Dewayne’s Winding Path

I’ve come to know Dewayne White recently through a friend who ran a veteran’s organization.  He made the move from serving in the Army to becoming a stand-up comedian. Dewayne, 48, resides in Woodbridge, VA. He received his BS in Liberal Arts and an MS in International Relations.


Who is your current employer(s)? Me!!!!! Although, I do have a side gig where I teach leadership, but it’s very part-time. I teach w/ a small government contracting firm, Clarke Consulting.  Our students are mostly Navy civilian employees.  It’s not a necessary thing revenue-wise, but it certainly helps.  I mostly do it because I enjoy it a lot, and the company gives me the freedom to have this be my “side gig.”  We talk a lot about creativity, problem solving, taking care of people to get more accomplished, etc.  I didn’t have that job until after I quit my government job, actually.  What I think is interesting is that a) I got the job BECAUSE I was a standup comedian (in addition to meeting the requirements).  They wanted someone who could hold an audience’s attention.  b) It dropped into my lap AFTER I made the decision to leave the government.


In two-three sentences how would you describe what you do most days/weeks?

I perform in comedy clubs & bars throughout the country.  I also produce comedy shows and open mics throughout the area.  I run shows at a bar in Woodbridge called The Electric Palm (every Tuesday open mic, every other Friday ticketed shows, and every other Wednesday we do a “riff” mic where comics have no idea what they’ll be talking about..topics are drawn out of a hat.)  The mics allow comics to work on new material and the shows allow newer comics to perform a bit longer sets in front of a great audience while also performing with seasoned comedians. 


What did you want to be when you were eight?

When I was 8 I thought I wanted to be a professional wrestler.  I started wanting to be a comedian when I was about 10.


What did you learn about work that you learned from your family? 

Mom taught me to work hard, like REALLY hard.  She had to hustle all the time.  In a lot of ways, she works too much.  But, I learned to make my own way.  Dad taught me to always have fun.  He was great at leaving work at work (he was a prison guard, so that may have made it easy).  My grandfather and grandmother (on my Dad’s side) were ministers and they taught me to take care of people and create a family wherever you happen to be.


What professional experiences/employers had the greatest impact on you?

The Army had the biggest impact.  I NEVER planned to do a career in the Army.  But it really taught me that if I worked hard I really could do anything.  It’s a great place to grow and experience new things (living abroad, learning a language, getting an education).  It made me a LOT tougher (I was a drama guy in high school and weighed 130 lbs when I joined).  My first contracting job after the military I had a great supervisor and mentor.  He was actually younger than me, but I distinctly remember him telling me on the first day of work, “you’re not in the military anymore. You don’t have to work for free.”  He was basically telling me that my time belonged to me now, and people couldn’t dictate what I did and when I did it like before. 


What is something about your career journey that people might not expect?

EVERY person in my house has said at one point, “All you care about is comedy.”  They’ve all thought I was nuts, and in the beginning wanted me to quit.  Then, they realized…he’s serious. And he’s actually good at it.  This isn’t a hobby.  When they realized that, they came around and really started to support me 100%.


Why did you pivot?

I was miserable.  I couldn’t do the government thing anymore.  I really started seeing my job as getting in the way of what I truly wanted to do.  I hated going into work every day.  Even during the pandemic I would sit up at night and dread opening my work computer and “going to work.”  I had gotten to the point that I was depressed because I knew I wasn’t where I was supposed to be.  Yes, it paid the bills, yes it was “important.”  But I hated every second of it.  And I knew I was doing a job that lots of people wanted.  But I knew it wasn’t for me.  At all. Important in the sense that it was strategically important.  It was nuclear weapons inspections.  So, to the government, they’re extremely important and critical things.  For me, I had grown very tired of that life.


What skills were portable from what you had been doing previously and what was brand new to you? 

I gained a lot of skills in the military that were helpful.  The obvious ones like discipline and hard work.  Never quit attitude, etc.  But, also..the military is a very funny place.  People are constantly joking around.  You have to in order to keep sane sometimes.  Things like combat, difficult training, difficult situations lead to stress and comedy helps alleviate some of that…or at least make it manageable.  Another thing that I think helped with comedy is public speaking.  I was in a lot of jobs that required me to put myself out there and speak publicly (Russian interpreter and later a team chief, instructor at West Point). Another thing that helped was the leadership I learned in the army and the gov’t.  I see this as I try to “take care” of new or young comedians.  I try to form a team or a family out of the ones who I work with regularly.  An example is Thanksgiving.  I used to have Soldiers who weren’t going home for Thanksgiving or Christmas over to the house.  Now I try to do it w/ comedians.  It helps create a bond and a brother/sisterhood between us instead of just being a bunch of individuals.  As far as new skills, I think it was more of dealing w/ people with a much different mindset than me.  In the military and government people are more diverse than most think, but there is a common thread of “do the right thing, follow the rules, etc.”  Now, I deal with artists.  They think differently.  They’re often more open and free with ideas and rules.  They may not show up on time (though the good ones do).  It takes a bit of getting used to the different culture.


What was the hardest part about making a career pivot?

Losing the security I had, without a doubt.  I was an Army retiree, and was now in the government system where it’s nearly impossible to get fired.  I was set.  No worries about money.  It was difficult to see that it would be ok without that guaranteed paycheck.  It was especially difficult to take the step because a) I grew up poor, and was terrified that I’d go back there  b) My wife doesn’t have a job, and c) I had one child in college and the youngest is about to start.


What were the most important lessons you’ve picked up along the way?  

  1.  It’s going to be ok. I was paranoid that I was going to end up homeless, broke, and ruin my family members’ lives.  When I really took a step back, I was actually in a much better position to take that step than I thought. 
  2. Being happy is worth SO much more than money. 
  3. Things drop into your lap when you least expect them.


What would you say to others who are doubting their ability to make a change in their career/vocation?   

Take a realistic look at where you are and see how you can take small steps to accomplish the goal.  But, don’t doubt yourself.  The hard work you’ve put in to be successful where you currently are will help you in your future undertakings, too.


Where did you get the confidence and support to make such a change? 

My wife certainly helped me.  At one point, she realized that I was beyond unhappy and not “complaining to complain” which is something we do in the military.  She realized that I was miserable.  She told me one day that she’d do whatever it takes to make it work.  If that meant get a job, move, whatever.  That helped a lot.


The other thing that helped a TON was Cognitive Behavioral Therapy through the VA.  My therapist and I worked out a step by step system to get to my BIG goal of leaving my job and doing comedy full time.  It literally began with VERY small stuff like “go to a restaurant you haven’t been to” or “order something different” in order to get comfortable in unknown circumstances.  Once I did some of the smaller things, it was actually quite easy to leave my job.  In fact, it had been a couple of weeks since my therapist and I had met, and she asked me, “so, anything happen recently.”  I replied, “Well, I resigned from my job.”  She was very surprised because I was only on step 3 of about 15. 


What was the hardest thing you had to overcome in your professional life? 

Being comfortable in uncomfortable situations.   I was a shy, dorky guy in high school, so I wasn’t really what I would label as the “Army guy.”  But…I ended up loving it..even the physical stuff, the hardships, the being dirty, moving every couple of years, making new friends VERY quickly, relying on strangers, etc.  I learned that I could operate without sleep or food or comforts way better than I thought.  I think that’s something that helps me even in comedy.  I also have a drive that I don’t think I would have had if I wasn’t a military guy.  I know that if I work hard at something, I can be really good at it. 


What is something about your career journey that people might not expect?

I think people don’t understand how hard comedy really is.  Because they see someone get on stage for a short period of time and just “be funny.”  But, it’s so much more than that.  It’s thinking, writing, editing, networking, editing more, business “stuff”, editing, etc.  I read a study once that said it took 23 hours to develop 1 minute of “A-level” material.  I honestly think it’s more.  It’s important for many reasons, but most importantly, so that people who watch comedy can gain a new respect for the art form and the effort that the comedian you’re watching on stage has already and is putting in.  That’s not necessarily unique to my journey, but it is something that I don’t think most people grasp.


What, if anything, are you hoping happens next in your professional life?  

My main goal right now is to get on the touring comedy club scene.  I’ve started doing it some, and that’s (at least for now) where I want to be.  Some people are shooting for theaters and stadiums…and, maybe, but I love the vibe of comedy clubs and that’s where I want to focus my efforts in the next year or so.

Russ Finkelstein [] is the opposite of your High School Guidance Counselor.  A career coach, social entrepreneur, and advisor to founders, he is currently the Director of Coaching with the Roddenberry Fellowship, Coach-in-Residence with StartingBloc Fellowship, and a Co-Founder of Title8 a Legal Marketplace. He was a founder of the noted careers website and was chosen as a Generation Z Influencer by LinkedIn.

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