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Antifragile freelancing: Business resilience in uncertain times

A Future Is Freelance podcast

I remember a couple of years ago, someone I am related to asking if I was “still” freelancing? This was accompanied by a raised eyebrow, clearly suggesting something was amiss in my overall lifeplan. Antifragile freelancing as a strategy was not in their lexicon. Surely, in their mind, self-employment had been a polite euphemism for between jobs/will do anything to keep the lights on, while seeking full-time employment?


That was never my plan, and still isn’t. And I am more glad about that than ever, as we seem to face uncertainties never seen before – from climate to the economy to geopolitics, everything seems less predictable than at any time I can recall, and I am so relieved to be freelancing right now.

Of course being a business-of-one has inherent vulnerabilities, because if anything happens to you and your ability to deliver your work, then you’re in big trouble. But, I still argue that freelancing is antifragile and strong, as a strategy. You can invest in your long-term professional resilience in lots of different ways, from building social capital with your clients to diversifying your activities. And as I describe in the episode, there have been times when I found out exactly which of my clients had my back in a crisis, as well as how I could pay it forward when they had their own issues.

At the moment though I would hate to be responsible for anybody else’s income/mortgage in addition to my own, and that’s definitely one reason why I have no intention of ever growing my business with employees – been there, done that, and relieved to be out of it right now.

Anytime I feel delusions of growth coming over me, I quickly re-read/re-listen to Paul Jarvis’ superb book Company of One: Why Staying Small is the Next Big Thing for Business, and snap myself out of it, remembering why I love being an unapologetic solo operator. Of course I collaborate regularly with others, but on an associate/supplier basis of professional service – when I need a specific expertise, there will always be a great freelancer who can provide exactly what I need.

Why is freelancing antifragile and strong?

For me, there are so many advantages to solopreneurship, but the most critical upsides in uncertain times include:

  • Diversified income – with eggs in many baskets, no one can fire me from 100% of my job at any time
  • Practice at hustle – unlike many employees, I am continually developing my business and ready for the next opportunity
  • Agility – when I need to pivot I can do so fast. I don’t need anyone’s approval or consent

This has been brought home to me hard lately by seeing the slew of redundancies in my network, especially in spheres like collaboration tech and web3. I am seeing some incredibly talented people, who 6 months ago were being headhunted and fought for, being unceremoniously scrapped by employers who are suddenly in trouble.

I want to help if I can, and if anyone reading this has been affected then please let me know.

If we’ve worked together, could I write you a reference? Doesn’t matter if I was the supplier and you the client, I can still write about what you were like to work with, and speak to the qualities you want to highlight.

Check out my network as well, and if there’s someone you would like me to connect you to, then shout. Better a warm intro, than a cold inmail tossed into the ether, right?

Whatever you are looking for in terms of a next move, I will never have a job to offer you (see above.) But, sometimes the most helpful thing might be to talk and bounce ideas/advice around with somebody else, and I am totally here for that.

And I won’t even try to sell you on freelancing, if a job is what you really want – though I will try to encourage you to develop a resilient and ready-for-anything employee-preneur mindset and profile, to help ride out whatever lies ahead.

These are strange times, so we need to support each other

Maya Middlemiss

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