Randomness and the Benefits of Freelancing

Freelancing is risky business. From client to client. Feast or famine. Lost bids. Steep competition.

Those are a given. You know what you’ve gotten yourself into. Everything might stop tomorrow, you know that. You can fall on your feet if things go bad.

Since you’re in this already, how about adding more randomness? Because freelancing benefits from randomness, and freelancing gives you the benefits of randomness.

Antifragility: Before You Can Benefit from Randomness

In his book titled Antifragility, Nassim Nicholas Taleb introduces the idea of the bi-modal strategy to taking risk.

Take all the risk you want, but be here tomorrow.

Instead of seeing all risks the same way, he recommends living a life that is set up to deal with two kinds of risks at the same time (bi-modal).

  1. Identify risks that might lead you to ruin, and make sure you’re set up to be protected from those. Risks with high downside potential, avoid messing with those. Risks where you might lose your whole life savings (e.g. partnerships that go bad), risks where you might die, risks where you might get sick and you can’t work for months, risks where you would lose your reputation. Remove your fragilities.
  2. And then, make small bets with risks that won’t cost you much if things go bad, but where you risk getting big rewards.

Avoid all the risks in between those two poles.

As a freelancer, you want to position your practice to benefit from such bi-modal risk strategy.

1. Ways to Avoid Risks of Ruin, as a Freelancer

You can find the wisdom of avoiding risks of ruin is some of these popular statements:

Charlie Munger is often quoted that “it’s better to avoid stupidity than seeking brilliance”. You get more benefits, over the long run, to simply avoid the worst, than to seek the highs of the best. The worst thing you can do with a client is to be insulting, to make them feel like fools. So do the opposite of that, always: be mindful to make your clients feel honored when working with you.

His partner, the famous Warren Buffet, stresses this rule: “you can never have enough reputation”. You can build a reputation over a lifetime, and lose it in a minute. Your reputation is fragile, and without a good reputation, you don’t have a freelance business. Keep your word. Honor your commitments. Prevent being at fault.

Jason Fried of Basecamp often recalls this lesson he got from his father: “No one ever went broke making a profit”. Reduce your costs, live within your means.

Here’s a have-done list implementing that groundwork:


Before I can say I’ll have reduced my fragilities as a freelancer: Made sure I made a profit Reduced my costs Ensured a revenue Made sure I protected my reputation Made sure I honored my clients Respected my commitments

Week to week, those will take you further than risking their opposites.

But what’s interesting here is what’s missing: strategies that are closer to the middle. Nothing about sticking with a particular kind of client. Nothing about diversifying your types of client. Maybe those are good, but maybe those are strategies that are about “playing in the middle”, the opposite to the bi-modal strategy.

So let’s jump to the other end of that spectrum. Let’s take risks with known costs, but high potential rewards.

2. Ways to Add Randomness with Small Costs but Big Rewards, as a Freelancer

As a freelancer, you’re set up with more freedom to move around, allocate your time differently, work from anywhere, make small bets without asking for permission.

You’ve got room to add more randomness:

  • Block a half-day to learn something or to master a skill. You know the cost of losing a half-day’s work. But that half-day might add a lot to your ability to drive value for your clients. A skill that’s mastered is worth more than a skill half-mastered. That includes meta skills like learning to sell (helping the client make progress).
  • Show your work publicly. The known cost to you: you’ve spent time publishing an example, a demo, a draft, a short video. The benefits: you might attract a new client.
  • Hang out in new communities. The known cost to you: you’re investing some time to listen attentively or answer some questions. The benefits: you might get new ideas for an article. You might leave a trail back to your site via a link back to an article you wrote.
  • Publish a constellation of mini-struggle solvers. Create an online collection of things you publish where each item is a do-it-yourself answer to a problem. The known cost to you: developing a habit of publishing on a frequent basis. The possible benefits: a trail of links leading back to you, working for you over time like compound interest.
  • Have hobbies, invest in silly interests. The known cost to you: a few bucks spent on buying silly objects you can later re-sell. The potential benefits: you might learn of a new business segment, find new friends, find potential clients showing struggle you can solve, have stories you can tell in your articles to make you more interesting, find new parallels to your work in another discipline so you can get inspired. You might grow empathy, through your own purchase or through selling it again, for what causes someone to buy something.
  • Do scary-important things. Popularized by Seth Godin (in Linchpin) and originally by Stephen Pressfield (in The War of Art), the concept of The Resistance is what happens when you do something creative and you start avoiding the work, being scared of the result. Learn to recognize The Resistance as a sign that you need to push through, because you’re doing something that might matter to you. The known cost to you: you invest time to parse and re-write your thoughts. The potential benefits: you’ll be publishing something of a quality that most other people can’t attain, making your work remark-worthy.
  • Develop a point of view. The known cost to you: trudging through the discomfort of being different, losing a few followers. The potential upside: seeing a part of the world most people can’t see, seeing opportunities others don’t, seeing threats others don’t, be able to survive while others perish, attract a new following.
  • Discourage your clients from hiring you. The known cost to you: you risk losing a client (because you respectfully encourage them to go with their other, less costly options). The potential benefit: you attract some of the greatest, most intentional and clear-headed clients, or more importantly, you get to discover the deep value you can deliver on with your proposal.
  • Pick a fight with bigger foes. The known cost to you: you risk being badgered around publicly. The potential benefit: you make your reputation antifragile, not just robust, where your reputation benefits from being tested. You might attract more attention, find a fragility in the market, or make some new allies. (But don’t pick a fight with smaller foes, that’s called bullying.)

You’re not doing all those things while counting on the benefits to materialize. You’re investing a bit of your surplus so that you might reap some random, surprising benefits.

The Fragilities of Avoiding Freelancing

All of those point to some obvious benefits of going freelance. If you’re at a point where you’ve got enough integrity, self-displine and a clear enough mind to both avoid the risks of ruin and benefit from randomness, you might wonder why you shouldn’t try freelancing.

Keeping a job might sound more robust, but it has hidden fragilities. You might lose that job. You might have built a fragile reputation. The industry you’re in might collapse. You might be depending on skills that are transferable nowhere else.

Betting everything on building a product might sound courageous and noble, but it has hidden fragilities too. You might be forced to wed yourself to investors. You might poison your close relationships. You might be forced to alienate your first customers for the sake of profitability.

So consider doubling-down on the randomness of freelancing. It might seem risky, but it might take you to new, random, places.

Stay sharp!


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