How to deal with deep-set doubt as a creative entrepreneur

If you frequently have thoughts of despair and lingering feelings of doubt about your ability to succeed as a creative entrepreneur … just sit with them. Here’s how.

This isn't working. That's the single penetrating thought that loves to take up camp in the back of my mind at whim. It especially loves to arrive at the break of day.

As a morning person, I’m often up before the chirping birds and the rising sun. And nothing is more defeating than starting a beautiful day with paralyzing feelings of fear and uncertainty.

In my entire life — and this is no exaggeration — I have never harbored the kind of doubt that I do as an entrepreneur. And the doubt is not unfounded, because the risks of starting a business are indeed high and the probability of succeeding low. So trying to psych myself out and ignoring this reality doesn't work.

Does this sound anything like you? You decided to invest in yourself and your ideas. You’ve dedicated your life to creative service. You’re committed but the stakes are high, you aren’t seeing the fruit of your labor and you don’t know what to do.

Well, I’m not one of those personal growth gurus who absolutely guarantees you will see success, because I don't know your situation nor can I predict your future. I also won’t tell you that thoughts of doubt will go away if you do achieve success, because they don’t (they actually grow as you get more successful).

So my solution (which may be unpopular but is probably more than the more trendy advice on this topic) is to learn to sit with your doubt. And in this article I will pose a series of questions that will help you coexist with the inevitable deep-set doubt that every creative entrepreneur experiences.

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What is your absolute truth?

What is one thing that you are confident in your ability to hold fast to, no matter what? Mine is: I will never ever go back to work in an office again. You may be thinking, never say never, but I feel such an aversion to everything that an “office job” represents that it is my truth.

As a free spirit, a 9-to-5 feels like a soul-crushing assault on the core principles I live by. I value freedom and can’t ever accept that as a backup plan. So no matter the doubts that arise, I’m not compelled to quit.

Because quitting means going back to an office job and I will fight hard to avoid that at all costs. Short of acting unethically, I’d do just about anything not to subject myself to that way of living and working again.

Now this is just me. You may have an entirely different outlook on office jobs. The point is that you need something that you are just as equally passionate about to stay motivated to start and run an abundant business.

You need an absolute that allows you to face that doubt with resolve. Not a positive affirmation that you half-heartedly believe in, but a declaration that quiets the negative rumination (because your unconscious knows you are not playing games).

You need an absolute that allows you to face that doubt with resolve.

So take a moment right now and write your absolute — that one big thing that fuels your drive as an entrepreneur. Your absolute will stir up passion, and passion begets resilience.

Because you need a healthy dose of resilience to keep moving when everyone and everything around you (including your own thoughts) are telling you to stop.

What can you do, just for today?

As a business strategist, I’m often thinking one month out, one year out, five years out. But in the depths of doubt worrying about timelines do nothing but evoke more feelings of despair. You can’t control what tomorrow will bring, but you can control right now. So let’s narrow the scope to a more manageable period of time: today.

I have clients who are in the energy coaching field which I find to be a fascinating method of alternative healing. To understand their business, I’ve had to learn more about Reiki and want to share its principles:

Just for today, I will not worry

Just for today, I will not be angry

Just for today, I will be grateful

Just for today, I will do my work honestly

Just for today, I will be kind to every living thing

What stands out to me is just for today. You can do it, just for today. You can be that, just for today. Just for today, you can stop fretting about the destination and enjoy the journey. Just for today you can do your work with intention and conviction. Just for today, you can put 110% into starting or running your business.

Just for today you can do your work with intention and conviction. Just for today, you can put 110% into starting or running your business.

I’m not the person I thought I would be five years ago. My life has unfolded in ways I’ve never imagined. And even with a strategic mind, I know better than to try and predict exactly what life will be five years from now.

Likewise, I’ve survived several years as a business owner despite so many false starts, misdirections and setbacks. So that nagging voice has no basis for what can’t or won’t happen. If I had heeded its advice then I would not be here now. If I believed the doubt I never would have designed an abundant life and business. 

This too is the mindset you must have. Doubt is rooted in assumptions about the future. And unless you are a prophet you aren't qualified to foresee what is to come. So just for today, stay present and concern yourself with today’s work. Then tomorrow, repeat if you can.

By what standard are you judging yourself?

Take a moment and reflect on the internal dialogue that accompanies your doubt. My assumption is that you replay a script that is chock full of one-liners such as:

  • This isn't working (my favorite)
  • I’m terrible at this
  • I don’t know what to do
  • This is so hard
  • I’m stuck
  • I’m confused
  • I’m never going to make this happen
  • This isn't going anywhere
  • I should have never started this

The next time you are caught in this loop, with these thoughts floating round and round your head, I invite you to interject with a question: why do I think that?

  • Why do I think this isn’t working?
  • Why do I think I’m terrible at this?
  • Why do I think this isn't going anywhere?

Another way you can ask it is: how do I know?

  • How do I know this isn’t working?
  • How do I know I’m terrible at this?
  • How do I know this isn't going anywhere?

When you reframe your one-liners from declarations to interrogative self-inquiry, it’ll gently interrupt that cynical cycle and help reveal where these thoughts are coming from.

Because it is likely that you are unconsciously comparing yourself, your work and your business to some standard of success you’ve adopted from someone else — and the doubt kicks in when you’ve determined that you fall short of someone else’s standard.

It is likely that you are unconsciously comparing yourself, your work and your business to some standard of success you’ve adopted from someone else.

Shifting statements to questions will help you uncover this standard and once you do the next question should be: should that be my standard?

What is going well?

Finally, when curled up in the corner somewhere sulking because things have not materialized the way you wished they would, pull out my secret weapon.

Think on good things, such as:

  • Something that went well in the last month
  • Something that excites you about your work
  • Something that catapulted you forward
  • Some small or big win you recently had

I’m confident that you can identify just one thing that has gone well. That one good thing is your life line because it shifts your mentality from grim to gratitude. This elevated state of thankfulness will inspire you and inspiration will motivate you to create.

This elevated state of thankfulness will inspire you and inspiration will motivate you to create.

If you can find yourself back to your creative flow you are in a better position to find solutions to your problems and to see a way forward when previously the path seemed blocked. Your creative flow is the place where you feel present, confident and optimistic.

So when in doubt, dwell on the good. The more good you think of, the more good you will feel energized to bring about — and more apt to slip into your creative flow which is where you perform at your best. This is the phase you need to be in in order to create an abundant life and business

If you need help dealing with doubt so you can reach a more optimal state of performance and push forward in your business, I invite you to take the first step and set up a complimentary strategy session.

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