Career Design Talks: Question Your Assumptions To Design A Fulfilling Career

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This is part of a series of conversations I have with interesting people doing interesting things. My goal is to tease out the lessons learned during the ups and downs and twists and turns of their career journey so that you can gain ideas and inspiration on how to design a fulfilling career.

Every major transition in my life where something amazing happened to me, happened because someone else believed in me and encouraged me to go for it.
— Will Wise
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Will Wise is the Chief Weologist at We! A company on a mission to create conversations that matter. Leaders call them when there is a lack of trust getting in the way of results. They lead workshops and company retreats for Fortune 500 companies, non-profits, startups, and educational institutions with a focus on improving relationships, group dynamics, and team performance by teaching people how to ask powerful questions.

He has over two decades of experience building leadership programs which has earned him a reputation for being someone who can transform groups and individuals into their best selves. Most recently, Will has added author to his list of accomplishments with the release of his new book, Ask Powerful Questions.

But his road to becoming a sought after speaker, consultant, and trainer was anything but a straight line. In this conversation, we talk about where he started his career as a Peace Corps volunteer in Nepal, what career advice he would give to his younger self, and how he likes to challenge his leadership students to find their own style of leadership. 

Q: You started your career as a Community Forestry Volunteer with the Peace Corps in Nepal. What drew you to Forestry and what did you learn from that experience?

A: As a kid, I always found comfort and solace in the woods near my house. Growing up I always felt like I didn’t fit in anywhere, whether at home or at school or based on what media and culture told me I was supposed to be like. So I felt like I had to do my best to fit in to gain acceptance. And the only place I got any comfort and felt I could just be myself was in the woods behind my house. And when it came time to think about a college major my father suggested I try forestry. I had no what that was at the time but decided that it sounded like a good path for me. And when I graduated I found the Peace Corp opportunity and fell in love with the idea of being part of a community in Nepal that was connected to preserving the earth.

Q: Once you completed your assignment with the Peace Corps what did you do next?

A: Well I actually didn’t want to leave Nepal. In fact, I asked to stay on and continue working there but they didn’t need me. I traveled around Asia for a bit then explored the western part of the US and eventually heard from a friend who said that she had the perfect job for me back on the east coast and she was right. It was a job leading outdoor education and team building programs for a group called Nature’s Classrooms. What I loved about that job was that I could teach what I wanted to teach based on whatever I was interested in. And in that job, I got to practice my teaching and speaking skills and got better at understanding how to communicate my message to different groups of kids. If something didn’t land I would try it another way. I became comfortable with trying and failing and learning and luckily it was a low-risk environment where I couldn’t screw it up too much.

Q: What motivated you to live a life where you traveled so much?

A: I’m an insatiable learner. I’m curious about anything that’s different from me. But I grew up in a family where both my parents had stable full-time jobs with benefits and had a safe daily routine they stuck with. And I was always conflicted about what I should do. Should I do the safe stable job thing or should I try new things? While I was always scared to take a risk and do something new, as I think back every major transition in my life where something amazing happened, I had someone else who believed in me and encouraged me to go for it. I leaned into that fear and something phenomenal always happened. I also worked odd jobs throughout college which allowed me to graduate with zero debt. So that gave me the freedom to choose the less conventional path.

Q: How does an unconventional life of work and travel lead you to run leadership and communication programs at Penn State University?

A: Well the short answer is that I met a beautiful girl who is now my wife and I followed her to central Pennsylvania. One day she took me to a party I didn’t want to go to where I met the Director of the Race Relations Project which is an organization that facilitates conversations around taboo subjects like race, gender, and conflict. We talked about my experiences facilitating groups and creating experiential programs and she invited me to come and observe one of her classes. After that, I joined them first as a consultant and eventually, they offered me a full-time job. And sure enough the fear came up again and I was asking myself the questions of “Is this what I want to do? Is this where I want to be? Could I make a difference here?” And that was over 11 years ago I’m still here and we’ve grown the program.

Q: When you look back on your career what lessons can you share about doing what you love and finding fulfilling work?

A: The advice I would give to my younger self would be to play with the idea of work and reiterate. Try things, explore your curiosity and do it in the real world as much as possible. Get away from your computer screens and get real-world experience as much as possible. Take a class, go to a conference, volunteer, talk to people. Question any assumptions you have about what work should be, and make adjustment as you go. Because for me, while I did play with the idea of work, I also felt the pressure to have the full-time job with benefits. I was always seeking that because I thought that’s what I was supposed to do. But if I could have fully given myself permission to play more and question my assumptions and do what I wanted to do who knows where I would be now.

Also, don’t get caught up with the idea of following your passion. When I was 20 I had no idea what my passion was. Back then I was interested in trees but now my work focuses on people and relationships and building trust.

Q: As a leadership development trainer what do you think people can do to improve their leadership skills?

A: I think a common mistake is that people think leadership has to look a certain way. They think they need to be perfect and have all the answers. As I train leaders I like to get them comfortable with trying new things and failing and eventually finding their own style. I can give them a framework but I don’t want them to do it my way. I want them to lead their way. I want them to be aware of their strengths and weaknesses and develop a style that works for them.

Q: The title of your new book is “Ask Powerful Questions”. What is an example of a powerful question one can ask themselves when thinking about their career path?

A: If you’re exploring a new career path it is important to know what your strengths are, what you enjoy doing, and what you’re good at. But in my experience when you ask someone directly what their strengths are or what they are good at you get a sort of sheepish “I dunno” response. So a question I like to ask someone around their strengths is “Think of a time when you accomplished something you were proud of at work. How did you contribute to that?” And all of a sudden they are looking at their performance with a new lens and they start to come up with a list of activities they did that contributed to their success. 

Also question your fear around whatever is holding you back in your career. Ask yourself “What am I really afraid of?” Are you afraid of failing? Are you afraid you won’t find another job? Are you afraid of what your parents will think? Once you can identify the reason behind your fear you can assess how real or imagined it is and take practical steps to combat that fear so you are no longer paralyzed by it.


If you enjoyed this interview don’t let the conversation stop here. You can learn more about becoming a better communicator and leader by checking out Will Wise’s book “Ask Powerful Questions” available on Amazon.

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If you would like to learn how to design a more fulfilling career you can download the Career Design Guide below.

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