Trail & Error: Issue 001 – Taking the First Step

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On Ambition & Success

I’m not ambitious—or at least not in the way most people think of ambition.

From 2016 to 2019, I worked at Pinterest during its rapid growth phase, bought and remodeled a house, got my MBA from Berkeley, and raised two kids under five—all while barely sleeping or exercising. To many, that might seem like traditional ambition, but for me, it wasn’t about climbing the career ladder.

It was about building a life on my own terms.

Success, to me, isn’t financial. I lean on Seth Godin’s wisdom: "Instead of wondering when your next vacation is, maybe you should set up a life you don’t need to escape from."

My version of success means being present for my three kids, investing in my health, having time to think, to read, and to follow my curiosity. It’s not about status—it’s about fullness.

One model I’ve embraced is the "portfolio life," beautifully explained by Christina Wallace in her 2023 book. Unlike the hustle culture-driven “portfolio career,” this is about something much bigger. As Christina says, "We need to allow highly ambitious professionals to have chapters of life that require reallocation of their time, talents, and ambitions."

I couldn’t agree more.

In a portfolio life, you fill your life with a variety of meaningful experiences, cultivate multiple income streams, and expand your identity beyond your job. You give yourself permission to be ambitious in unconventional ways.

So, is wanting a big, portfolio life ambitious? Maybe. Just not in the way most people expect.

Trailblazer of the Week

Today’s story is about a friend of mine who’s taking a bold step into the unknown—right after returning from maternity leave.

For the past decade, she’s been laser-focused on her career, but now she’s at a crossroads, unsure of what’s next. After long talks with her partner and mapping out their finances, she’s decided to give herself 6-9 months to figure it out. She knows she wants to pivot to a new industry but doesn’t have a perfect plan—and that’s okay.

At the top of her list for this next chapter:

1. More flexibility

2. A mission she believes in

3. Living a life aligned with her values

She’s been grappling with what “success” means now. For years, she equated success purely with financial gain, but she’s starting to realize that’s only part of the story. Her husband often helps her stay grounded when she falls back into old definitions of success—which might not always feel fun, but it’s necessary.

Oh, and here’s the exciting part: she’s agreed to beta test my new life design product once it’s ready! 🎉

Sometimes the first step is simply creating space for the unknown. Whether it’s quitting a job, setting new priorities, or just redefining success, starting with intention can lead you to doors you didn’t even know were there.

Oops, I Did It Again: Start, then Learn. Don’t Learn, then Start.

Guys, I have a confession: last week, I spent too much time learning.

I’ve been planning, ideating, and envisioning how all sorts of ideas will play out.

This is an old pattern, and it’s super common. I wasn’t actually taking steps to make them happen.

This week, I decided to break the cycle and move from thought to action. Here’s 4 things I did:

1. Chose a name for an upcoming product offering.

2. Built a website.

3. Created this newsletter (and sent out the first issue!)

4. Made a list of people who can help my business idea come to life—potential investors, freelancers, advisors, client referrers, and clients—and started setting up time to talk to them about my idea.

5. Talked to 3 people on the list about my business idea (and set up 3 more meetings for next week!)

I’ve realized that action is the cure for my overthinking. With each concrete step, I get a little more clarity. As I’ve spoken to more people about my BHAG to help 1 million people build thriving careers and families that work for them (sounds crazy, I know!) my excitement is only growing.

The Oops Takeaway
Action = confidence boost.
Too much ideation = confusion.
If you’re feeling stuck, just start somewhere—clarity will build as you make progress!

Trail Mix

Try this!
Each day for the next week, write down 1 thing you're prioritizing for you.

It could be as small as taking a 10-minute walk, booking that long-postponed massage, or simply setting a boundary around your work hours.

Remember, the first step doesn’t need to be big—it just needs to happen.

It’s amazing what little shifts can do to get you started on a new path. You got this! 🙌

Until next week, i leave you with this gratuitous selfie of last weekend’s run with 2 friends (both named Trevor!) in Golden Gate Park.

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