Dealing with doubt as a solo entrepreneur


Doubt is a bugger. It really is.

As a self employed entrepreneur I am 100% sure I am not alone in the common bouts of doubt that crop up and threaten to spoil my flow, my vision, and my mojo.

As my partner will attest, despite loving what I do, and despite knowing I do what I do well, those moments of doubt happen more often that I would like and confidence runs out the back door.

Without the support of colleagues, business partners or associates on hand, re-assurance can be difficult to self talk, letting those inner demons loose with their back chat and negativity.

Am I doing this right? Am I charging enough? (usually, no…) Should I jack it all in?

Our doubts are traitors, and make us lose the good we oft might win,  by fearing to attempt. ― William Shakespeare, Measure for Measure


So, what to do when you can’t see the wood for the trees? How do you cope when it all seems too much, when it feels like it won’t happen, or when it just seems all a bit…well..shit?

1. Get a mentor

Whether a formal arrangement or a mutual buddying system, having a mentor to call on is invaluable. Navigate each other through the rocky patches of doubt, pep talk each other into the rock star confidence you really deserve. Whether online via Skype or in person over a flat white, having a rock to rant at and be re-assured by will go a long way to re-balance you.


2. Ground yourself with people who know and love you

Give your best friends or family a call, and connect with someone who knows you for who you are intrinsically, and who loves you regardless of business success (or failure). Getting back to who you are, what your essence really is, will keep you earthed, in line with your real goals and desires, and, for want of a better word, sane.

One of my favourite people to talk to is my friend Emma, herself an entrepreneur (and very successfully so), and we have also been friends who met through work almost 15 years ago. She knows my skills, she knows my background, my inner demons, the whole lot. Emma sent me an email just yesterday which reminded me how much I rock, and it is staying in my inbox for a while as a reminder.


3. Build  or find a tribe of support

Finding a tribe of people to nurture and support you is so empowering. I am part of Leonie Dawson’s Amazing Business and Life Academy, and regularly call on the women in the masterminds and forums to brainstorm ideas and to connect with. Being part of a tribe like this works both ways, of course – using your unique perspective to nurture and aid others will give you a wonderful feeling that also raises your confidence (and makes you feel like a nicer person).

My Access All Areas group works in the same way – we support each other, inspire each other, celebrate successes and hold hands through bad days or times of negative self talk.


4. Get a coach

Sometimes it really helps to have someone metaphorically running by the side of the river while you row. I had engaged coaches at various stages of my career, and the fact that someone is dedicated to working out your goals, strategies to get you there, and to unpack what’s holding you back makes you feel accountable and gives structure to what can often feel like a vast and blank landscape. Find someone you resonate with, ask for recommendations of coaches, and who you work with depends on the kind of support you need.


5. Step away from it all, baby

That’s right, step away from the screen, go and stretch your legs, look at some art, go for a walk/run/yoga session, unplug from your thoughts and let it all settle. Sometimes being too close to something can drive you  little doollally, so re-gaining perspective is never a bad thing. If that happens to be found at the bottom of an espresso martini? Hell, who am I to judge… (and make sure you invite me!)


6. Ask someone for feedback

I met up with the lovely Liz Fraser this weekend, to bounce through some ideas for her new projects – as she said in her subsequent blog post, sometimes you just need to gather some reactions and feedback from a range of people. Reach out to test the waters by inviting constructive criticism on a project or idea, and garner the results to tweak and adjust. Also, ask existing clients for feedback – we may not always like it, but areas to improve will be easier to identify just by asking the question.

The worst enemy to creativity is self-doubt. ― Sylvia Plath


7. Be aware of how you feel, and how you want to feel

I have a massive girl crush on Danielle La Porte (like, massive), and admire her work greatly. One of her mantras which I kepe coming back to is that goal setting is not about the goals themselves, but about aligning yourself with how you want to fee. Do you want to feel calm, confident, capable, energised? Or do you want to feel frazzled, toxic, burnt out and stressed? Check in with yourself on how you are feeling, and adjust what you are doing to alter that state.

8. Make a record of the good things

Last year I started a jar of awesome. In it, I put little Post It Notes, or scraps of paper with awesome things as they happened. They included earning £500 in one day by not even being at work, being featured on key sites, a magical day in the snow with the Minis, everything from work success to times I felt great, and special moments with family and friends. I dip into it when I feel a little wobbly, and the little snapshots of awesomeness bring me back into how I felt when I wrote it. Suddenly, I am back on track with my rockstar feeling of confidence.

Do you struggle with moments of doubt as a solo entrepreneur? How do you deal with those times?

I would love to hear in the comments below.

Stay rocking, positive and confident, you superstar.

jo gifford


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Jo Gifford

My work is about helping people work in smarter, creative ways + getting their message out to the world via killer content—blogs, copy, images + social. I am a designer, writer, blogger, mentor, author, creativity addict + prolific geek. You could call it a portfolio career of multi-potential multi-passions. I call it being me.
Work with me, Shop with me, and Chat with me!


  • Rosie Slosek

    For me, I grew in confidence to the point when I could recognise that it was an outside influence that was causing it (lack of sleep, excess nervous energy, frustration at something else). Now I say to myself, I am feeling that because I am over-worked/tired/eating bad chocolate, it will pass, ignore it, carry on.

  • Alenka

    Great post! And really useful ideas to get over the overwhelm. I learned to listen to my soul & body and take time off when needed. Or just do something different. That’s why I do my weekly plan, I always try to do the things in that week, but not necessarily in the day I originally planned it (if possible of course). Sometimes I am more into doing, other times I need more dreaming. Having someone to hold you accountable is also very important, better if it’s someone in more “formal” connection (coach).

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