Thoughts on Stupid Ostriches, Rubber Fences, and Winning More

At Craft + Commerce in 2024, one of the speakers, Jen Olmstead, mentioned that she grew up on a 250-acre ostrich ranch in Texas. You read that correctly. Perhaps you’ve never thought much about ostriches, the heaviest and largest birds on earth, so here are three facts to set up a point I want to make about rubber fences:

• They can run up to 43 mph (69 kph) and maintain a speed of 30-37 mph (48-60 kph).
• They can be 10 feet tall and weigh up to 320 lbs (145 kg).
• Their brains are the size of a walnut.

Being big and fast—and with very large eyes, to boot—helps when you’re scanning the vast savannahs of sub-Saharan Africa for threats. But being big, fast, and stupid doesn’t help when you live in Texas, when the threat is a stationary fence, and when you run into it fast enough to accidentally kill yourself.

Olmstead’s father had to install rubber fences to keep from losing $2,000 every time an ostrich self-destructed.

It’s quite an image: a black feathered American football going faster than a ski boat bouncing off a tire.

Now, we can poke fun at stupid ostriches, but most animals struggle when you take them out of their native environment. Strengths become weaknesses. We must make all sorts of accommodations to protect them from themselves.

What are your rubber fences?

You have strengths and propensities that will enable you to thrive in one environment and wreck you in a different one.

We hear all the time that we need to adapt, but we typically think about adaptation in terms of macro-level trends and issues. Adapt to COVID. Adapt to AI. Adapt to more competition in the freelance and consulting market.

One click down, we think about adaptation as situational flexibility. Spend less money when you earn less money. Roll with the punches when your flight gets delayed. Agree to reschedule a call.

Neither the macro or situational is what I’m getting at here. There’s a third type of adaptation which involves putting specific measures into place to help you avoid repeating mistakes.

For years, tax season guaranteed a punch to the gut. I’d hear from a CPA that I hadn’t made big enough quarterly payments (again) and that I still owed some sickening amount of money I didn’t have (again).

Then, I read Michael Michalowicz’s book Profit First and learn a simple solution: Take 20% (or whatever) out of every single deposit and move it to a different account where you won’t see it or be tempted to spend it.

The rubber fence for my blind entrepreneurial optimism was that simple practice. Every year that I took the Profit First approach I got a tax refund.

By asking certain questions, you can pinpoint blind spots, avoidable mistakes, and walnut-brain lapses in judgment:

• Which of your strengths and tendencies can hurt you as soon as help you?
• What are the worst business decisions you’ve made recently?
• What mistakes do you make when you’re at your worst?
• What about your work has been least satisfying?

Notice the patterns. Install rubber fences, some cycle-breaking intervention, some solution that’s obvious in hindsight.

You position yourself to win more if you stop making the same predictable mistakes.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
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