8 Inspiring Life Lessons from Sketch Guy’s Approach to Entrepreneurship

Estimated reading time: 3 minute(s)

New York Times’ Sketch Guy—aka Carl Richards—addressed the COCAbiz audience yesterday in a talk addressing not just his famous Sharpie-and-cardboard sketches but his approach to entrepreneurship as the intersection of business and art. 

Sketch Guy—aka Carl Richards
Carl Richards’ take on Entrepreneurship

As both an artist and the director of investor education for Buckingham Asset Management, he spends a lot of his own time in that gray area, and his weekly column for the Times explores it by taking the financial planning principles learned in his day job and breaking them down to their simplest form (and most digestible for the finance-averse): napkin sketches.

Here are eight life gems we gleaned from his talk—check out his latest book, “The One-Page Financial Plan,” for more money-related wisdom.

1. Listen to your Thing. What is it that keeps you burning—that you would be less yourself without? Is it a passion for sustainability that has nothing to do with your day job? Is it writing essays? Is it, well, sketching? Listen to it and put it into practice. If that’s your Thing, you’re the only one in the world who can do what you can do with it, Richards says, quoting Martha Graham.

Sketch Guy
Carl Richards speaks at COCAbiz

2. Take a kindergartner’s approach to creativity. Richards talked about how a class of kindergartners would raise their hands when he asks who among them is an artist. A few grades later, there were fewer hands—and then in his daughter’s high school art class, there were just three (and those were quickly taken down). What happens to us along the way?

In kindergarten, we’re compelled to share our ideas with the world, maybe through Play-Doh or permanent markers on the living room wall. And that creative expression is great when you’re 5 or 8, but then suddenly, somewhere, it stops being awesome, Richards says. “We’re told by the world, ‘Go back to doing something responsible,’ and you’re told to put that thing in a stainless steel capsule and cram it down as far as you can or do it as a hobby. And that’s all OK, but I feel like there’s also an opportunity for us to dance with this thing.”

3. You are not the judge of your work—you just make it. “It’s not your job, it’s not your business, to determine how good or valuable it is—this is really, really important,” says Richards. “I’m giving you permission to let go of describing whether it’s good or not. Your job is just to create.” Sometimes your best work will fall flat, Richards says, and other times what you consider your worst or most desperate work will be what takes off.  So just start doing: The market will figure it out for you.

4. The plan doesn’t matter: It’s the on-going process of planning and course correction along the way. Richards got into financial planning because he loved the idea of helping people plan out coming decades. “We’d sit down and start asking them questions like, ‘What day are you going to die?’” he says. “You see the problem here? We’re making these assumptions from the very beginning that nobody even knows the answers to.” Financial planning is throwing a dart at three decades from now to pinpoint where you want to be—and there’s no straight line there. The part that matters and gets you to that dart (if it even stays in the same place for 30 years) is how you react and adjust your plans in response to when life budges in along the way.

Sketch Guy

5. Continuing the theme of No. 5, another word for “uncertainty” is “reality.” After all, Richards said, quoting Mike Tyson: “Plans are great until someone punches you in the face.”

6. You don’t have to be right all the time—just try to be a little less wrong. Mistakes, bumps along the way and even failures don’t mean you should give up on your startup or stop writing or otherwise ceasing to do what your Thing is. “We’re going to let go of this need for this false sense of precision, and we’re just going to embrace uncertainty—or in other words, embrace reality. We’re gonna build a plan with some guesses…and then we’re going to take a step and see what happens,” Richard says.

7. The Imposter Syndrome is real. If you’ve ever felt like today’s the day someone’s going to figure out that you’re not qualified enough for your job, that you’re a fraud, or that you don’t deserve an honor, show or publication someone selected you for—well, you’re not alone, Richards says: Seventy-two percent of incoming Stanford MBA students checked a box saying that they were the only mistake the admissions committee made.

Sketch Guy

8. Fear is your friend, but you don’t have to hang out every time it comes around. Fear can save your life and keep you from doing stuff that could kill you—so that’s definitely a good thing (embrace that side of it). But when it comes to startups or creative projects or hitting “send” on a pitch, you can also tell it to go away because it’s not needed right now, Richard says. Just because it’s there doesn’t mean you have to hang out with it—in fact, Richard says, the fact that it showed up in the first place means you’re about to do something cool.