These ground rules can be based in individual challenges, and serve as an aspirational way to improve our typical communication patterns.

For example, while I am incredibly slow to anger, I will sit on small annoyances…only to see them explode on my friends, coworkers, or loved ones after they accumulate. So a ground rule I would set for myself would be to tell a person when something is bothering me, in a timely fashion (24 hours or fewer). Someone who seeks to deflect blame toward others might set a goal of taking three breaths and examining the multiple sides in a conflict; an individual who struggles to engage in conflict at all might aim to reflect on feelings before sharing them with others. In all these cases, creating a strategy that allows improvement upon our occasionally unproductive instincts, can change the way we engage in these issues.

What about confronting the conflict itself? A good rule, irrespective of temperament, is to face as much of the situation face to face as possible, but allow any time that is needed to de-escalate or reflect on the issue at hand. This dual-pronged strategy prevents some of the ambiguity of tone that can come from asynchronous communication, but also allows each party the time and space to choose their words intentionally. It also addresses each “type”‘s challenges with care. While introverts can sometimes struggle to articulate their challenges in real time (especially during points of high stimulation), having the grace of “let me think about how to say that” can yield a more cogent argument when it comes to them. Similarly, while slowing down might be difficult for individuals who talk and think nearly simultaneously, the challenge to slow down and choose words more intentionally might prevent some of the hurt that can come from speaking extemporaneously.

Recognizing that the nature of entrepreneurial culture means that the people with whom you’re in conflict are likely both your colleagues and your friends, it can seem dismissive or trite to encourage a separation between personal issues and professional ones. But I promise you, it’s possible. Ad hominem (“to the man” in Latin) attacks, or ones directed toward a person rather than the issue or challenge at hand, can destroy key relationships. This means preparing to tackle a situation with an understanding of what’s really upsetting you or causing a problem. To be clear: this is not always easy to do. Drilling down into the issue with a “five whys” approach (starting with what you see as challenging, asking “why,” and being honest; after five “whys” the problem often looks very different) may help you gain some clarity on the root issue, and not just the symptoms that may finally be starting to flare up. Once you’re at the root cause, any healing remedies you elect to put in place – together – will have a better and more lasting chance of yielding a cure.

This guide is in so many ways a means of scratching the surface on this topic. What tips do you have that I should think about adding? What challenges might I have missed? Would love to hear from you!

Further Reading From Me:



The Introverted Entrepreneur, Pt. I: Working the Room, Your Way

In this first part of “The Introverted Entrepreneur,” we’re talking about the frequently discussed challenge of networking. Not sure what we’re doing? Start here.

Let me get this off my chest first so we can dispose of the myth: discomfort with networking is not a purely introverted trait. Frankly, most people hate it. And I get that. The idea of making conversation toward either a specific professional goal, or as a means to be “memorable,” is an arduous task for most people.

However, the need to network efficiently and effectively is especially crucial for entrepreneurs. Building a business can be isolating, and getting to know others who have embarked or are embarking on the journey can be comforting. And from a more utilitarian perspective, it is these connections that eventually lead us to our occasional collaborators, co-conspirators, or co-founders. So yes, while there is some dread associated with leaving our physical cocoons (home or the office) as well as our mental and emotional cocoons (“do I have to go?”), there is undeniable value in making the brief journey out of that space.

That “do I have to go?” dread is real. And as I’ve shared previously in a move of accountability to stop me from whining about this, “catering to my own comfort isn’t conducive to building strong relationships, social or professional. This is an instinct that I need to fight, and am actively working to combat.”

So, how can you make these events work for you when you’re in need of the connections that your personal energy stores may not always welcome?

Go in with a plan. I tell people I’m coaching or working with often: it is often neither productive nor feasible to leave rooms like these with everyone present knowing your name. What’s more, as energy stores flag, you might find that those you met at the beginning and those you met at the end may see different versions of you. I’ll elaborate, using a snippet from my 2014 book The I’s Have It:

A hangover from alcohol or sugar (and yes, a sugar hangover is real) comes from the consumption of an excess amount of something that, in appropriate amounts, has few ill effects. But after we reach a threshold that our body can handle, we start to feel ill. The introvert hangover is our body’s response to excess- irritability, short temperedness, and a loss of focus. When we look back on some of the negative characteristics associated with introversion- assumptions of judgment, self-centeredness, and aloofness – one starts to wonder if these conclusions were drawn from introverts who were, as [my friend] Chris says, hungover. These characteristics generally aren’t true from a “fully charged” introvert, but could certainly be mistakenly assumed of an introvert in dire need of a recharge.

I remember very vividly hitting this point during an information fair for my graduate program; my first interview with a prospective assistantship supervisor was upbeat, well-informed, and conversational. My seventh? Well, it was…not. Nearly ten years after the fact, I remember sinking heavily into the chair, the words “I’m so sorry, I’m so tired” tumbling out before my brain had the time to stop me. I did not get that job.

If I were pitching support for my business to that last assistantship supervisor, there’s no way I would have gotten their support. And indeed, for entrepreneurs these interactions carry an additional burden. How do you put your best foot forward when not just you, but the merit of the idea you’re seeking to build, is being judged by the quality of these interactions?  With a plan. With notes. With a “cheat sheet” of your own design.

If you’re able to access an attendee list beforehand, take note of who you might be sharing the space with that evening. If you’re unable, perhaps take an initial pass through the room in search of familiar faces. The goal with either maneuver is to identify where your energy burn will yield the strongest outcome. This is an essential bargaining move when the time and energy you have to be the best version of yourself, is being depleted over the course of an evening or an outing.

I often use a cell phone battery to help articulate this idea; if your phone’s at 40%, that’s not the best time to think about streaming a movie or documenting something via Snap story. But reading an article, or maybe a 22 minute TV episode? That creates less of an energy burden, and doesn’t push you to your “red zone” as quickly. Plans, goals, and a deliberate plan of attack slow your time to your red zone. Use them liberally to make the most of these opportunities.

Take the assist where needed. We all need a “wing-human” to help us be our best in moments that challenge us. Whether those moments take place in sticky-floored bars on ladies’ night, or in the Atlanta Marriott’s harshly lit Salon D, going in with a partner can help make a difference in how we approach these potentially draining scenarios.

Picking a wingman as an entrepreneur carries an additional wrinkle; select someone who knows you well, but also knows your enterprise well. If you, for any reason, leave something out in conversation, who in your “squad” can jump in with the assist to make you look good? Who will speak well of what you do on your behalf? Who can answer that “so what do you do?” question for you the tenth time, because the first nine have just taken it out of you?

To that end, there’s a version of the assist that isn’t a person, but rather an action: how can you schedule your day in a way that helps you come to these events – to extend the cell phone metaphor – at 100%? For an example, if I’m headed to a conference where I’ll be expected to be present at a booth for two hours and chat with attendees, I’ll make sure the preceding hour or two is mine alone. That “assist” is akin to plugging myself in on a charger, switching myself to “airplane mode,” and powering up before high demand on my energy stores.

Whether the assist comes from someone else, or from you, the goal is the same: to give you what you need to present yourself well. Which reminds me…there is what I call “a kill-switch” moment, where you know you’re spent and that any further stimulation would lead to diminishing returns. You know when it’s arrived, you feel it. Strongly. Take that cue when it comes, and help your wing-humans recognize it in you. Whether you need to excuse yourself politely, or someone in the inner circle needs to identify a “signal” and step in, know that honoring this need isn’t quirky, selfish, or shameful. Rather, it is your body’s way of signaling you that it has had enough, and that with some rest you’ll be at your best again soon.

Let social media “hold you to it.” Even with the best of intentions, I don’t always hold myself accountable as I should to productivity at networking events. This can occasionally surprise people who have interacted with me via social media, and find me to be self-assured in those shared moments. And indeed, Jennifer Kahnweiler has recognized that a considerable strength of introverted leaders lies in their use of social media. The option to communicate asynchronously, with multiple media (I’m partial to GIFs myself), and the time to contemplate responses where needed, make a difference in how introverts can present themselves congruently.

Connecting this point to the earlier one of making a plan, I like to put out a call via Twitter or LinkedIn ahead of events I’m apprehensive about. It helps me see who in my networks I might see in that initial pass of the room, or who these people might know in those rooms. Even a quick “hope to see you there!” holds me accountable to stopping that vaguely familiar face and saying hi, or enlisting that friend who’s also going as my wing-human for a “scarier” encounter, like approaching a panelist or a prospective investor or collaborator.

And if I hit my kill-switch beforehand, or for some other reason don’t get around to flexing that connection? Sending another note with an apology and hopes of connecting again soon can help. Some people who I connect with regularly are ones who I reached out online, missed them (or froze in the moment, that happens too!) but stayed in touch and eventually did meet up with. If these are folks you’re hoping to work with or be supported by, these follow-up moments are crucial because they demonstrate commitment and accountability, even when the goal wasn’t met.

I hope this helps you tackle some of your fears, anxieties, and energy drains around the next big “room” you get to sell yourself in. Stay tuned- next week we’ll be talking about how to connect with prospective collaborators, and how introverts can effectively make meaningful overtures toward these goals.

This guide is in so many ways a means of scratching the surface on this topic. What tips do you have that I should think about adding? What challenges might I have missed? Would love to hear from you!

Further Reading from Me:


Coming Soon: The Introverted Entrepreneur

A few weeks back, I received a message from someone who had heard my appearance on Hubspot’s The Growth Show podcast. He posed a question that got me thinking…hard.

I’m an introvert myself and someone who really enjoys mentoring and advising tech startup founders. The usual guidance about building startups is all about moving quickly (out of the world of ideas into execution!), getting out and talking to potential customers and building your network (often through meetups etc). All things that I think are especially tough or mentally draining for introverts.
This leads me to ask if you’ve written about, or have any guiding tips, for introverted founders to work through these in building their business? (emphasis added)

I have to be honest, I could have sworn I had covered this at some point.

Turns out, I haven’t. But it’s absolutely true. There are certain machinations that are part of the startup or entrepreneur experience, that drain introverts a bit more than they might extroverts. I haven’t yet talked about the nature of temperament as it pertains to this experience. But I want to. 

I want to round out my year on the blog with an examination of three parts of the founder/entrepreneur experience where temperament often comes into play: networking and connection building, collaboration, and self-promotion. I’ll seek to share examples from my own experience, as well as those from other people whose work I have grown to appreciate. Through it all, I hope you’ll see that success in a founder or creator role can look different from what you might have thought.

Stay tuned in the weeks ahead for my take on the topic, and thanks to Peter Moore of Starteer for the inspiration!

The Defectors, Series 2: A Different Look at “Defection”

(I’ve said much of what I want to say about the conclusion of this series in last year’s closings, which you can find here and here. But there’s a bit more…so read on!)

“Why the word ‘Defector?'”

About a week into this edition of The Defectors, I got this question from my agent Ken, who I appreciate for challenging me to think about what I think and say in new ways. In truth, I liked the confident charge the term implied. Defecting is a decision, a clear choice that someone makes to depart from what they’ve been doing or where they’ve been going. People defect from political parties, from countries of citizenship, from organizations that they call home.

But what Ken urged me to think about, is that defection often happens violently. It frequently comes into play where people are given no other choice but to leave.  It’s seen as less of a confident walk away, and more of a fraught tearing of bonds. Even after looking at it that way…I like that it’s provocative. What’s more, even though it’s provocative, I stand by my decision to use that exact word.

Why? Because I see so much of that assumption grafted upon those who choose to follow the defector path. There are a lot of hurt feelings, confusion, cries to stay, and even after the departure, tinges of disapproval from those who stayed on the well-worn path. There is a difference between the earnest “how are things?” and the one soaked in “do you regret it yet?” Yes, we can hear the difference- and for my part, even when it’s hard – especially when it’s hard – I don’t regret it for a second.

I was reminded of a post I wrote on this topic a few years back, well before my own defection and before I started talking to others pointedly about their own, called “Pull, Don’t Push.” An excerpt:

One of the elements of our profession that I struggle with most is our propensity to shame or look down upon those who elect to leave the field in favor of other pursuits. Being a field of personable people, we take offense at this decision, concerned that its our fault or that we have some duty to keep them “within our ranks.” But, as Chris Conzen illuminated in one of my favorite posts of his, this may have nothing to do with us. We’re typically offended, concerned, or hurt by what we’re seeing as a push. I want us, as a profession, to look at this another way.

The post used the “second act” comedy careers of Ken Jeong (former doctor), Retta (former chemist) and Bill Cosby (former teacher, and pre-scandal of course) to illuminate the idea of being pulled toward a new pursuit or way of working, rather than away from an existing one. I highlighted the element of choice here, acknowledging that this manner of making change is different from those who feel forced out (which, to make abundantly clear- the circumstances around that form of departure also need to change):

There are those who leave the field because the pressures of their role have caused them to seek other options, or because their belief in the field is inconsistent with their reality. I completely understand that this can happen. However, this post is not for or about those people.

I like the choice of “defection” as a means to describe this new world of work that many have chosen to enter, because so many look at it in that traditional way at first glance. The definition of “defect” as a verb is “to abandon a country or cause in favor of an opposing one” (emphasis added). It is my sincere and fervent hope that you’ve learned, over the course of this month – and through season one – that these causes are not in opposition with one another.

So how can we remove the oppositional orientation of these non-campus based roles, and make professionals more aware of their myriad options?

  • For those who “tap” undergraduate students with potential to excel in this field: Speak not just of the on-campus opportunities to affect student development and well-being, but also of the off campus opportunities. How could professional associations be better for their contributions? Auxiliary service providers? Honor societies?
  • For those who advise students through supervision or faculty roles: Speak about these additional opportunities not as secondary or fallback options, but as legitimate parts of a fulfilling path for one’s career. In what ways has your work been impacted by the professionals serving the field in other ways? How have you collaborated with them, and how have they supported your work?
  • For graduate students evaluating their entry into the field: don’t sell non-campus-based positions short. They are not a substandard or “backup” form of engagement in higher education; they’re simply different. No better, no worse…only different. Do any of these different options look enticing? Use your status as a student to your advantage; ask questions, conduct informational interviews, meaningfully incorporate these options into your search if they pique your interest.
  • For professionals looking critically at their next steps: Get creative with how your skills, abilities, and perspective can impact the world of work. Who can benefit from the areas in which you shine? In what other areas of the field could you shine? Several of the Defectors in this year’s series have volunteered their contact information, who might be able to share their story and inform your next steps?
  • And for professionals who are friends, colleagues, or supporters of Defectors: it is, more often than not, not personal. Behave accordingly. Support these folx through their transition into a new form of work. They’re enduring a good bit of change, but it’s likely that the change is borne of a pull toward a new life. Encourage it.

I am immeasurably appreciative of the individuals who chose to share their stories through this series, and to the team at Presence for helping me create a series that could compensate these individuals for their work. If you’re looking for a taste of the Defector lifestyle, I urge you to get in touch with Presence– they are a tremendously supportive organization that has created a wonderful home for several former student affairs practitioners and student leaders, all in service of making the lives of campus-based professionals easier. Let’s please keep this conversation going year-round; it matters too much to leave to one month a year!

If you have defected, and are interested in participating in future iterations of this project (another blog series? A podcast? An limited-run series of on-camera interviews?) please let me know so I can reach out when the time comes!

The Defectors, Series 2: Kayley Robsham, Presence


Today’s Defectors contributor post, the last of series 2, comes from Presence’s Kayley Robsham. Not sure what we’re doing here yet? All is revealed here.

It’s been two years since I wrote my first post about defecting.

I learned so much from falling out of love with a career path in residence life I thought I wanted, I feel compelled to share my story about what I’ve learned.

To begin, this journey was very much unplanned. You don’t expect to fall out of love with a career—much like entering into serious partnership or marriage, I imagine. When I made the decision to accept the position with Check I’m Here (now Presence), I never thought this was where I was going to be.

As I shared two years ago, the doubts I identified were considerable, enough to make me want to test new waters:

I had seen women in leadership roles that seemed like they couldn’t move up the student affairs ladder (never mind queer women). How long would it take me to “climb the ladder” and prove I was worth it? Why did I feel like I had to? Things like work/life balance and lack of women in leadership positions in a field heavily populated by women made me think advancing was impossible (in addition to moving across the country if I wanted to take higher level positions in the future). Considering the quality of life and systematic deterrents I decided to consider entrepreneurship in higher education instead.

I was proud of myself for trusting my gut instinct and I was pretty damn excited. I stepped out of the light of I what I should be doing, and started to look forward to a space where I would feel more authentic and dedicated. Up until that point, I had worked myself to the bone and had not prioritized self-care. I was depressed and was hard on myself for oversleeping, drinking, eating unhealthy, and the list goes on. My new job made me see self-care in a different light, and that’s when it settled in that I made the right decision.

I think many people in the early stages of their working life feel this pressure that they have to figure out everything around their career at a young age. My observation is that most people go through many career changes and don’t find their calling until later in life.

Elle Luna’s book The Crossroads of Should and Must: Find and Follow Your Passion validated my own feelings of not being sure of what I want to do. She embraces the message and highlights differences of being in a job, creating a career, or finding your calling. Luna explains there is a difference between going to work and becoming one with your work, which I believe takes patience and time to figure out.

Although I do feel much better about how I am spending my time and living my life, I don’t think I’ve found my calling just yet. There is so much to do and to explore, and I’m so excited to see where my strengths lead me and what new strengths I potentially develop.

Here is what I’ve learned overall: If you are in a job that is not making you happy, and you know there is another job, career, or calling you’d rather be doing, no matter what it is, it is up to you to facilitate change. For me, I didn’t want the ‘what if?’ to be in the back of my head forever.

Now, I feel like I’ve had the time to create more opportunities for myself since I’ve defected. I’ve taken the time to get to know who I am, and I’m still figuring out where I’m headed. Two years ago, I noted, “Pushing myself to apply to a position that aligned with my professional goals outside of my comfort zone has strengthened my inner voice immensely.” That notion remains true, and I encourage you to similarly empower your inner voice: who knows where it could take you?

It was a hard decision for me to defect, but I knew I wanted to be happy in my job, whether I was working in student affairs or adjacent to it.

Kayley Robsham (she/her/hers) is a life coach, inclusive data advocate, and teacher of social media marketing to fellow solopreneurs in St. Petersburg, Florida. In 2015, she found herself as a new student affairs professional and decided to make the jump to educational technology (“edtech”) to impact the lives of thousands of SA pros and students. She’s currently the Community Engagement Manager at Presence.

The Defectors (series 2) is sponsored by Presence. At Presence, we’re working to solve all of the higher ed problems you’ve always heard couldn’t be fixed. If you love asking questions, finding solutions to intricate problems, and learning about new people and places, we want you to join our team. Check out our open positions and apply today!


The Defectors, Series 2: Corey Bates, Tribridge


Today’s Defectors contributor post comes from Corey Bates, Campus Recruiter at Tribridge. Not sure what we’re doing here yet? All is revealed here.

Tuesday, June 21, 2016…that day is one which will always stick out in my mind. It was my last day that I chose to be a student affairs professional. For six years of my life (at that point), I dedicated my time professionally to becoming a dynamic leader in this space. To think, I spent ten years on some form of a college campus learning, growing and being challenged for the better. However, I knew that on this day, I was ready to use the same advice that I would share with students for years; it was time to move forward and apply all of the learning I attained within the four walls of the college environment and apply it to the real world.

Getting to a place of self-assurance with this change did not come easy. At the start of the Fall 2015 semester, I was lost. I somehow went through the motions of all the responsibilities that I needed to complete. It brought about a significant period where was depressed. Externally, people would have never known (what smiles can hide), but I knew what was going on internally. I was not happy, knowing that there was a moral, value and purpose based disconnect to the work that I was responsible to complete. However, I knew that something needed to change.  

Moving forward into the Spring 2016 semester, various ups and downs took place in my life, and I felt like I could not grasp for air. However, the moment that I decided to choose me and my happiness was the moment where light started to illuminate the dark hole. I submitted my resignation from the role I had at the time and started job searching in the midst of wrapping up another semester. It took a while to figure out my new professional game plan. At that time, I thought I would be an influential figure in higher education nationally as my career grew. Thus, I took time to think about what made me happy professionally.

I recognized quickly that I thoroughly enjoyed work I did in training and development for students and professional staff. With all of the positions that I had throughout the years, I was tied that work in some way. Sometimes, I wished I was able to do more of it, but other responsibilities took precedent. Coming to that realization helped me to strategize how I would market those skills as I apply to corporate training and development jobs.

Once I left my time working in higher education, I went into full job search mode. I spent six weeks dedicated to the search, essentially applying to jobs like a 9 to 5 job every day. It was in August 2016, however, where breakthrough started to come, picking up two jobs. I was thankful that I somewhere to go and something to do at that point. Though these jobs were two temporary positions, they gave me industry experience that I was lacking. Many companies that I would apply to denied me because of this one component. It also allowed for me to build a new network of professionals in the HR space, particularly in Talent Development. While working these two temp jobs, I still job searched every free moment that I had to spare as I put forth great effort in the work that I was doing at that time.

Three days before Thanksgiving 2016, I landed my current role, eventually starting in January of this year. I could not have been more thankful. I work as a campus recruiter for Tribridge. The company, in a nutshell, solves problems with technology, utilizing software solutions to ensure companies are able to do their work efficiently. I go to various campuses within the state of Florida to find top talent to work for our company. The position has given me opportunities to coach job seekers with resume writing, networking and interviewing skills. Also, as my role was hybridized within two months of starting, I complete various projects that are focused on talent development, which was my initial job seeking goal when this journey began. The company has given me the platform to learn and apply all that I can to be an effective Talent Development professional.

Besides experiencing in corporate that bonuses do exist, lay-offs do happen and telecommuting to work is the best concept ever, I have learned that transferrable skills have significant weight when leveraged correctly in the job search. If it was not for my experiences in training, development, recruitment and event planning within higher education, my job search could have went much longer. Another lesson that I took in during this time is taking more care of me in ALL areas of my life. Physically, spiritually and emotionally, I was fulfilled. However professionally, I was neglecting those thorns on my side that started to affect various areas of my life. It was great to come full circle in that area and be ok with finding that place of fulfillment.

In the end, the experience taught me what it meant to simply “couch in the uncomfortable”. It is the space where you learn a great deal about your capabilities and strengths when plans seemed to be flipped upside down. Working in this new space has propelled a significant amount growth which has given me the confidence to truly live fearlessly.

The Defectors (series 2) is sponsored by Presence. At Presence, we’re working to solve all of the higher ed problems you’ve always heard couldn’t be fixed. If you love asking questions, finding solutions to intricate problems, and learning about new people and places, we want you to join our team. Check out our open positions and apply today!


The Defectors, Series 2: Brian LeDuc, Education Design Lab

Today’s Defectors contributor post comes from Brian LeDuc, Education Designer at the Education Design Lab. Not sure what we’re doing here yet? All is revealed here.

Education Designer. Campus Director. Higher Education Consultant, Performance Technologies. Manager for Leadership Programs. Graduate Hall Director. This is what I’ve been up to for the last seven years– for the most part, not your “traditional” set of job titles for a guy with a Master’s in Educational Administration. What I’ve found no matter where I’ve worked, is about stories, signals, and skills. Entering a new industry or role is partly about explaining your story, or foundation and interest in a new role, partly about translating your skills and abilities (and the gaps), and partly about putting in the time and effort to learn how to close that distance through signals of your investment of time, energy, and learning.

When I graduated from A&M, I was compelled by an opportunity to work not only in leadership education, but focused on systemic social issues, and in partnership with a dozen other Universities. It was the combination of student contact and engagement beyond the walls of campus that drew me in.  But it wasn’t long before I felt the limitations of working at an institution of 27,000 students but only impacting only a few hundred.  I felt like the information and insight I gained through my experience at NACA meant I had a responsibility to begin to take action beyond plugging into (what felt like) the “status quo.”  So I looked to my SAAHE network, exploring what other paths my work might take, and understanding the various roles that might allow me to view the field from a new perspective.

One of the things I overlooked at the time was that many of the graduates of the program weren’t working on a college campus at all. They were working at foundations and technology companies, non-profits and consulting firms. They were working in the ecosystem of higher education, but not directly with students.

Further, what I didn’t realize was that the conversations that were most interesting to me would actually be about the trends in higher ed at the intersection of student development, student success relevance of higher education, preparedness for life after college, and building a sustainable future for the association and higher education as a whole.

I wanted to impact more than just the students who I was able to connect with one on one, recognizing that even at my best, the systems I was working in weren’t prepared for the changes ahead in higher education.  

And while I was concerned that I wouldn’t be working with students everyday, I was excited by the idea of supporting thousands of campuses across the US at a place I saw making a difference. Watching the growing role that technology was playing in higher ed, and the focus and attention on advising and student success, I leapt to where I thought the puck might be headed, joining the EAB after a core of early Universities started implementing their advising technology. And that itch about losing connection with students altogether didn’t go away.  

Thankfully, the Kiwanis Key Leader program welcomed me on as a Lead Facilitator to their program, so 3-4 weekends a year I hang out with 60 high school students and chat with them about servant leadership, community engagement, and the leadership skills that are critical for success. And my time at EAB was pretty awesome. And in the process, I learned about project management, client relationship management, data analysis, improved my presentation skills, and learned about content management and cohort services (by building a few case studies), and used my background as a higher ed administrator and time on campus to inform our strategy for change management on campus while being immersed in work at a tech company building a new product. Oh, and I learned a bit about improv from The Second City along the way also.

Through EAB’s dual role in technology and research, I kept a pulse on the industry trends as a whole, and started to see several college alternatives and code schools focused on building specific skill sets emerge. I next joined The Iron Yard (a 12-week, intensive, coding bootcamp  startup for career changers looking to become software engineers) to see what life was like on the inside, alongside all of the excitement, speed, uncertainty, and frustration that comes with startup life. I fused my work as a higher ed administrator combined with an understanding of the tech world and married them with leadership education and skill development.

Serving in a role that placed me at the center of admissions, enrollment, student support, and career preparation and placement drastically changed my view about what college could look like, and the truths that we hold about what education is today.  While it wasn’t perfect, the deliberate focus on developing practical skills with career outcomes in mind and oversight across the entire student lifecycle and experience made me confident that traditional universities could benefit from exploring new approaches and models for their work.

Now armed with that knowledge and perspective, I’ve committed to combining the insight from bootcamps, startups, and tech companies in my work at the Education Design Lab, where we partner with education institutions using design thinking and other tools to consider how they might design education toward the future of work. Bringing in the threads of human-centered design used in tech, and skills like qualitative research, counseling, relationship and project management, and facilitation, I’m deepening my engagement of design thinking to build new models and pathways for education…that apply what I learned at The Iron Yard into traditional higher education, and new contexts.

I’ve shared quite a bit about how I feel about Education Administrators and their role in the future, and the ways that it’s likely to change.

Higher Education is experiencing massive disruptions; technologies that enable new approaches to engaging students and enhancing their learning, emerging educational pathways that didn’t exist before, and the constant evolution of the world of work and the knowledge, skills, and abilities that employers expect from new graduates. The emerging trends of “traditional” students is non-traditional: an older, part-time, student of color.

I see my work always landing somewhere between education, technology, education, and workforce informed from experiences across each of those areas– and it will be the result of exploring new opportunities to use and develop skills and knowledge that can translate across industries and organizational contexts. It will be the result of continuing to keep a pulse on trends in higher education, and thinking critically about “where the puck is going” and how to stay prepared and relevant to contribute in new, meaningful, ways.

I want to help to shape higher education to adapt to the changing worlds of work, technology, and culture, which means being close enough to help, but far enough not to be distracted by “business as usual” besides the frame to consider adapting from.

Brian serves as an Education Designer at the Education Design Lab. Since earning his Master’s degree in Education administration, Brian’s been serving across higher education as a leadership educator, helping universities improve retention and graduation rates using technology, and running a coding bootcamp in DC.  Brian likes running other things too, like Meetups and marathons. When he’s not on the Potomac in a kayak, camping in the woods, or in the audience at a concert, he’s probably watching The Office or Arrested Development on Netflix. Give him a shout at

The Defectors (series 2) is sponsored by Presence. At Presence, we’re working to solve all of the higher ed problems you’ve always heard couldn’t be fixed. If you love asking questions, finding solutions to intricate problems, and learning about new people and places, we want you to join our team. Check out our open positions and apply today!


The Defectors, Series 2: Paul Brown, Roompact

Today’s Defectors contributor post comes from Paul Brown, Director of Curriculum, Training, and Research at Roompact. Not sure what we’re doing here yet? All is revealed here.


Those that know me, know that I’ve always tended to follow my own lead. My career path— especially recently— has been no different. When I graduated with my undergraduate degree from SUNY Geneseo, I took a safe route. Not quite ready to enter the “world of work,” I went straight on to get my Master’s Degree in College Student Personnel from Western Illinois University. In saying it was a “safe route,” that is not to say I wasn’t interested and passionate about the field—it was quite the opposite—but staying within the known world of academia was relatively easy.

After Western, I worked at Miami University and American University in residence life and academic affairs roles. That finally brought me to Boston College where I was a full-time PhD student in Higher Education. My initial goal in seeking a PhD was to become a faculty member. I loved teaching. I loved research. It was a good fit. As I progressed through my PhD, however, a side gig developed. I began going to colleges, universities, and conferences to speak about my research into the influence of digital and social technology on the college student experience. I began traveling more as a result of it and became hooked. I also started blogging and participating in knowledge communities online.

Having this kind of academic and creative freedom felt amazing. There was almost a point where I considered pursuing it full time. The realities of working for yourself, however, including funding your own health care, paycheck instability, and an itinerant lifestyle- which wasn’t for me. I wanted something “in between.” I wanted something with the stability of having an employer, but with the creativity of being your own employer.

I was open to making a career switch, and since I studied technology’s impact on college students, this opened up the opportunity for me to work for higher education-related technology companies. Out of sheer luck, I found Roompact, my current employer. Roompact makes residential education and curriculum software for college and university housing departments. It has been a perfect fit—combining my residence life and higher education background with my passion for and research on technology.

My current job has the creativity and flexibility that I craved. Working for a relatively young company means we are often figuring out new processes and solving new problems that none of us have ever encountered before. There’s no one to ask about how to do something. You rely on each other, use your network, and be willing to try, fail, and learn. This happens nearly every day.

Working at Roompact has also given me personal flexibility. Flexible vacation means I can continue to do speaking engagements on the side. Having a role that is more project based means I can break out of the traditional 9-5 weekly schedule. And finally, being able to work electronically means that I can do my work from almost anywhere in the world.

The transition was (and is) not without its challenges. It has challenged me to re-think and examine my identity which had been wrapped up in colleges and universities for so long. This hasn’t necessarily been a bad thing, just different. It has also challenged me to maintain and grow my network with friends and colleagues to stay in “the conversation” within the field. I remain passionate about the work we do to help students.

Making a jump to a higher education adjacent field has been an amazing experience for me and one that I don’t see ending anytime in the near future. The truth is, work should be something you’re passionate about and that challenges you. My current job has that and it doesn’t seem likely to stop anytime in the near future.

A career is a journey and not a destination. Right now, I’m very happy with where that journey is taking me. As I evolve, so does my career.

Paul Gordon Brown is currently the Director of Curriculum, Training, and Research at the residential life and education software company, Roompact. While he was a PhD student in Higher Education at Boston College, Paul started a successful speaking and consulting business coaching colleges and university on the impact of social media and technology on college student learning and development. For fun, Paul travels the world and delights in finding weird and offbeat roadside attractions. Reach out to him at, or via Twitter @paulgordonbrown.

The Defectors (series 2) is sponsored by Presence. At Presence, we’re working to solve all of the higher ed problems you’ve always heard couldn’t be fixed. If you love asking questions, finding solutions to intricate problems, and learning about new people and places, we want you to join our team. Check out our open positions and apply today!


The Defectors, Series 2: Tara Singer, Omicron Delta Kappa


Today’s Defectors contributor post is a cartoon (the first for this series) created by Tara Singer of Omicron Delta Kappa . Not sure what we’re doing here yet? All is revealed here.

When I was a university administrator, I would throw a Happy Fiscal New Year’s party for my staff.  As of July 1 each year, we felt rich because the budget distributions had been made, and we could go shopping for those types of office supplies and equipment that we had put off purchasing until there was money available again.  We could update and print revised versions of publications.  In some years, we could even book travel.  The money from tuition and state funding allowed us to begin the academic year with the hopes that we would have enough funds to get us through to the following summer.  

As a non-profit administrator, I don’t have access to resources that “miraculously” appear on July 1st.  Whatever money that our nonprofit has in the checking account from the previous fiscal year is carried over, but there won’t be new funds until we (a) secure new members and (b) raise more money from donors.  Both of those activities don’t begin in earnest until about the first of September making the summer months budgetarily lean.  I’m sure my colleagues who have gone into business for themselves experience a similar, if not more significant, challenge.  It may be the price to pay for not having a budget based on the whims of a state legislature, but it is definitely worth it.

Tara Singer is the executive director of Omicron Delta Kappa, the National Leadership Honor Society.  Prior to working at O∆K, she spent nearly 30 years working on campuses in a variety of student affairs and university advancement roles.  She is often amused by her colleagues, her three sons, the cat which came with the farmhouse she bought, and the cows across the street.  She is less amused by the occasional bear which comes to visit and knock over the garbage can. She may best be reached at

The Defectors (series 2) is sponsored by Presence. At Presence, we’re working to solve all of the higher ed problems you’ve always heard couldn’t be fixed. If you love asking questions, finding solutions to intricate problems, and learning about new people and places, we want you to join our team. Check out our open positions and apply today!