The Psychology of Doubt: 13 Entrepreneurs Talk About Overcoming Insecurity

Welcome to the official launch day of Zen Psychiatry!

Today is a big day for me for a couple of reasons. 1) My blog relaunchs (yay!), and 2)  A few days ago I finished my 2nd year of psychiatry residency, which will usher in a big change for me in terms of schedule, lifestyle and overall happiness with work.

No more overnight call, no more inpatient wards, and no more of me pathetically sobbing to myself on the way home from a 30 hour shift (I hope…).

Those of you who have followed along with me here know how tough the last few years have been. On a regular basis I questioned that I had chosen the right career. I doubted that I could make it through and come out okay on the other side.

But I made it! And I can say definitively (with the perspective of knowing the hardest days are behind me) that I have chosen the right path, I am in the right career, and that I’m so glad I didn’t give up prematurely.

Reflecting on this recent milestone inspired me to reach out to a few of my favorite entrepreneurs and ask them about their experiences overcoming doubt, because no one knows doubt like entrepreneurs.

While becoming a doctor is tough, the steps you need to get there are clearly laid out. Do well in college, take pre-med classes, go to medical school, choose a specialty, apply to residency, etc.

The same can’t be said for starting or running a business. When you’re an entrepreneur, sometimes deciding what is most important to focus on is just as hard as doing the work. And sometimes the biggest barrier is getting over your insecurity to take action, even when you’re not sure things will work out.

So I got in touch with some of my favorite entrepreneurs, all people I personally follow and admire, and asked them a simple question:

When was a time when you faced doubt to build your business?  How did you break through the doubt to accomplish your goals?

Their strategies for dealing with doubt are inspiring and diverse – everything from surrounding yourself with the right people to learning to ignore the doubt to asking for help when you need it. A common theme: doubt isn’t something you overcome once, but rather a challenge you surmount daily.

Enter the entrepreneurs. Not all of them own businesses in the traditional sense, but they’ve all learned to get past their doubt to create something insanely helpful, useful or meaningful for other people. I hope you find their responses as inspiring as I did!

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Corbett Barr, Think Traffic, CorbettBarr.com

Quick intro: I am a huge fan of Corbett – he is one of the first bloggers I came across in the lifestyle design niche, and he’s always impressed me with the honesty and sincerity he communicates online plus his business skill (a rare combo). He’s structured his work such that he spend several months a year living on a surf beach in Mexico – obviously right up my alley.

I face doubt daily. Not sure if that’s normal, but I’ve accepted that I have to overcome doubt every day in order to get anything done.

To get past my doubt, I try to psych myself out with the “what’s the worst that could happen” question followed by the “do you have a better idea” question. I know that action is the key to getting anything done, and doubt is the #1 action killer, so getting past doubt is critical, no matter how you do it.

Scott Dinsmore, Live Your Legend

Quick intro: Scott started off writing at his blog Reading for your Success, but then discovered his true passion wasn’t writing about books, but instead helping others find work that makes them comes alive. He rebranded and relaunched as Live Your Legend, and now has helped thousands of people quit their jobs and find work that is meaningful to them.

The biggest time I faced doubt related to my business was two years ago when I was considering shutting it down because it was going nowhere. But then I started to hang around people who had done really inspiring and amazing things in my space. It completely changed my psychology and belief about what was possible.

The fastest way to start doing things you don’t think can be done is to hang around people already doing them. Brainwash the impossible. This has been the most powerful doubt-removing limit-crushing practice of all. Everything comes back to environment.

Sibyl Chavis, The Possibility of Today

Quick intro: Sibyl is a former attorney who underwent a 40-day experiment to stop complaining, which inspired her to start teaching others how to live each day fuller than the one before. She quit her cushy job as a lawyer (which takes guts!) and now writes and manages The Possibility of Today full time.

Right after I jumped and quit my job to build The Possibility of Today I had a lot of doubts and a good amount of fear. It just felt right though to jump despite all of the fear and uncertainty.

Nevertheless, I knew I was going to need to overcome those fears and create a “success mindset.” The way I decided to do that was by doing “mindset pushups” every single day.

One of my favorite sayings that I really tried to keep top of mind was “Your dreams are your possibilities.” Every time a doubt or fear would surface, I would remind myself that everything I wanted to create was absolutely possible. I did this over and over again and just focused on doing everything I could to take step forwards. Eventually, my confidence overshadowed my doubts.

Ashley Ambirge, The Middle Finger Project

Quick intro: Ashley is the sassy copywriter behind The Middle Finger Project – seriously, just read a post or two on her site and you’ll be hooked like I was. She’s translated her mad writing skills into numerous products and services that help others improve their own businesses. Dig around her about page to read about the challenges she’s overcome, which makes her success even more inspiring.

I remember a distinct period in time when I faced mega doubt–not in the business, but in my ability to manage all of the tasks and responsibilities. Things ramped up so quickly I wasn’t logistically prepared for it, and it caused a lot of overwhelm and anxiety–which is never a breeding ground for a healthy business!

I knew I needed to hire someone on, which was also a scary process because I hadn’t done before. Fortunately, I’m good at big picture thinking, and I knew that if I wanted the business to grow, I needed to get the hell out of my own way.

Tyler Tervooren, Advanced Riskology

Quick intro: A few years ago, Tyler was laid off from his job, and instead of rolling over and giving up, he started his blog to show people how to live better lives through taking smarter risks. He created the 1% Club to showcase his journey to pursue challenges that 99% of people will never do, such as run a marathon on every continent (including Antarctica!).

*A* time? Ha. I feel like I face some type of doubt almost every day. And I think that’s how I get through it as well—realizing that I run into it every day, move past it, and the sun still rises the next day.

Some problems you have to face head on and deal with, but doubt is a different story, I think. Doubt is one of those things that’s best ignored. If I pay any attention to my doubt, it tends to build and get worse. But if I do my best to just ignore it and push forward, then it fades away and life goes on until the next time.

Tammy Strobel, Rowdy Kittens

Quick intro: Tammy started writing at her blog to share her story about downsizing, and now is a go-to source for inspiration and practical advice for living simply. Like, really simply – she lives in a tiny house (128 sq ft) with her husband Logan. She talks about going car-less, keeping a writing habit and maintaining a very small business.

Stepping out of my cubicle and starting a full time writing business was the hardest part, but I face fears everyday. The key for me has been to keep trying new things.

For example, I decided to launch a writing ecourse this summer and I took one tiny step everyday to make it happen. Taking small steps to grow my business doesn’t feel overwhelming and that helps me break through self-doubt and accomplish my goals.

Derek Sivers, CD Baby, Anything You Want, Sivers.org

Quick intro: Derek might be an anomaly in that he’s the only entrepreneur I talked to who said he never faced doubt in building his business(!). He also created the hugely successful CD Baby, which he sold in 2008 for $22 million, donating almost all to a charitable trust to support music education. He argues that filling a need is the most key compoment to starting a new business.

Sorry I can’t help with your question. I never had any doubt.

See… CD Baby was started only because I had people asking me every day if I could sell their CD for them. I just said “yes”, and did it as favor at first, then started charging money for it later.  Then it kept growing and growing faster and bigger than I could ever imagine.

That’s it. Doubt never entered the picture. I was just responding to a need.

I still think this is the ideal way to make a business. Look for a real need – not an imagined need. Something that people want now, are asking you to do now, and are happy to pay for now.  Respond to that need, and you’ve got a business!

Jonathan Mead, Illuminated Mind, Trailblazer

Quick intro: Jonathan helps people who want to opt-out of the conventional path of having a 9-5 job live and work on their own terms – i.e. the idea that you can throw out the 4-Hour Workweek principle because you’re always doing work that gets you excited. If you want to get an idea of what he’s about, check out the free monthly webinars he offers about blazing your own trail.

Every time I release anything I inevitably face fear. Every product, every launch, every event – there’s always fear and anxiety present.

But whenever I feel that fear I release it. I know that I am doing something important, something that makes me uncomfortable. And that’s very comforting to me. It helps me remember that I’d rather fail than not follow my calling.

Lori Deschene, Tiny Buddha

Quick intro: Lori is the creator behind the insanely popular Tiny Buddha, which shares inspiring stories and simple wisdom to improve your daily life. As a fan of integrating eastern mindfulness practices into western psychiatry, I really admire how she distills eastern principles and shows people how to practically apply them making everyday life more joyful.

I faced doubt immediately after I launched tinybuddha.com.

Prior to starting the site, I tweeted a daily anonymous quote on the @tinybuddha Twitter page–and nothing more. Followers were accustomed to that, and many were unhappy when I started posting links to a website, especially since I was writing anonymously and not really connecting with readers.

I had over 50,000 Twitter followers then, and I put a lot of pressure on myself to create a space that would be helpful to the majority of them. One day, in response to my doubt, a friend suggested to me that maybe I should keep Tiny Buddha in the twittersphere. I realized then that my heart was too far in it to back out. I could either focus on everything I thought I was doing wrong, or learn from it all to start doing things that felt right.

I chose the latter, and though I still feel doubt and insecurity at times, I know one thing for certain: I love Tiny Buddha way too much to ever give up on it.

Therese Schwenkler, The Unlost

Quick intro: I identify a lot with Therese. We’re about the same age, and she used to be an accountant (just about as straight-laced a career as medicine). Unlike me, though, she had the balls to quit her job and start traveling around the country with no specific plan. She’s currently working on her first product, due to launch in September.

To tell the truth, I’m not sure there’s been a single day that I *haven’t* faced doubt. I don’t know that it’s something you ever “overcome;” rather, it’s something that you look straight in the eye every single day of your life, and you choose to embrace it rather than run from it. Where does the courage to embrace doubt come from? It comes from the knowing that Faith is both larger and realer.

I’m still in the process of building my business, but WHEN (not if) it becomes profitable, I don’t expect the doubt to go buh-bye. The more I have welcomed it and allowed it to be as it is, the quieter the voice of doubt has become.

Caleb Wojcik, Pocket Changed

Quick intro: Caleb writes about personal finance and finding work you love at Pocket Changed, and is part of the Think Traffic team with Corbett Barr. If you freelance or have a small business check out his free Get Paid Manifesto, which shows you how to get more money by getting more clients.

I have faced both internal and external doubts in my personal business and my wife’s photography business. Both of our businesses competed in separate “business plan competitions” and neither of them placed. Despite the short-term setback and disappointment we both persevered and have built them into our full-time careers. We also have struggled internally with big decisions about whether to keep going on the same path or to pivot in a different direction.

By spending time thinking and planning we continue to stay motivated towards reaching our biggest goals both financially and personally. We surround ourselves with people that do passionate, unconventional work and that continually encourage us to do the same. Our network of friends and family our key in supporting our decisions and breaking through the doubt of accomplishing our goals.

Benny Lewis, Fluent in 3 Months

Quick intro: When he was 21, Benny spoke exactly one language – English. He now speaks 8 and is working 3 others (check out this video of him speaking all 8 languages). He’s translated (no pun intended!) his rapid language learning skills into a Language Hacking Guide that teaches others the principles behind becoming a rapid polyglot.

I’ve never really considered my earning-from-the-blog to be a business, but one major setback I had while I was initially trying to grow the blog (still a while before earning from it), was that I ran into financial problems and had to put my language learning mission and blogging on hold for most of a month, while I worked double time as a translator.

This could have put the potential growth of my blog in jeopardy, but rather than try and hide it and put on a brave face, I was straight with people and told them in a dedicated post why I couldn’t continue the current project (Czech), and why I haven’t updated much lately. They were very understanding, and even more pleased when I dived back into the project a month later after getting on top of things!

Always be straight with your readers and let them see the human side of you. Sharing my failures on the blog has been a great idea every time (as long as there are plenty of successes too!) because people appreciate that you are human like them and will feel that little bit closer because of it!

Tess Marshall, The Bold Life

Quick intro: Tess has a background in counseling psychology and now teaches people how to be more bold, courageous and brave in their everyday lives at The Bold Life. Her new course, Take your fear and shove it, offers simple, daily strategies for learning to be less afraid so you can take important actions to improve your life.

Two years ago I began getting requests from other bloggers requesting help. They asked me if I would mention their blog, become an affiliate for their product, or do a review or interview of their ebook. I was eager to help and did just that.

When I launched my eCourse in January, I asked several of the same people to help me promote it. Some of them did but others said “no” and others didn’t bother replying at all. I was shocked and angry. I am human.

On another level, I’m wise enough to know not to have expectations, not to give with strings attached, and not to take rejection personally. I also know that what goes around comes around and not necessarily from the same people.

I took the high road, worked through my feelings and the relationship issues and got over myself. Six months later a friend called me and poured his heart about how shocked he was to not get help from the very people that he helped. I told him it was the same with me and it made him feel so much better just to know that. We ended up laughing about the entire situation and ourselves.

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Thank you to all of the above people who shared their stories for this article! And to my readers – I hope you enjoyed hearing about their experiences as much as I did.

If there’s one thing I’ve learned from struggling through the first two years of residency and coming out strong on the other side, it’s that doubt is the natural consequence of challenging yourself, and that doubt doesn’t mean you’re on the wrong path or should give up.

Thank you everyone for coming to visit on my launch day and I would love to hear your thoughts and experiences with dealing with doubt in the comments. What doubts are you facing currently and how are you working through them?

Oh, and welcome to Zen Psychiatry!