I gave a version of the following presentation to the Entrepreneurship Class at my high school – Oakwood School, in Morgan Hill, California.
Good morning, Oakwood (and anyone who’s ever sat in a classroom wondering what comes next). I’m Drew. In 2010 I was in your exact seat thinking success meant picking the one right path and never messing up.
Spoiler: that’s not how life works. On paper my résumé looks like a straight line—job to job, title to title. In reality? Twists, turns, experiments, surprises, and a bunch of lessons I couldn’t have learned any other way. I wouldn’t trade it.
This post is the talk I wish someone gave me back then: three myths that mess us up, four lessons that actually help, and a simple way to find your next right step—today.
“You don’t need a perfect plan. You need the courage to take the next right step.”
Myth #1: You have to have it all figured out by graduation
In high school I was certain I’d be a therapist. I went to college, stacked 18-credit semesters, worked three jobs, had two kids, and sprinted so I could “start my real life.” Then my wife asked the question that changed everything: “Do you know how much therapists make?”
I didn’t. (Turns out, not enough for the life we wanted to build.) I ugly-cried, mourned a dream I’d had since middle school, and pivoted to law. If you’ve ever switched majors or plans and felt like you “failed,” this is for you: you didn’t fail—you learned.
I chose estate planning because people told me it was meaningful work with a life outside the office (hello, 3 p.m. dance recitals). I loved the planning side, then interned in a trust department where we carried out plans after someone passed away. It was good work, but something was missing: the deep, human conversations that help people walk a different path.
So I did what any sensible person with a full-time job and four kids would do (lol): I started a law firm as a side hustle. After a year or two of little sleep, the side income matched my day job. I jumped.
Some months were $30,000. Some were $0—with four kids and a mortgage. That’s not a straight line; that’s real life.
Then life threw us a curveball that drew a bigger circle around everything we value. My wife and I both lost our dads in 2002. In 2022, Las Vegas authorities called: they’d identified her dad’s remains, found in Lake Mead. We flew to Vegas for a memorial, and while we were there my wife said, “Doesn’t this feel like home?” Three months later, we closed the business, sold the house, and moved. (She’s a little scary—in the best way. If I argue with the cell phone company, I pay them. If she argues, they pay us.)
My law license didn’t transfer, so I took a corporate trust officer job. Big clients. Big names. Big responsibility. It was cool—and I still missed the change-making conversations. Later I got licensed in Nevada. Today I’m in-house counsel and a trust officer. I help write policy, make decisions, and protect families when life goes sideways.
All along, I’ve been a law + art guy. I launched podcasts and blogs, made coloring books, and started an Etsy shop selling artwork and phone cases. None of this was a master plan. It was a series of honest experiments.
Truth: Your career probably won’t be a straight line. The sooner you get comfortable with “try → learn → pivot → repeat,” the more freedom you’ll feel.
Myth #2: Failure is the enemy
When I was younger, failure felt like proof I wasn’t cut out for something. If a project flopped, I felt embarrassed and discouraged. Maybe you’ve felt that too.
But the people we admire fail—a lot. They just don’t stop there. They use failure as data.
I’ve launched creative projects that went nowhere, written posts barely anyone read, and invested time and money into ideas that fizzled. I’ve had “$0” months (hi, July 2021). And yet every “failure” handed me a gift: better writing, sharper design, real e-commerce chops, tougher resilience, clearer direction.
“Failure isn’t the opposite of success—it’s part of success.”
Quick reflection (10 seconds): Think of a time you failed—a test, tryout, audition, speech, goal. What did you learn that you wouldn’t have learned by playing it safe?
That lesson is gold. Keep it.
Myth #3: Success = money
Money matters. It pays for food, houses, and vacations. It gives options. But after years as a trust officer, I’ve seen families with more money than they could spend who are miserable—and families with modest means who are thriving.
The difference is not the number in the bank. It’s alignment: values, relationships, and purpose.
When I picked a legal specialty, I could’ve chased the highest salary. I chose estate planning because my own story—losing both parents young—lit a fire to protect families. That meaning changed everything.
Try this question: If money weren’t an issue, what kind of work would you choose? Your answer is worth paying attention to. It’s a compass, not a cage.
Four lessons that actually help
1) Start small (and start now)
My first ventures weren’t flashy. My Etsy shop is not a rocket ship. But it taught me product uploads, merchandising, customer service, and organic traffic. And it still sends a little money every month—without me touching it since 2022.
You don’t need a million-dollar idea to begin. Mow lawns. Design t-shirts. Sell baked goods. Start a YouTube channel. Take one small step, get one real lesson, and stack them.
Mantra: Beta now. Better later.
2) Your story is your greatest asset
When I sit with estate planning clients, I’m not just “a lawyer.” I’m a kid who lost both parents and knows what’s at stake for other kids. That story builds trust. It differentiates you more than any bullet-point list of features.
Bring your story into applications, pitches, and posts—it’s the difference between “another service” and the person I want to work with.
3) Stay creative
For a long time I thought I had to be either a serious lawyer or a sensitive art-and-writing guy. Turns out, combining both is my edge. The creative practice keeps me human. It feeds ideas back into the “serious” work and guards against burnout.
Love math and music? Science and social media? Combine them. There are eight billion people on Earth; you only need a few hundred true fans to build a meaningful living.
4) Serve first
Before meetings, blogs, podcasts, or client calls, I don’t ask, “How do I maximize revenue?” I ask, “How can I make someone’s life easier, happier, or better?” When you serve first, trust follows. When trust follows, so do opportunities.
Simple rule: Who can I serve today, and how can I serve them well?
Advice to my high-school self (and anyone feeling stuck)
- Try things sooner. You’ll never feel perfectly ready. Make version 1 so you can make a better version 2.
- Don’t be afraid to look silly. People aren’t replaying your outtakes in their heads—they’re thinking about their own. Beta now. Better later.
- Learn money early. Budgeting, saving, index funds, basic taxes—money is a tool, not the goal. The earlier you learn the tool, the more freedom you get later.
- Focus on relationships. Your ideas will change, your jobs will change, your bank balance will change. Your reputation and the trust you build will open doors you can’t open alone.
- Choose optimism. My personal motto: It’s gonna be great. Not because everything is perfect—but because optimism keeps you moving when things aren’t.
How to find your next right step (today)
You don’t need a 10-year plan. You need one honest next step. Here’s a five-minute framework:
- Name your curiosity. What keeps tugging at you lately? (A skill, topic, or problem you want to solve.)
- Pick a tiny experiment. A micro-action you can do in under an hour. Examples: outline a 3-minute video, list 10 potential Etsy products, draft your first newsletter, email one mentor, or price-check a certification.
- Put it on the calendar in the next 72 hours. (If it’s not scheduled, it’s not real.)
- Do it, badly if needed. No perfection. Ship version 1.
- Debrief with two questions: What worked? What did I learn? Then pick the next experiment.
That loop—curiosity → tiny experiment → learn—is how you build a career that supports your life, not a life that props up your job.
A quick personal note
If all this feels vulnerable, it is for me too. I’m building, right now, a coaching/course platform to help people craft careers that support their lives. I’m a full-time in-house counsel and trust officer. I have a family I adore. I’m stacking 25 extra hours a week to build something meaningful and sustainable. I’m not “there.” I’m on the way—just like you.
And that’s the point. You don’t have to have it all figured out. You just have to take the next right step with the courage you’ve got today.
“Don’t build a life that only supports your job. Build a career that supports your life.”
Your turn
- Comment: What’s your next right step—the tiny experiment you’ll do this week?
- Reflect: If money weren’t an issue, what kind of work would you choose? What’s one small way to taste that this month?
- Share: Know a student, grad, or career-switcher who needs this? Send it to them.
Beta now. Better later. It’s gonna be great.