Lessons Learned Working With My Career Coach

Reflections on growth, leadership, balance, and building a career with intentionality.

I’ve had a lot of big life changes this year. My wife and I welcomed our first child. We moved out of our hometown (to Portland, Oregon!) to try something different. We sold two homes and bought a new one—sight unseen!

I am not a risk-taker.

You probably don’t believe me 🙃.

With so much change in motion, it felt like the right time to take stock of other parts of my life, including my career. I decided to work with a career coach to reflect on my career's past, present, and future—to be more intentional about the path I’m taking and the career I’m building. Long story short, it was an incredibly valuable experience. I decided to take some time to document and reflect on the lessons I learned along the way.

Lesson 1: Your Comfort Zone Can Be a Trap (and Growth Lives Outside It)

It’s tempting to raise your hand for the things you know you’ll knock out of the park. Operating from a place of comfort allows us to be reliable, predictable, and effective. But through coaching, I realized that just because you're good at something doesn't mean it’s where you’ll grow—or even find fulfillment. And it might not even be where you’ll make the biggest impact.

For me, this insight first came into focus when I became a manager of managers. My first instinct when I saw a struggling project or a team that wasn’t firing on all cylinders was: “I can fix this! It’s second nature to me now! It’s how I climbed the ladder in the first place!”. I’d want to jump in and help make it a success. But that approach limits you. It doesn’t push you into new and challenging situations where you can actually grow. It’s a sign that you’re retreating to a place of comfort instead of doing the hard work of helping someone else succeed. It’s like solving your child’s homework problem for them: you might help them get a good grade today, but they’ll struggle tomorrow because they didn’t learn to work through the problem themselves. Leadership is no different. It’s about coaching and nudging, not taking over.

Instead of taking over, I learned to point out observations, ask questions, and put on my coaching hat. Be a sounding board. Step in only when things are completely off the rails (it happens 😅) or when the risk is too high to let it be a learning moment.

Consider this instead: Next time you think about raising your hand for something because you're good at it: don't. Let someone else take the starring role. Mentor them through it or offer to play co-pilot. You’ll still learn, but in a different way: by coaching, stepping back, and amplifying someone else’s success. An added benefit here is that it takes up less time and mental bandwidth to be a supporting actor. You'll leave yourself with more time for high-leverage work.

Seek out roles and opportunities where you don’t already have the answers. Those are the ones that will stretch you, challenge you, and ultimately build a career full of meaning, not just competency.

By embracing this mindset, I also realized how important it is to wander bravely into the unknown. If you already have a plan or approach in mind for how you’d tackle something, chances are you’re already coming at it from a place of comfort. Instead, look for challenges that leave you a bit lost in thought, where someone else might even mentor or coach you. This approach broadens your skillset and builds resilience, which benefits you and the business in the long run.

The payoff is versatility. It conditions you to approach unfamiliar territory without fear and face new challenges both as an individual and as part of an organization. Over time, it’s how you grow—toward opportunities and outcomes you didn’t even know were possible.

Lesson 2: The Outsized Impact of Leaders (and Why the Bar Must Be Higher)

Leadership positions are high-leverage roles. The people you place in these positions have an outsized impact on your organization’s culture, morale, and overall direction. This means that your leadership hires—whether technical leaders or people managers—must be scrutinized more heavily than others. The stakes are simply higher. The old saying goes: People don't leave jobs, they leave bosses.

Hire only “strong yes” candidates, and be doubly sure for leadership hires. This means going slow in the interview process, however painful, and digging deep to understand not only the candidate’s capabilities but also how their values align with your organization. Leadership is more than competency—it’s about influence, intentionality, and setting an example, especially when no one is watching.

One specific pitfall to avoid is what Will Larson calls "The Flying Wedge". This happens when a leader brings in a group of former colleagues as a "proven team." It might seem harmless—after all, they’re proven performers in the leader’s eyes—but it often creates problems like groupthink, a lack of diversity, and eventually even cultural fractures. Larson describes it as “clearcutting the existing culture” to replace it with one the leader is comfortable with. This shift signals to others that they must either adapt or leave, creating long-term instability. While referrals can get someone in the door to be screened, they should never bypass your standard hiring practices. Stick to your high bar, even—or especially—with strong recommendations.

The reason this is so critical is that culture is contagious. A single values mismatch in a key leadership role can shift your culture in ways that are hard to slow or reverse. This is especially true in senior positions, where people naturally emulate their leaders. If you bring in someone whose style doesn’t align with your values, you’ll see ripple effects in how people interact, make decisions, and even how they approach their work.

Consider this instead: Focus on deliberate, aggressive coaching when you notice a misalignment. If someone isn’t on the same page culturally, don’t wait to address it. You can teach new skills or coach someone out of bad habits, but you can’t fundamentally change how someone operates at their core. Swift, decisive action is necessary if you realize you’ve made a mistake in hiring.

Finally, remember that leadership is about more than hitting metrics or executing plans—it’s about modeling behavior that inspires others to do their best work. Invest in leaders who reflect the values you want to amplify across your organization, and you’ll build a culture where people thrive.

Lesson 3: Personal Growth Fuels Professional Growth (and Vice Versa)

It’s tempting to want your career to fulfill every need you have—we spend so much of our lives working! But trying to get all your professional satisfaction, personal validation, and growth from a single source often sets you up for disappointment and masks gaps in other areas of your life that need attention.

I explored these topics with my career coach during an exercise we partnered on, and pulled on some ideas and other things I'd been thinking about since I originally read Lara Hogan's piece about building a “Manager Voltron”. I'll connect the dots. Stay with me 🤖.

The “Wheel of Life” exercise with my career coach was a turning point. I evaluated different areas of my life—physical health, relationships, home environment, professional growth, and more—by marking where I was today versus where I wanted to be. The gaps revealed opportunities, but the key takeaway wasn’t about fixing everything—it was about prioritizing. For example, since moving out of state, I’ve focused on my wife and daughter over friends and extended family relationships. I’ve deliberately chosen not to close that gap right now, and that clarity has been freeing.

Your priorities in your career are similar. Let's go back to the "Manager Voltron". If you didn't follow the link and read the post, it’s the idea that it's unlikely—even improbable—that your manager can fulfill every need you have. Accepting this, you assemble a metaphorical “Voltron” of mentors and peers who collectively support your growth. I've extended this idea further to determine that no single part of life—whether work, parenting, or hobbies—can meet all my needs either. Balance comes from diversifying your sources of fulfillment.

For instance, I enjoy coding and writing (surprise!), but I’ve learned to keep them separate from work. Coding is now a creative outlet for me rather than a job requirement. This shift has helped me enjoy it more, free from the stress of deadlines or deliverables. Similarly, writing blog posts or participating in leadership discussions online or in small peer groups scratches an itch for creative and professional growth that my day-to-day leadership role doesn’t always satisfy.

Becoming a parent has also reshaped my priorities. When I held my daughter for the first time, it was a profound reminder that much of the chaos of work is fleeting. My wife often reminds me that “this is a season of our lives” and it isn't forever. Similarly, careers are part of life; not the entirety of it. To maintain this balance, I set stricter boundaries now: no scheduling over lunch, no unwarranted overtime or weekend work, and clear start and end times for my workday. I realized some time ago that work is never truly “finished”. With that realization, and the more recent realization that family time is sacred, I set the boundary that I no longer let work bleed through.

Consider this instead: Be intentional. Personal growth is professional growth, and the experiences you cultivate outside of work—whether parenting, hobbies, or relationships—will make you a better leader and professional. Set boundaries, diversify your sources of fulfillment, and understand that balance isn’t about giving everything equal time. Instead, it’s about giving the right things your time and energy when they need it most.

Lesson 4: My "Why" of Leadership (and Using It to Find the Right Role)

One of the things my coach pushed me on was diving deep into the "why" of leadership. I’ve always been fascinated by understanding the motivations of leaders—why did they choose this path? What keeps them going? Charity Majors' famous "Engineer/Manager Pendulum" post shaped some of my early thoughts about how my career might shake out, but over time I realized that I find the challenges of leadership more engaging and fulfilling than IC work. I want to climb the ladder and I've spent time exploring why I have that drive.

Leadership challenges are inherently people challenges, and I’m a relationship-builder at heart. Connecting with people, understanding shared goals, and finding ways to achieve them together motivates and energizes me. There’s a unique satisfaction in creating order from chaos, aligning a group around a common cause, and empowering and enabling everyone to succeed. Even before formally moving into leadership, I sought out opportunities to mentor, organize, and create structure. It’s been a natural evolution.

But my decision to embrace leadership was also shaped by a belief that I could do better. Not every boss I’ve had was terrible—some were excellent—but I saw firsthand how much influence leaders have over team morale, effectiveness, and culture. As an IC, I sometimes felt powerless to change the things that frustrated me. Leadership offered the opportunity to build trust, autonomy, and an environment where people could thrive—the environment I’d always longed for myself in those shoes. My goal has always been to create the conditions for people to do the best work of their careers. It’s ambitious—maybe even pretentious—to think that I could help people reach their peaks, but it’s what keeps me motivated.

This focus on impact and alignment has also guided how I target roles:

• Avoiding player-coach roles: I bowed out of several interviews where it became clear the company wanted a part-time developer in a manager. I want the time and space to hone my craft as a leader, and I know that splitting focus compromises both leadership and technical contributions.

• Seeking growth-stage organizations: My strengths lie in helping organizations and individuals navigate growth, scale, and change. I looked for companies at inflection points where I could shape both the culture and technology as they evolve.

• Aiming for large-group leadership: I aspire to climb to VP or C-suite roles—not immediately, but eventually. That means finding opportunities to lead cross-functional teams, tackle strategic challenges, and grow my influence across the business. I looked for companies where I could build breadth and depth while scaling my impact.

• Focusing on outcomes, not outputs: I dug deep during interviews to understand how companies measure success. If I hear too much about "velocity" or "roadmap adherence" and not enough about impact, I take it as a red flag. I want to be part of an organization that prioritizes autonomy and business outcomes over arbitrary metrics and hollow outputs.

Ultimately, leadership gives me opportunities to solve complex, organizational problems and help shape both the culture and direction of an engineering function. I measure my success not by the size of my team but by how effectively I can maintain and scale my principles and empower others to thrive. As I grow, I’m focused on tackling new challenges—broader delegation, vision alignment, and cross-functional strategy—so I can continue to lead with impact and integrity.

Lesson 5: Balance over Burnout (and Building a Sustainable Career)

Early in my career, I couldn’t fathom a trajectory that didn't resemble an arrow pointing straight up. I was eager to grow as quickly as possible, and any obstacle or glass ceiling left me frustrated. I coped with this frustration by changing roles whenever I felt stagnant. At the time, it made sense—I wanted to grow faster than some organizations could support, and I wasn’t willing to settle for opportunities that didn’t align with my career priorities.

Now, my perspective has shifted. I regularly ask myself one crucial question: "Am I learning?" If the answer is yes, I know I’m on the right path. If not, I take time to reflect on whether I’m operating from a place of comfort or if external circumstances are holding me back. I’ve had roles where I looked back and realized the experience wasn’t valuable because I wasn’t growing. It’s a hard pill to swallow, but these moments have taught me to focus on intentional growth.

For example, I left more than one job where I explicitly stated in interviews that I needed progressively more challenging leadership opportunities to feel fulfilled. In both cases, I was assured those opportunities existed, but they didn’t materialize in the ways I expected. I now evaluate roles more critically, looking for evidence of growth opportunities. Growth-stage companies are often ideal because they naturally create new challenges and roles as they scale. Layers of management emerge, specialized roles are created, and opportunities to explore new areas abound.

But growth isn’t just about moving forward—it’s also about balance and intentionality. There was a time in my life when money was my top priority, and I took a job primarily for the pay increase. I later regretted it because it didn’t align with my broader goals. Using the "Wheel of Life" exercise with my coach, I learned to evaluate what’s most important at any given moment and make trade-offs accordingly. Sometimes, it’s okay to take a step back in title, pay, or responsibilities if it aligns with your personal and professional growth priorities.

I even created an "Opportunity-Fit Checklist" during my recent job search, which helped me evaluate roles against my pre-determined criteria. This checklist kept me grounded, ensuring I wasn’t swayed by shiny new opportunities that ultimately didn’t align with my goals. It allowed me to stop being distracted by titles and other forms of prestige that ultimately don't move the needle for me in the long term. It’s a practice I recommend to anyone navigating career decisions.

Finally, I’ve embraced the idea of a "forty-year career," inspired by Will Larson’s post on maintaining a sustainable pace in your career. The concept is simple: focus on consistency and sustainability rather than burning out in short bursts. The popular "20-mile march" metaphor resonates deeply with me—maintaining a steady, predictable pace ultimately leads to greater achievements than sprinting and crashing. It’s the tortoise, not the hare, who wins the race.

So? Where do I focus my time and energy now?

I’m deliberately pursuing opportunities to prove myself as a large-group engineering leader. This requires autonomy, trust, and the ability to align my work with the company’s mission and vision. It’s not about empire-building—it’s about scaling my impact while staying true to my principles. And it’s about finding balance. By pacing myself and prioritizing sustainability, I can continue to grow and lead with purpose.

Wrap Up

Whether or not this inspires you to go out and partner with an awesome career coach, I hope it at least encourages you to be intentional about your career. Take time to reflect regularly—whether it’s once a month, quarterly, or whenever you feel stuck. Ask yourself if your current role is helping you grow and if you’re truly making the impact you want. If not, maybe it’s time to make a change.

At the end of the day, putting yourself first isn’t selfish—it’s necessary. No one is irreplaceable, and most of us won’t retire from the job we currently hold. The real goal is to find ways to grow, leave a lasting impact, and leave the places and people better than you found them.