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Rewirement

Often, when I introduce myself, I say, “I have grown up in tech.” It’s true. I’ve gone from Product Manager to CPO. I’ve co-founded and led a venture-backed startup all the way from idea to acquisition. My equity gained value more than a handful of times, which is a rarity in the world of startups. I’ve gone from leading a bootstrapped company with three employees to teams of hundreds at a publicly-traded monolith doing billions of dollars in revenue. I’ve seen and experienced a lot. And yet, I knew that I was done and ready to call it quits over a year ago. I recently left my executive leadership position at Mailchimp and, in doing so, I left a nearly 30-year career in tech.

It was bittersweet. While I was ready to close the door on the day-to-day grind of corporate life, I wasn’t ready to retire. Besides being far too young for that, there’s more I still want to do. I’m at that point in my career where I’ve become a “post-achievement professional.” It’s a new category of people who have jumped off the corporate ladder and stopped chasing money, titles and accomplishments, opting instead for family time, balance, health, and passion projects. We are people who have gained financial independence yet still have drive and a desire to work, but it’s no longer the biggest part of our lives. My uncle says I’m not retiring, I’m rewiring.

It’s relieving to finally feel like I have nothing else to prove. What I do have, though, is valuable knowledge that I think is useful in helping the next generation of business leaders create a more fulfilling and humane work environment by creating companies that produce products and services that add value to our world. Our new book, The Intentional Organization, coming out in early 2025, goes into more detail about that. In general though, I approach all aspects of my life with intentionality.

So far in my rewirement, I’m prioritizing my health. It starts with finding a work schedule that strikes a balance between doing and not doing. Studies on well-being indicate that while being too busy creates unhappiness, being not busy enough creates a vacuum that fosters boredom and idleness. Certainly, with more space in my days, I can be more present but I also have to choose to be. With my coaching practice, for instance, I don’t schedule clients on Mondays and Fridays. I don’t want to have to jump into my week so quickly with back-to-back meetings. In fact, I don’t ever want to be in back-to-back meetings again regardless of the day! Instead, I can think about the work ahead and how to approach it. I can write, read, think, or not do any of that and go for a walk, meet a friend for coffee, or go for a hike or gravel bike ride. Then, I ramp into a different zone midweek for clients and pool them together for consistency of energy before slowing down again at the end of the week to tie up loose ends. By doing so, I can leave work behind me on the weekends and be fully invested in my time with my family and my community.

I also joined a gym in order to gain strength, I’ve recommitted to my yoga practice that fell off my schedule because of time constraints, and I signed up for a long trail run in Mammoth in September. The last few years of pandemic-induced overindulging and under exercising, combined with midlife hormonal changes, plus the high stress of selling a company and becoming an executive in someone else’s company, well, let’s just say that my waistline suffered. Having a big goal of a race on my calendar is a great way for me to stay committed and motivated.

With this next chapter, there are external and internal pressures and experiences that I am navigating. Externally, I have more gray hair, a few wrinkles, and way more skincare cream and sunscreen than ever before. I attend more funerals than weddings. I endured the death of my parents. I experience ageism. Internally, I recognize that time is precious, and I find myself thinking about the remaining ~30 years (and hopefully more!) I have on this planet. I am more aware of the fragility of life and my health. I am keen to reconnect with friends and loved ones in more meaningful and consistent ways. I don’t feel pressure about any of this. I simply value these things way more now. I don’t want to take them for granted. I want to stay current with the people I love.

As I embrace the fortune of being in post-achievement and being able to rewire, I’m able to look and see things differently. I’m still curious, but now I feel more wise. So much of what I once valued no longer feels important, and that’s relieving. There’s been a perspective shift that is calming. To me, transitions in life are sacred experiences that we, too often, rush through to get to what’s next. I’m not in a rush or hurry, and while I love being semi-retired or rewired, I’m contemplating going back to school to get a PhD and doing some advanced coach training and certification work. I very much enjoy having an outlet in executive coaching that stimulates my brain and gives me a focus area. I’m blogging more. I’ll be speaking at a conference in NY in early September. I’m thinking about starting to write my next book. I’m expanding my coaching business and thinking about adding new services and workshops. I’m getting involved with local entrepreneurial and coaching communities. And, lastly, we’re prepping for the launch of our book next year. Going on a book tour, y’all! This may sound like a lot, but I have so much more time and blank space to dream and create. I don’t think I’ll ever completely retire. It’s just not in my DNA. And that’s why rewiring just feels right.

Oh, and one last thing, I’ve become reacquainted with the great art of napping. My animals (three cats and a dog) are the best mentors I’ve ever had in that department!

Reflections

Reflect: Find a quiet spot, set a timer for 30 minutes, and ponder and journal where in your life you are transitioning or about to be transitioning. Is there a birthday, anniversary, or other event coming up? Are you contemplating a change in your life or career? Is there anything that you might be ending, giving up, or starting? Is there an old idea you need and want to let go of?

Assess: Write down exactly what is ending. This isn’t just the actual circumstance and specifics, but it is also the personal and internal feelings (excitement as well as fears) about what is ending. Next, write down what is in the middle of this change. How can you best honor and learn from being in this transition? What is important to notice? What do you need to let go of to fully embrace the transition? And lastly, write more about what is beginning. Again, pay attention to what specifically might be beginning–what is new internally and externally.

Do: Meet with a trusted friend, mentor, or advisor and share your reflections and assessments. Be open and honest about your fears, your excitement, or whatever emotions are coming up for you as you contemplate this transition. Ask for support and accountability. Commit to meeting again after 30 days to share new observations and learnings.

Further Reading/Listening