Trail & Error: Issue 002 - Climbing the Second Mountain

Welcome to Trial & Error, where we help high performers design resilient, fulfilling careers by exploring the challenges, risks, and breakthroughs that come with building life on your terms.

Each issue will dig into what it means to redefine success, embrace failure, and create a purposeful career that aligns with your bigger life vision—even if you haven’t fully articulated it yet. This newsletter will provide practical insights and real stories to help guide your journey as you figure out what’s next.

I’d love to hear from you. What challenges are you facing in designing your life? What would you like to see covered? Reply to this email with your thoughts.

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Today’s Feature: How I’m Redefining Success On My Terms

In 2019, I made a decision that altered the course of my life.

At the time, I was thriving at Pinterest which had just IPO’d, I had recently completed an MBA from Berkeley/Haas, was a super active dad of 2 kids under 5, and had just sold a home I’d remodeled for a major profit.

Needless to say, I was emerging from an extremely busy period of life and was close to burning out. When my (now-ex) wife was offered a huge promotion that came along with a move to Europe, I gave notice at work, thinking I was making the right decision for our family. And having full confidence our finances were covered. Through financial diligence, a strong tech market, selling the house, and a healthy dose of luck, we’d saved a good chunk of change.

However, the move never happened, the job opportunity fell apart, and so did the marriage. And then COVID happened. It was a time of major uncertainty and upheaval.

Looking back, leaving Pinterest wasn’t just a decision for my family—it was a decision I made to build a career on my own terms.

I’d been working in online advertising for 12 years at that point, and I knew it was no longer for me. It wasn’t my path. Instead, I chose the unknown.

And while I couldn’t have predicted the full impact of that choice, it opened up a path that led to my wife Catherine, my third child, several roles leading marketing for creator economy and web3 startups.

And this same decision, to choose to follow my passion into the unknown, has led to my current (and very nascent) career stage helping others design more fulfilling lives on their own terms.

For the past 5 years, I’ve redefined success—moving away from external markers of achievement to build a life and career that are resilient, fulfilling, and aligned with what I, Sean, uniquely value.

I’ve come to call this my version of my life, Positive Sum. In this issue, I’d love to share more about what that means, why it’s important to me, and how you can help play a role in shaping it, and bringing it to life.

My Life Design Framework = The Positive Sum Way

My life design framework is called The Positive Sum Way. (Positive Sum is the name of my LLC. I think of it as the vessel for building a life that aligns with my goals & vision and just saying that out loud makes me happy.)

The Positive Sum Way has 4 key components. I’ll go through them one-by-one.

1. Resilience Through Intentionality:
   Success is not just about achieving external goals; it’s about building resilience in both your career and life. This means intentionally designing a path that allows you to adapt to changes and challenges. For me, moving into fractional leadership roles provided that flexibility, letting me focus on meaningful work while also prioritizing my family and personal well-being. I believe that in today’s rapidly-changing world, resilience is one of the most important values, and it’s a key part of my life design framework.
   

2. Purpose-Driven Career Design:
   Living a Positive Sum life does not require leaving your 9-to-5, unless your 9-5 feels like a grind. It’s about creating a career that fuels your personal growth and aligns with your values. For many high performers, the first mountain of success is about achievement and external rewards. But the second mountain, as David Brooks discusses, is about deeper fulfillment and purpose-driven work. This is what I coach my clients to work towards, and what I’m working towards myself with my business, Positive Sum.
   

3. A Portfolio of Roles and Passions:
   To build a Positive Sum life you should diversify your work and have multiple income streams. Today, my portfolio includes fractional marketing leadership role and coaching. And I’m actively pursuing some new opportunities right now to expand this list further. Having multiple sources of income provides financial security and help you feel more freedom to pursue passions that aren’t aligned with your work. With multiple sources of income, you can achieve a higher goal: multiple streams of fulfillment. Work should only be a part of your big, crazy life.
   

4. Flexibility Through Collaboration:
   Independence does not mean isolation. In fact, the Positive Sum Way involves frequent collaborating with others. I’m not a huge fan of the solopreneur concept, though I like Justin Welsh’s writing style and ethos. I prefer to emphasize collaboration with other freelancers and co-owners to create a flexible work environment where everyone benefits.
   
   To summarize, my version of the future of work is resilient, values-aligned, purpose-driven, diversified, fulfilling, flexible, and collaborative.

Climbing Your Second Mountain

Success, as I see it, isn’t about a title or salary. It’s about intentionally crafting a career that fuels your personal growth, relationships, and sense of purpose. The independent path I’ve taken has allowed me to balance meaningful work with flexibility, giving me the freedom to be present for my family and pursue passions beyond work.

This is the second mountain, a concept David Brooks describes in his book The Second Mountain. The first mountain is about self-centered success—climbing the ladder, getting the promotion, chasing status. The second mountain is a deeper journey of purpose, connection, and service. For me, the second mountain is about living a life where work fuels, rather than drains, my overall fulfillment.

The question is: What will your next mountain be? And will you make the climb?

Trail Mix: Small Steps, Big Progress

This week, let’s focus on taking action—even if it’s just one small step. The biggest breakthroughs often come from consistently showing up, not waiting for the perfect moment. Whether it’s in your career, personal life, or health, incremental progress beats hesitation every time.

Your challenge:
For the next seven days, write down one small action you’re taking to move forward. It could be something as simple as reaching out to a potential collaborator, scheduling that long-overdue meeting, or even starting a new hobby. The key is to take action, no matter how small, and keep the momentum going.

By the end of the week, reflect on those steps and see how far they’ve taken you. Remember, action builds clarity—the more you do, the more direction you’ll find.

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