Trail & Error: Issue 003 - Define Your Values (or Someone Else Will)

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 dives 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. I share practical insights and real stories to guide your journey.

I’d love to hear from you:
What’s one area of your life that you’d rebuild if you could start fresh? What challenges are holding you back? Just hit reply to this email—I’d love to cover more of what matters to you.

Define Your Values (or Someone Else Will)

In April 2012, I was laid off in a massive cut at Yahoo. Just 18 months earlier, they’d acquired Dapper, the startup where I was the 19th employee, managing half the company’s revenue.

But once the tech was integrated, they didn’t need me anymore.

I was caught off guard but relieved to be moving on. I jumped into a job search and, within two weeks, landed a role at a fast-growing startup. The relief was short-lived.

In a matter of months, I realized the company wasn’t a fit—I had serious ethical concerns about their client practices. So, less than six months after I started, I was searching again.

Looking back, I see the mistake I made in the rush to fill that void. I hadn’t evaluated whether the company’s values aligned with mine (or whether they were actually following them!)

I learned that if I didn’t make values discovery central to my interviewing process, I’d keep finding myself in places that didn’t fit.

Aligning with core values is a non-negotiable for me in work and life. Ignoring this has led to friction—and ultimately to failure. Every. Dang. Time. We’ll get into more stories in future issues. For now, here are 2 lessons:

Lesson #1: Define Your Values and Live by Them

Many people never define their values, and when they do, living by them consistently is tough. Here’s a path to making values your foundation:

1. Define Your Core Values
   Start by listing the principles that matter most to you. Look at times when you felt proud of your choices and moments of regret—these reveal what really drives you.

2. Use Your Values in Decisions
   Pause when making decisions and ask, “Does this align with my values?” Let your core values be the compass for major choices in work, relationships, and commitments.

3. Evaluate Alignment Regularly
   Every few months, check in. Are you living by your values? Realign where needed. It’s not about perfection; it’s about making progress toward a life that truly reflects you.

Lesson #2: How to Spot Unstated Values in a Company

In companies, the values on the website are rarely the whole story. To understand what actually drives decisions and culture, you need to dig deeper. Here’s how:

1. Ask the Right Questions
   Instead of “What are the company’s values?” try, “Can you share a time when the company faced a tough choice? How did leadership handle it?” This shows whether values guide real decisions.

2. Watch for Culture Cues
   If you get the chance, observe team interactions and communication. Are people transparent? Collaborative? Performance-focused? Culture often reveals what truly matters.

3. Research Leadership’s Actions
   Look into the leadership team’s track record, especially during challenges. Do they practice what they preach? Leaders who live by their values set a tone you can trust.

Concluding Thoughts on Values

Aligning with your values isn’t a one-time exercise; it’s an ongoing process that keeps you grounded and moving in the right direction. Whether you’re choosing a new role or re-evaluating your current path, leading with values pays off. It’s about designing a career and life that feel like your own.

The Turning Point That Changed Everything in My Life

A few years back, I hit a major turning point—one of those life-shifting moments where everything changes.

I had to strip things down and rebuild, focusing on what truly mattered. It wasn’t easy, and it didn’t happen overnight, but each step became a building block for something bigger.

Now, I help others do the same—brick by brick, designing lives that are more intentional and expansive.

For the first time, I’m sharing that story on video, getting real about what’s behind the work I do and why it matters. It’s a little outside my comfort zone, but connecting this way feels necessary.

Check out the video (3 min), and join me as I dig into what that turning point taught me and how I now help people build bigger, more fulfilling lives.

Trail Mix: Designing Your Life Rhythm

This week, let’s get hands-on with an exercise in life design. I actually just did this for myself last week, and I wanted to share it with you. This will help you turn your life priorities into daily, monthly and aspirational rhythms,

1. Write Out Your Vision
   Take 15 minutes and jot down everything you can think of that you really want in life—make it as detailed and vivid as possible. Include career goals, relationships, health, personal growth, and lifestyle. My list included things like: “I want to run at least 3 trail half marathons + Ragnar each year” and “I want to help people live better lives, every day” and “I want to write and read about things that interest me every day”. There were about 40 items like that.
   

2. Use ChatGPT to Organize & Distill
   Use the following prompt in ChatGPT (or a similar tool) to organize these elements into daily, weekly, annual, and aspirational rhythms:

   Prompt: “Help me design a life rhythm. Here’s a list of what I want to achieve or enjoy in my life: [paste your list here]. Organize these into daily, weekly, annual, and aspirational categories. The goal is to create a balanced rhythm that prioritizes my well-being, fulfillment, and long-term goals.”
   

3. Review & Reflect
   Look over your organized list. Does it represent the life you want to live? Finally, identify one or two rhythms that need more focus this week, and consider how you might start working toward them.

Thanks for reading Trail & Error! If you enjoyed this issue, consider sharing it with someone who might benefit. Let’s help people build resilient, fulfilling lives—one step at a time.