nerd hides under the table

How do freelancers deal with uncertainty?

Dealing with uncertainty is a fact of life for anyone who has a solo career, whether they describe themselves as a freelancer, entrepreneur or whatever.  Despite all the wonderful reasons why you should be your own boss, that feeling that it can’t last, or that you can’t plan ahead never goes away.

But you can deal with it, embrace it and learn to love the way it spurs you on every day.

The thing is to remember why you work, or want to work for yourself. There are no set answers. There are infinite ways to create something new. And just when you think you’ve ‘got’ it in your grasp, it all changes again.

The most difficult part of working for yourself is that you feel you need to understand everything before you begin.  To have all your ducks in a row.  But the nature of being different, of being entrepreneurial, is that there are sometimes no answers.  You’re going to create them.

Uncertainty is a sign of humility, and humility is just the ability or the willingness to learn. (Charlie Sheen)

I learned this lesson on a short business trip to San Francisco back when I was a government employee. I was lucky enough to share the trip with a group of young tech start up entrepreneurs from the UK who got me thinking very differently by their approach. They seemed to thrive on not having a roadmap for their big ideas, but a series of routes that they could take, learning as they found better, quicker ways to make things happen.

Don’t get me wrong. Not knowing what’s coming over the horizon is terrifying. Particularly when others rely on you, or you have bills to pay. So, how do you deal with it?

1.     Stop trying to control outcomes, look at the possibilities.

I recently asked a friend what she was planning next.  She told me she didn’t do plans, because she found them restrictive. For most of us, planning helps us feel like we are in control, but in doing so we are already limiting ourselves.

Stop checking all the information around you to try and analyse what to do next and go with your gut instinct. Think about all the times in your life you wished you had done that, because the continual checking doesn’t move you forward.

2.     What’s the worst that can happen?

Ask yourself, ‘What’s the worst that can happen?’ Most of the time, the answer is a lot less scary than the scenarios that are buzzing around in your head when you are stressing about them at 3am not being able to sleep. Are you being realistic? Who knows? But then if we spent our lives avoiding doing anything because of a fear of the unknown, life could be very dull indeed.

3.     Spread your bets.

You may be utterly convinced of your dream business idea, or looking at a radical change in the way you run your life, but rather than trying to make the one right guess on the outcome, try and give yourself a range of options so that you’ve got room for manoeuvre.

4.     Stay agile

If you’re an experienced freelancer you will know the value of the network and keeping your ears to the ground.  There’s no substitute for detecting opportunities as soon as they happen. Focus on how you can act quickly and decisively to take advantage of these as they arise.  Don’t get locked into contracts that might seem financially valuable in the short term, but mean you have to turn down better opportunities later.

5.     Use your inner wisdom

Hey, we all make mistakes. We’ve all seem other people succeed. As we journey through life and experience new situations, we take lessons from our mistakes and hopefully learn not repeat them over and over. Think about how children learn to deal with life. They aren’t born with the route map, and they learn what to do and what not to do as they grow up. As we grow in experience, the less daunting periods of uncertainty should be. And you can apply what you’ve already learned to each new situation.

6.  Rely on your networks

There is a big role for your friends, colleagues and confidants here.  They can help you reduce the uncertainty by surrounding you in love, belief and trust. They believe in you, and they want you to succeed. That doesn’t mean that they will validate all your ideas as world changers, but that they will give you honest, rounded advice and ideas that help you shape your future.  Think of it like this, you are as experienced as all the people in your network and if you can draw on that, you’re pretty much prepared for everything.

As for the uncertainty, accept the fact that it will never go away and that you will continue to have some sleepless nights.  But it’s what drives you on to keep being curious about the possibilities. I’m sure you wouldn’t have it any other way.



Who is Alex Butler

Hello, I'm Alex Butler and I founded the KindredHQ community and blog back in 2011 after I re-started a freelance career. I LOVE freelancing and I wouldn't swop the freedom, control and joy of working for myself for anything. But I realised how much I missed the company and energy of other people - of having a team around me. So, I got a few people together one day with our laptops, a jar of coffee and some jelly babies and we sat and worked together one afternoon. We've been doing that every week in London, UK since then! I am still 100% freelance and I like to share the everyday highs and lows of being a freelancer here on the blog.


  1. Kathryn Hall Reply →

    Great post. I think coping with uncertainty is one of the hardest challenges when you first go freelance but it kind of goes with the territory. I always find thinking sensibly about the worst case scenario helps.

  2. Joann Reply →

    thanks for this post! I jumped into the freelance bandwagon and weird it may sound but it’s that uncertainty that keeps me going 🙂 A friend once asked if I’m not afraid, I told her that I am but I have the choice – to surrender myself to that fear or focus instead on opportunities and possibilities.

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