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With the skill-sets and knowledge I had to draw upon, would I really have something cogent and on-point to say to professionals in other fields? As it turns out, the answer is yes, and that fear for the most part dissipated.

-Greg Sadler, Entrepreneur and Proud Defector

In this week’s edition of Defectors in Conversation, I’m really pleased to introduce you to Nicolle, Greg, and Anne.

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Nicolle Merrill (NM) worked in higher ed and Defected twice. First as a Global Programs Manager at Foster School of Business; she left that role for a job as a private jet travel writer in digital marketing at a luxury tourism company. The second role was as an International Student Career Coach in Career Services at Yale School of Management. After two years, she left that to start an online career school for university alumni.

Greg Sadler (GS) is currently president of ReasonIO and editor of Stoicism Today. For about a decade, he worked as a Philosophy professor, and towards the end started moving into assessment, faculty development, and administration.

Anne Scheideler Sweet (AS) spent almost 12 years cobbling together a career in higher ed career while her husband’s military service moved her and her family all over the world.

Get to know them and their wisdom this week in Defectors in Conversation!

Briefly, what got you curious about “breaching the bubble” of your former field/work?

GS: I was already doing that to some extent, simply because I viewed Philosophy as a practical and interdisciplinary activity. So, while doing the typical academic activities – teaching, research, publication, etc. – I was also getting involved in bringing philosophy outside of the academy into more public, practical, and other professional spaces.

I got to make my transition from traditional academia to becoming an entrepreneur and practical philosopher in a more gradual way than many. With each new project, platform, or service I took on, I perceived new opportunities, made additional contacts, and got drawn into thinking about how to make philosophy accessible and applicable for others.

NM: I was curious about [it] for two reasons: I wanted to build more skills and I couldn’t see a path forward. I worked with such good people and had a fabulous boss at Foster; I loved working in international education. But I couldn’t see a path forward.

AS: [In a somewhat opposite issue,] I worked really hard to build a career trajectory for myself and, for a very long time, I wasn’t willing or able to see a way out of the field. I was approached by a friend to consider applying my skills to their family business/startup and decided to take a leap of faith.

NM: When I looked at possible paths to advance I saw limited roles and honestly, just a lot more meetings and too much time spent thinking about budgets. Those options weren’t a fit for me. I was also in program management which didn’t provide many opportunities to increase my skill set. I left for a job that allowed me to build cutting edge skills in digital marketing.

I didn’t think I would return to higher ed but two years later an opportunity opened up at Yale that aligned with my passion for global careers. It was a new role, so I could craft it the way I wanted which appealed to me. I loved that job too. But again the lack of advancement opportunities was a problem. On top of that, there was a relentless focus on MBA rankings at the expense of innovation and change. The rankings game is a common problem in higher education and it preserves the status quo in a time when higher education needs to change. I was curious about changing the traditional career education model so that it better prepared workers for the advances in AI and automation. There wasn’t room for that at Yale SOM (because rankings). So I left for the second time.

Were there any fears at play when you decided to make the jump?

GS: Quite honestly, I had three main fears.

One is the “imposter syndrome” that we’re all familiar with. With the skill-sets and knowledge I had to draw upon, would I really have something cogent and on-point to say to professionals in other fields? As it turns out, the answer is yes, and that fear for the most part dissipated.

AS: Somewhat related to that, my biggest fear was being perceived as a failure for giving up/not being able to “hack it” in higher ed. I haven’t written or posted much about my transition due to still wrestling with those feelings.

GS: Another was almost the opposite of that first fear. Would I be taken seriously as an expert in my field – for example, in my early YouTube videos – even though, in my view, I was practically a “nobody”? I didn’t have a particularly good pedigree, institutional post, and hadn’t published all that much. That fear went away as well, as people responded very positively to the content I provided and the competence I displayed.

NM: [I can understand that.] The first time I was worried they wouldn’t think I was a qualified candidate because program management is not the most competitive skill or a hot job title.

GS: The third main fear was whether I would really be able to earn a living by getting people to pay for my services. That worry is a particularly tough one to get past, especially since some months are lean and others flush when it comes to business!

I was truly confident in the value of working for humans who cared about me as a person and in an environment where changes were possible and encouraged based on what’s important to us as people (kids, family, flexibility, innovation, creativity).

Greg, I have definitely been there…on all three fronts, now that I think about it! Conversely, what were you really confident in?

NM:  I was confident I could create a professional narrative that focused on my communication skills, educated employers about the skills it takes to run successful programs, and convince them that I was a nontraditional candidate to take a chance on. It worked 🙂

AS:  I was truly confident in the value of working for humans who cared about me as a person and in an environment where changes were possible and encouraged based on what’s important to us as people (kids, family, flexibility, innovation, creativity).

What challenges did you have as you adjusted to your new role and new environment?

AS: Still within my first 6 months of the change, so far I’m stumbling over boundaries and time management.

GS: [As a business owner and independent worker,] my two biggest challenges are marketing and maintaining contacts. Both of those are tough to pack into what is always a very busy schedule. The one – maintaining contacts – is actually something I really do enjoy doing, except if I’m feeling embarrassed about failing to keep in touch for a while – and then I have to watch that I don’t fall into that cycle of not keeping in touch, feeling guilty, and putting off getting back into contact until I’ve got the time to write something really substantive. I’ve gotten better about that.

Marketing is still a challenge for me. It’s something that’s absolutely necessary, and I’ve gotten over the “this is self-promotion” hurdle, but I still don’t like to devote time to it. So that is a work in progress.

NM: I had to get used to creative collaboration. I joined a creative team where brainstorming ideas and constant iteration were all in a day’s work. The team was quite flat compared to the hierarchy in higher education. I adapted and loved it eventually but I had to get used to sharing my ideas, getting shut down, building on coworker’s ideas, and working seamlessly with people from diverse skill sets and backgrounds (digital designers, editors, account managers) on one team. Conversely, returning to higher education for a second time after that experience into a non-creative, hierarchical environment was actually harder.

What skills served you well in your transition?

NM: Above all, communication skills. Writing and public speaking are my strengths; I used them a lot during my time in higher education. Lots of people forget the ways you use communication in program management. From engaging students in creative ways to creating documents/resources to presenting on topics, there are so many ways you build communication skills in program management! Those skills are highly transferable and employers value them!

AS: [Case in point:] I’m a shy introvert, so I really don’t love being on the phone, but phone based customer service has been huge for me – being able to talk to anyone and work through an issue together spans all industries. Cleaning up data/records is also a really valuable skill.

NM: Second, my ability to develop a narrative around my higher education experience. You can’t assume employers understand your role. You can’t rely on your job title or your institution’s brand name. You have to explain it to them in their industry language. Show it in your resume, on LinkedIn, in your discussions with people in the industry (hello networking!). A 60 second story that explains what you did in higher education and how it relates to the job you want is incredibly valuable.

GS: As it turns out, one of my talents is for taking complex philosophical concepts from difficult texts, and explaining them so that non-specialists can understand, incorporate, and apply them. I also seem to have fallen into a good balance between maintaining real rigor when it comes to ideas and their application, and engaging with my clients or audience in ways that make them feel valued, not “talked down to.”

What suggestions do you have for people nervous about (or struggling to) articulate their value “on the outside”?

GS: This is where certain approaches in practical philosophy can be very helpful, because that nervousness or difficulty tends to be one of those matters where thought, experience, action, and emotion are coming together in complex ways. Going from my own experience and that of others I’ve discussed this with, fear of rejection holds many people back from making a pitch about what value they have to contribute.

As academics it can be especially tough, since many of us have tendencies to over-explain matters, and to stick with areas we feel ourselves experts in. So sometimes we just don’t make the pitch at all, and we pass up potential opportunities. These are sometimes opportunities to make a connection, a booking, a sale, but sometimes also opportunities to get rejected and develop resiliency about rejection.

AS: For me, asking questions about other people’s work and sharing what I loved about my work was what ultimately led to more serious discussions. I think it’s helpful to learn as much as you can on your own, talk to people on the outside and try things out if you can.

NM: Figure out what you’re good at now while you’re in your role. Ask your coworkers or ask your boss what they think you do really well. Then find a job description or two that interests you so you have a target to work towards. Start by reading job descriptions without talking yourself out of them. Learn the vocabulary of your target job and industry. For example, if you promote programs to students on social media and email, you’re working in digital marketing. If you manage multiple projects and budgets, you’re doing project management. Use a tool like to compare your resume with the job description to figure out if you’re communicating your experience in the language an employer expects.

Then note which skills you need to work on to get the job you want. Find a way to work on those skills while you’re still working! Ask friends in other departments what they’re working on. Ask how you might collaborate so you can build the missing skills.

Finally, talk to everyone. Leave your desk and start asking people about their jobs. What do they like? What don’t they like? What would they do if they weren’t in higher ed? Talk to your friends about their jobs. Then practice telling people what interests you. You need to get comfortable talking about what you want and what you do well. Start small. Practice saying things like, “I’m interested in digital marketing because I’ve have really good success running our social media recruiting campaigns at UW” to people you meet.

The more you tell people what you can do, the more confident you get, and the more people can help you.

Start by reading job descriptions without talking yourself out of them. Learn the vocabulary of your target job and industry.

Special thanks to Anne, Greg, and Nicolle for sharing their time, energy, and wisdom with me for this series.