The Best Freelance Advice You Never Hear

Growing up, Spanx founder Sara Blakely had to answer an unusual question at the dinner table. It points at a type of learning that many freelancers and consultants avoid because it’s uncomfortable.

Yet, that very discomfort offers the key to eventual breakthrough.

Here’s the way Blakely tells the story in Gillian Zoe Segal’s book Getting There:

When my brother and I were growing up, my father would encourage us to fail. We'd sit around the dinner table and he'd ask, "What did you guys fail at this week?" If we had nothing to tell him, he'd be disappointed. The logic seems counterintuitive, but it worked beautifully.

He knew that many people become paralyzed by the fear of failure. They're constantly afraid of what others will think if they don't do a great job and, as a result, take no risks. My father wanted us to try everything and feel free to push the envelope. His attitude taught me to define failure as not trying something I want to do instead of not achieving the right outcome.

Let me start by pointing out the obvious: failure is uncomfortable and embarrassing. It can cause emotional, relationship, and financial pain.

Kids don’t seem to mind it as much. When you drop a girl who has never skied on the slopes, she expects to fall down. Assuming she hasn’t hurt herself, she can fall down again and again and laugh. The failure can be almost… fun.

Certainly there’s no stigma attached to failing at something she’s got no experience with.

There’s no expectation of mastery (yet) or the praise and accolades that might come from an impressive performance.

She may see other kids zipping down the slopes or zigzagging around moguls, compare her own efforts, and feel a tinge of disappointment or envy.

But for the most part, she’ll submit to the process of learning through trial and error. Fall. Get up. Try again. Try something new.

What is so interesting about Blakely’s experience is her father’s deliberate, near-nightly effort to celebrate trying new things, no matter the results.

Many of us grow up in families that do the opposite, and this isn’t all bad. For example, I was capable of making all As in school, and if I didn’t make all As, my parents rightly took the odd B or C as a sign that something was amiss.

Did I not prepare for a test?

Did I not turn in my homework?

Did the teacher make a mistake?

My parents wanted me to be a faithful steward of my God-given abilities, and they had the foresight to see how excellent grades in high school could lead to scholarship dollars down the road.

Did they care about my grades more than my physical health, emotional well-being, friendships, or various other interests? Of course not.

Even so, kids remember the emotional shape of conversations—how they felt—more than the content—exactly what was said. They have thoughts and form impressions, some more true and accurate than others. Like magpies building nests from gum wrappers and string, they build belief.

So I pieced together the belief that failure is bad.

When my parents anticipated that some interest of mine might end in failure or disappointment, they would highlight the risks and try to dissuade me: “Don’t get your hopes up.”

If I were to ask them now about some of their choices or points of emphasis, they’d most likely shrug and say, “We thought that was our job as parents. Parents don’t enjoy seeing their kids be disappointed. We couldn’t help but feel some of what you felt.”

To be clear, I had and have exceptional parents, and my point here isn’t that they made some egregious mistake but that 1) the way Sara Blakely’s father welcomed failure was highly unusual, and 2) kids grow in the direction of praise.

Kids and adolescents must go through a series of trials. We must make the errors. That’s what childhood is, in a way: Discovering what you’re naturally good at (and not), and then deciding whether to put in the practice (or not), to get better.

What’s so remarkable about Sara Blakely’s story is that her father found ways to reward that trial and error process through his children’s adolescence and young adulthood.

He advised them to stay in school, only a different kind of school. Failure tends to be a better teacher than success because often, on the other side of success, we find it difficult to deduce why we succeeded.

One year, when I played Little League baseball, the leagues across the city of Nashville organized a fundraiser. All the players could sell World’s Best chocolate bars—an egregious misnomer for barely edible brown wax.

The prize for the kids who sold the most? Standing out on the field with our minor league baseball team, the Nashville Sounds, during the National Anthem.

For whatever reason, that prize captivated me, so I sold a crap-ton of chocolate and got to stand with the third baseman.

Any number of factors may have contributed to my success:

• Was I better at sales than most kids?
• Was I more determined to win the prize?
• Did I happen to pick a winning sales strategy?
• Did my parents’ friends have more money than most?
• Were people we went to church with more likely to give to a kid with a cause?

I could have done the exact same thing the next month or next year and gotten different results.

Failures are better teachers because, though positive results can be difficult to trace back to a single factor, we can usually find some causal link in a failure, something within our control, and pinpoint what we’ll try differently next time.

Determination is worth bringing up because all of this talk about analyzing failures, identifying factors, and getting better results assumes that we keep trying.

Kids who wipe out on ski slopes must gather their gear and try again.

Adults often praise kids for their resilience in the face of failure, and the “keep trying” enjoinder strikes me as only slightly less valuable than “find something new to try.”

Creative entrepreneurship brings so many challenges, and thus so many opportunities for “failure.”

I’d really like to see more freelancers and consultants define failure the way Blakely’s father did: not trying something you want to do.

The “right” results may come only in time—or never—but not trying causes regret. We laugh at failures more easily than we rid ourselves of regret.

I wonder what type of joy we’d see in our businesses and lives if we truly embraced a “no regrets” mantra. (I’m writing for myself now, too.)

Here are several questions for both of us:

1. What’s in your heart? What is it you want?
2. What is it you aren’t trying because you’re afraid to embarrass yourself?

What has been in my heart is writing stories. Many stories have lit me up with beauty, joy, and wonder. I want to write a story that does that for someone else. I want to create characters people feel like they could pinch and build a world so vivid and palpable people are sad when they have to leave it.

I want to make beautiful things.

And what if I try and the story isn’t compelling? What if it sucks? What if I give it my best effort and people think it’s embarrassing? Worse, what if I give it my best effort and no one cares?

But wouldn’t never trying and letting that fire inside me die with me be sadder than people’s indifference?

And don’t I want to set an example for my children—perhaps even for you—of a fallible and rather sentimental and silly man trying to shoulder through fears to make a real, ringing, sweet connection with other people?

Yes, I think so.

So, I’m writing fiction again. Slowly, painfully, clumsily. I doubt it’s very good—though my wife likes it; ha!—but what matters is that I’m trying something I want to do.

Now, let’s apply this to your business.

What do you want for your freelance or consulting business?

What are you not trying because you’re afraid it won’t go the way you imagined?

I hope you’ll start trying. Be the girl whose overcautious parents dressed her like a pink marshmallow and get down to the real work of half-gliding, half-tumbling down the slope. She’s having the time of her life.

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.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. Custom Business Roadmap. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign. Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.