Entrepreneurial Angst: Some Things to Consider When Self-Doubt Threatens Your Cool


I jotted down some thoughts after the a recent meeting of my guided mastermind group. Many of what follows could well be advice given to anyone just starting out in anything. But mostly it’s for creators, business-makers, solo-preneurs and spirit workers, who tend to work alone, on a vision unique to them, with a dedication that is driven by love, constantly attended by self-doubt and uncertainty.

Some of this stuff, you just can’t Google.

To my inspiring tribe, I offer this:

Consider that if you can’t see your own strengths it’s because they’re so you that they’re invisible to you. You can’t see your own face either. That doesn’t mean it’s not there.

Consider that it’s a milestone to be celebrated when a teacher or guru says or produces something that you disagree with. You’re growing beyond them into your own person. Pretty soon you’ll have to name what you do.

Consider that when you’re doing things you’ve never done before you’ll feel uncertain. Don’t confuse this with failure. You’re a creator. You’re doing things you’ve never done before probably most of the time. If your default is to feel less-than when in new territory, you’re probably suffering needlessly.

Consider that you might be feeling unequal to your challenges because you’re tired and overworked. When in doubt, floss and lie down. I haven’t done the research, but I know how powerful it is to not do those things, so I’m figuring the same is true in reverse. This is an entrepreneurial thought. If it doesn’t pan out, I’ll toss it tomorrow without looking back. But I have to follow my gut on this one. If you’re like me, you’ll understand.

Consider that when you fail to meet a self-imposed deadline and you’re beating yourself up about it, you’ve slowly and imperceptibly made the transition from having someone else decide your priorities to making your own. Congratulations! You’ve energetically completed your graduation from grammar school and employment. Having failed to meet that deadline means you either set your sites too high or didn’t say no to enough other things to reach your target. Which means you have more self-management skills to learn. But that’s okay. You know how to learn. You do it all the time.

Consider that when you follow hunches and to-do’s that nag at you and they don’t pan out, you might have needed to pass through them, a lot of them,  to get to something brilliant.

Consider that many business milestones may feel at first like failures. What they really mean is that you’re honing that invaluable, irreplaceable asset, your gut instincts:

  • Turning away a client because you know they’re not right for your business, and your business isn’t right for them.
  • Re-doing your entire website because you realize something key is missing or needs to be removed, or because you’ve had an a-ha about what it is you really do.
  • Refusing to barter, because you don’t want what the other party is offering, even though they might be a good connection to paying business.
  • Agreeing to barter with a customer who could really benefit from what you do, whom you really want to work with, and although you keep checking in with yourself expecting to feel as if you’ve sold yourself short, you continue to feel really good about it.

Consider, just consider, that you do have something to say. That doesn’t mean new ideas that have never been thought or expressed. It means telling what the world looks like to you and why it delights, fascinates and horrifies you. Some of these points of view will stay with you forever, and some will disappear one day and never be thought of again. It’s okay to express them anyway. You never know when your expression will help someone else to wake up to their own life.

Consider one last thing: That ugly word, “marketing” means that the only difference between you and your potential clients is that you know what you do better than they do. When you see a need out there in one of your communities, figure out a way to let them know about what you do and how you can help.  Does that feel doable?

This way of life is not for the faint of heart. It’s a life of constant learning, myth-busting, skills development and relationship whispering. Somewhere between all that are rays of light, wings and halos. Yep, you guessed it, that part comes when you’re sleeping.


Okay, that’s it for me this week. Let me know in the comments what I missed, what you’re wrestling with, and what’s helping.

Interested in joining my next guided mastermind group? It starts in October, 2016. Click here for more details, or feel free to contact me with any questions. This is a local group that meets monthly in Sidney, Maine, USA.

Till next time,


by Phyllis Capanna © 2016 joyreport

All content is the sole property of Phyllis Capanna. If you are reading this content on another site, it has been reposted without the author’s permission and is in violation of the DMCA.  © 2016 Phyllis Capanna

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