Interview with a
Barefoot Writer: Ted Capshaw

Ted Capshaw

“Stop living the unknown and stop allowing these narratives you’re creating in your head to prohibit you from moving something forward.”
— Ted Capshaw, Organizational and Individual Change Agent

Emotional Intelligence (EI), or the idea of being able to identify and manage your own emotions and the emotions of others, has become ubiquitous in the entrepreneurial and business worlds. Ted Capshaw is among those rare professionals who not only recognize the importance of EI, but also help others develop their own.

With a background that stretches from overseeing budgeting and human resources to teaching entrepreneurship and various other consulting and counseling roles, Ted’s focus is on creating organizational change by improving leadership. He does this by highlighting and facilitating positive change for individuals.

Ted is also a dedicated family man, volunteer advocate, pro bono consultant and board member for several non-profits, and has been a mentor for organizations such as Big Brothers Big Sisters. He also blogs on his personal website, His hard-hitting insights are valuable to writers in that they will challenge you to be greater than you thought possible, and to recognize the power of accountability, particularly as it relates to the meaningful pursuit of your writing dreams. Take particular note of his advice on achieving success without burnout, what it means to “stay true” to yourself, and why you should embrace your fears as you move forward in your writing career.

When you were younger, did you dream of coaching people like you do now?

I don’t think I dreamed of becoming anything when I was younger. I was just trying to make it through. I think as I got a bit older, probably in high school, I’d have to say my dreams were not my own. The dreams projected on me were those that others expected of me … like many people. I don’t think it was until my early 20s that I started to think of myself as becoming something.

How did you come into your present role of helping develop leaders and improving organizational culture?

My childhood surely had its challenges. I grew up in a blue-collar neighborhood. The love I received within my multicultural home was not always matched outside of it … it was confusing. When I say I was trying to make it through, I mean I had a lot of trouble in high school. I got kicked out of high school and wound up going to an allboys school. I think I was just trying to figure out what I should do, and really, was simply trying to be accepted. They said I should go to college so I ended up going to college.

I eventually took a job as a junior high school counselor, which I really enjoyed. I spent a couple of years in that position. Then I took a job at a nonprofit for a couple of years. At that time, I thought I wanted to go and get my doctorate degree like my father and eventually become the mayor of Minneapolis. Then, unfortunately, I lost my father.

That’s really where everything transformed and where the journey began to where I am now. After I climbed out of the hole and a three-year depression, I started thinking that one day I wanted to do what I’m doing now. I remember thinking to myself, though, that I had no credibility. I was about 30 years old and wanted to do this work. But how does somebody like me gain credibility in front of these people? So I switched scenes, and thank God, I found this client who approached me and said, “I’d like to hire you.” I’d never heard of them and didn’t know what that company was or what their expectations were, but that’s where the journey began. I was about 31 or 32. I remember thinking, “I’m going to spend my thirties really learning, and I’m going to be of value.” And I did just that.

And that felt like the right path?

I think that I’ve always loved people and always wanted to work with them. I’ve always had empathy for others, but I don’t think I had the maturity to perceive that part of myself. But losing my father helped me develop into who I am today, where I want to see people follow their passion and dreams. I want to help people get to a higher place before tragedy. I don’t want people to wait for tragedy to hit, as I did, and to live the life they truly want.

How did you get started?

I spent time trying to learn about culture and people, so I purposely stayed at my existing job as Chief Learning Officer for two years. Then I took a job at a nonprofit as COO. Again, I was trying to learn how to line up work and about operations to give myself credibility. Interestingly enough, my best friend used to tell me, “You need to be in the circuits, you need to be on the road, you need to be empowering people.” I said, “Maybe one day.” Then when I turned 40, I incorporated. I still had a job, but I wanted to see if I could add this big venture and eventually do it full time. I wanted to stay true to this work that I do with people and try to get the message out.

So you went for it?

Right after I incorporated, it took off. I jumped off the cliff and left my full-time gig. I actually did it at a crazy time — my wife was pregnant with our first child. But I wanted flexibility, and I wanted to be a father and a husband more than anything else. I thought that if there were ever a time to do it, now was that time. It was a little risky, but I thought what I really was changing was flexibility, and that I’d be able to do the work I love on a deeper level. I knew it’d be valuable, but I didn’t know if I’d be able to get clients. I didn’t know how people were going to perceive what I had to say. But here I am, five years later, making ten times more money than I ever thought to make and with people calling me every day, all day, for solid advice. And more importantly, with the flexibility to be the husband and father I want to be and staying true to my core work.

One of your core messages is “Stay true.” How can someone be fully present and true to themselves in our current digital age?

When you get on Facebook or social media, you know who’s fake. You know what they’re putting out isn’t real, and that it’s positioning. So I suggest you ask yourself, “Are you drawn to that person?” Nine times out of ten, you’re not. Then suddenly you come across someone who means something, and the person seems truly authentic. For whatever reason, you come back to that person, and you’re drawn to that person. Listen to your gut reactions regarding how you are presenting yourself digitally. Are you being authentic? Are you staying true? How do you think others perceive you? Are they drawn to you?

What’s your reaction to the advice to “fake it till you make it” when trying to get started in a new profession?

I just do not believe in that. When I stepped out on my own, I had people coaching me to fake it until I made it, like telling people that I have clients all over the world or giving people a false sense of how much money I was making. I was even told to get a custom-made suit so that when I met with a client, they’d know I make a bunch of money. But that wasn’t me.

What’s your approach instead?

Even today, making the money I make, I pull up to my clients in a four-cylinder Honda, and I’m “me.” What I hear from my clients in return is how much they appreciate it and how much allowance I’ve created for them to be vulnerable with me.

So whether it is social media, writing, videos, or whatever you’re doing, speak honestly and with sincerity. I think people see through the bullshit, and I think people are screaming for authenticity in our world today. I never thought I’d be evidence of it, but I am 100 percent evidence. I went out there, I stayed true to myself, and I presented myself. When I’m giving a talk, sometimes I get up in front of the room and read poetry, or I play music to get people to sing. I leave myself vulnerable in front of the room. The result is that people connect with it. I was scared at first. I didn’t know if people would embrace it, but the feedback I’ve gotten in the past five or six years is that it’s my honest approach that keeps people calling me back.

What’s some of the best advice you’ve ever been given?

I think the world, my life experiences, and my hardships have taught me far more than I learned in school. As a matter of fact, my father, who was a college president before he passed, used to tell me tha tschool was 70 percent life experience and 30 percent books. I never grasped what he was saying until he was gone, and then it started to make sense. So be a student of life, feelings, situations, and people. If you read the “About Me” section in my blog, you’ll get a glimpse of what I mean.

You launched a blog via your website about a year ago. Where do you find inspiration for your posts?

I’d say from a variety of places. They are my own internal things. I really set out to create a platform where people felt allowed to connect and be real about the things in their lives. Through my work, I found that so many people live in the same space of insecurity, pain, and fear. The posts really are just past and present truths and lessons in life and leadership that I experience and attempt to transform into lessons for other people.

You do a lot of volunteer work. How has that affected you?

I think it just helps me keep things in perspective. I always tell people, “The wonderful thing about giving is that it’s you who gets the true gift.” I find that time and time again. Anytime I slow myself down to truly give back in a way that I don’t do on a day-to-day basis with my work, I just feel wonderful. Also, whenever I leave an experience where people are working with inner-city kids or whatever, I leave feeling humbled and grateful.

You have two young boys, ages two and four. How will you teach them to be authentic and to follow their dreams in today’s world?

I don’t think there’s a better way to teach them than to live by example. But I don’t think it will be as much about me teaching them as it will be about me allowing them to be who they are. I will not raise my sons to be the bravado man. I’ll allow tears, I’ll allow the exploration of different things in their lives, and I’ll never push them into a sport or to play piano. When they come home and tell me they’re afraid of something, I’ll completely listen and will never explain that I understand, because I don’t. I’m not in their shoes.

I think the biggest thing for me, and it’s something my father handed down to me, is that you never should claim to understand. To this day, I can still feel and picture his arms around me. However, he never said he understood. I think that was probably the most valuable thing he did for me because he allowed me to experience different things on my own, yet I always knew he was there. So I believe the biggest thing with me, with my two boys, is creating an allowance for them to be who they are and making sure they know I love them and support them.

Writers feel that pressure, too, where they worry about positioning and face pressures to go in a certain direction. But it’s really about putting an authentic voice out there that leads to success.

There are people out there who want to connect with you, you just don’t know it yet. Your voice has a space out there somewhere. If you have ability and you can articulate yourself as a good writer, I think people will see that for what it is.

And that’s not just true in the writing world. Like I said, the majority of coaching I received when I stepped out on my own was to do things like get a custom-made suit. I also had somebody tell me to get an expensive pen so that when I signed a contract I looked serious. There is that whole “walk in the door and look like you make a million bucks” idea so people think you’re credible. But I believe in the human connection much more than that, and my belief has been affirmed by the income that has followed that approach.

What’s your advice on how to manage time to pursue writing goals without sacrificing what’s really important?

Focus, focus, focus. I tell people all the time in corporate America that if they could get four focused hours in each workday, they’d be more efficient and the company would be more profitable. People aren’t focused; they don’t approach their day with purpose and an understanding of what they’re trying to accomplish. The other part of that is to remind yourself each morning why you’re doing what you’re doing. If I have to pick up an extra client, I’m busier than normal, but I understand what I’m trying to do. I’m creating flexibility for my family; I’m providing for my family.

I do think you have to understand that your time is valuable, but I don’t think it’s just about time, which may be contrary to what a lot of people say. Many people told me I would have to work 12- or 15-hour workdays, but I haven’t worked a 40-hour workweek since I incorporated. It’s a little more relevant in a corporate setting because of all the nuances that happen in an office each day, and I understand most freelance writers work at home. However, I think working at home is even more difficult because you’re there with all the distractions and the things you’d rather be doing in your home. So the question still is: are you getting those four or five focused hours? Always keep the main thing the main thing.

What about would-be writers who are afraid to put themselves out there?

I wouldn’t tell them to move past their fear. I’d tell them to embrace it, to truly understand the fear. Again, it goes back to the allowance of it. One thing I’ve found, particularly in the past six years as I jumped off the cliff and spend every day with people, which is such a blessing, is that we’re all in the same boat.

Whether it be the chief of staff in the governor’s office here, who I’ve coached, or a CEO, or whoever, we’re all drowning in fear. I’ve yet to meet an exception. When I have met a supposed exception, usually within two or three sit-downs, I’ve broken that person down and revealed that they’re just presenting the world with a façade. So I don’t think it’s about moving past the fear. I think it’s about embracing the fear and understanding it as part of the process and letting it motivate you. For my fears, my wife will say, “You’re so paranoid all the time,” and I’ll say, “I think it’s a healthy level of skepticism because I know it’s going to take just as much extra on my end to continue this thing.” I rarely coach people to just move past their fear because the truth is, you may go in front of five clients, and the fear might get bigger, because the next level of fear is, “How are you going to sustain it?”

Then how does one work through that fear?

I’d say just do it. Jump off the cliff. Again, I’m drawing from my own experience; I just did it. I didn’t know if I was going to land. I didn’t put together an elaborate manual, I didn’t put together fancy contracts of what I was going to do — I just did it. I recognized that the fear was merely a part of it. I think part of the problem is that so many of the fears that we have are narratives in our heads. Unfortunately, those narratives are based on the unknown.

But it’s not good to dwell on the unknown. Where does that get you? You don’t know if someone is going to resonate with something you write. And if you don’t know, you sit there and wallow in the unknown. You won’t ever know until you go out and do it. It might fail, but my advice would be to stop living the unknown and stop allowing these narratives you’re creating in your head to prohibit you from moving something forward. It’s simply unproductive to live in the unknown, yet we do it all the time. We constantly speculate, and it’s crippling.

I talked to a buddy yesterday. In the past, neither of us had any money, and now we both have money. We’re sitting with a safety net and money in the bank, but the fear is almost worse than before. There’s a fear that it could go away. The fear in the beginning is a bit different than the fear we have now, but it’s still fear, and if you live in it, it’s just crippling. I don’t think fear ever goes away.

So you’re saying people should recognize and honor their fears?

Yes, and recognize them in others. For example, if you’re working with someone who has a strong personality or who comes across as an extremely forceful person, start by trying to recognize their insecurities and fear. It shifts the dynamic, and if you change your approach with the person and be a little empathetic, you’ll see results damn near immediately.

How can a writer who works virtually build a support network that matters?

Figure out what kind of support you think you need. For example, I have a variety of people whom I either sit with or call for support. I have a couple I call almost daily; I have another one here in Baltimore where we have a monthly sitdown called “Soul Check.” It’s all about making sure we’re doing what we said we were going to do. Do you have someone that is holding you accountable? Then I have someone I reach out to for financial and business stuff. I don’t think there’s an end-all, be-all person or a network of people. For me, I’m not a real social person so I don’t like networking or that sort of thing. I do have about four or five people who see me and support me in different ways. They’re all very important to me, and I recognize in myself what I need.

How does someone get to that point?

You have to understand yourself and perform a self-audit. What do you really need? Then, go seek those people out. The second part of this is you can’t be afraid to ask for help. I think you’ll be surprised that people actually want to lend a hand. Often times we don’t ask for help or build those relationships.

We think, “Oh, he’s not going to have time for me. He’s too busy, and he’s a good writer. What’s he going to want to do? Why would he want to spend a few minutes with me asking questions?” They do not understand that every person on the other end has an ego and probably wants to feel worthy of helping somebody else.

What kinds of things make you laugh so hard you clutch your stomach?

That’s easy — my boys. Particularly now, my four year- old — the things that come out of his mouth. Or my almost-three-year-old acting as if he is Hulk. Goodness gracious. Like how excited they get to see a duck. I could go on and on about the belly laughs, but I don’t know if I’ve ever laughed as hard as I have since I’ve had kids.

How would you advise freelance writers to pursue success without getting burnt out along the way?

I think burnout comes with what most people equate burnout to, which is not having enough time or money or that sort of thing. They’ll make it about time because again, I think they lose focus. I think in today’s world, far too many people think that it’s all about time. For example, that they must put in a certain amount of time on a task, or if they don’t stay that extra hour at work, then they won’t be valued as much. I think the problem is that people aren’t putting enough focus into their day. I think focus is what prevents burnout, along with what is so commonly said, but not commonly practiced, which is to create balance. You tell people to create flexibility in their lives and find freedom and balance, yet suddenly, they find themselves imbalanced. I tell CEOs and leaders the same thing all the time, “You guys are preaching this, yet you aren’t practicing it yourselves.”

I don’t know if there’s a better answer than focus. Don’t work more than you have to, live a balanced life, take care of yourself, and all of that. And don’t compare yourself to other writers. That goes back to when someone really doesn’t understand the “why.” They don’t understand why they wanted to get into this profession of writing. They forget they wanted more flexibility, and now they have more flexibility, but they’re not making the money. Then say they make more money, but now they’re not making as much as the next person, so they’re comparing themselves. They’re not reconnecting to why they got into writing in the first place, which I think leads to burnout because they’re trying to keep up with the Joneses. Good luck with that.

What advice would you give writers who are just starting out?

I would tell people to look for a completely different set of characteristics within themselves. Characteristics that build a platform for relationships … like sincerity, vulnerability, honesty, and grit. A lot of people just go by what’s on their resumes. What they should say in an interview, and what I’m telling people to look for, is the desire to make it. If they don’t have the experience, but they articulate that you should pick them because they have this desire, are willing to learn, or have a good work ethic, and so forth, it’s more authentic. I think people today appreciate vulnerability. As scary as it is, and I do think it’s extremely scary, it’s important to say, “I don’t have as much experience as the other guys who are applying for this, but this is what I do have.” Couple these things with being a competent writer and BAM!

If you'll be at FastTrack to Copywriting Success Bootcamp and Job Fair this year, there's a good chance you'll get to meet Ted in person. But if you're not signed up, be sure to get your name on the waiting list now!

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Published: September 5, 2017

1 Response to “Interview with a Barefoot Writer: Ted Capshaw”

  1. I heard Ted speak at last year's Bootcamp, the last speaker of the camp, and was so impressed by what he said. And here it is again, his valuable insights into the whole process of what we're all trying to do here at AWAI, I think he really hits the nail on the head. Thanks for the inspiration, again!

    Mary Kay SealesSeptember 6, 2017 at 12:24 pm

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