The hardest thing about leaving my previous career behind wasn’t saying goodbye to a large pile of unvested stock (at the time, much of my net worth) and a clear path to much more. That part hurt, but I got over it in a few months. My issue was deeper. Giving up my career felt like giving up my life, abandoning who I was and everything I valued at the exact time I was approaching ever higher impact and earning potential. It was gut wrenching and by far the hardest thing I’ve ever done, and I’ve done plenty of hard things. What got me through was clarity of the insight, and lots of grace. I knew that my time was up as far as that career went, but nobody could understand it (I barely did myself!).
Identity is a final boss in the game of life. We all have one, sometimes more than one. One’s identity takes on various shapes depending on life-stage, family background, DNA and understanding of what’s “True” about how the world works. Morphing and shifting with age. Mine grew stronger over time. Careers, particularly ones that start when you are young and last for many years with high intensity, they cast your career identity deeply. Like wet clay spun on a wheel, then kiln fired, an intense career can leave an impression that is indelible. A tattoo on the soul.
Of course, there is no actual tattoo. It’s all stuff of the mind. What makes identities tricky is that they serve a purpose. When you see yourself as a certain sort of special person, it makes the daily struggles, complexities and big challenges of life a bit easier to deal with. When you act as-if you are the type of person who just does things that a [fill in the blank for your job title here] does, you can find a level of energy and focus that otherwise is lacking. There is less decision fatigue. It creates a level of existential certainty that is comforting. There is also a self-soothing quality to resting in the warm blanket of a self-image, even if that image no longer fits.
There comes a time, however, when an identity is such a bad fit, no longer in line with one’s “Truth” (or even interests and values) that it is too painful to keep putting it on, like shoes that are far too tight. I left Microsoft after 13+ years even though a lot of things were great about my career. A nice office, wonderful team members, deep friendships, a big promotion on the horizon, exciting projects and stimulating big-picture conversations every day. Not to mention generous compensation and benefits. All of it was great, but I could not run away from a simple fact: I felt like I was living someone else’s life. It didn’t start like that, but in the final year or two it became clear that I’d transformed but my career had not.
I knew I needed to ditch my tech-career identity and, in a way, reinvent myself. I didn’t know how to do that, so I figured that a lengthy sabbatical would help. I was out of options! Turned out it worked miraculously, but not in the way I expected. Before resigning, I had conversations with three different senior-leaders at the company who reached out after discovering that I was leaving (all three were eventually promoted to C-Level leadership roles at the company). They asked if there was anything they could do to get me to stay. I said that it wasn’t about the job or the pay. I wasn’t going to work for a competitor. I just needed to do something else with my life.
After leaving, I thought that I could brute force my way into creating a new sense of purpose and self. I invested in workshops and coaching to make that happen both before and after I left Microsoft. I learned a lot from those experiences, but they utterly failed in helping me achieve my goal. What I needed was space and time to think and reflect. I took that time, far longer than I expected, and came out the other side with the realization that instead of trying to replace my identity with a new one, I was better off just letting go and allowing life to fill up the space.
I had no idea what I wanted to do for work long-term, but I did know that many friends and friends-of-friends were reaching out for career advice and counsel. I also needed flexibility in my schedule (both in terms of working hours and location), and that ruled out full-time roles at other companies. (This was before the remote work revolution). So, I hung up my shingle as a coach by posting a few messages on social media. A few clients hired me right away, and I was off to the races. Eventually, I set up my LLC, website and figured out how to get paid.
Along the way I radically cut my expenses, selling my house (along with most of my stuff) and did everything I could to ease the financial burden to give my new career a fair shot. It took three years before I was making enough income to get back to a more normal lifestyle, buying a new house and all the things a growing family needs. In hindsight, three years was nothing, though it felt like forever at the time.
Now, thirteen years after I said goodbye to Microsoft and almost twelve years since embarking on my vocation as a coach, I’m about six months into my second sabbatical. I’ve been questioning everything again and getting more comfortable with seeing how it feels to live in that space of being a “nobody” for a while. Not an executive coach. Not defined by what I do, but just being who I am. It’s not easy.
Identity is a sticky matter. I’ve never had a tattoo, but I’ve heard that removing them is painful and laborious. The metaphor fits! One reason is that the mind loves to play with identities, and the world loves reinforcing them. It’s an ego boost to feel important, that you are a “somebody.” Then there is the practical reality of how people tend to engage with others, particularly as a man who is about to turn 47, work seems to be everything for my demographic!
Every new acquaintance asks: “What do you do?” Those who know I’m on sabbatical ask: “When are you going back to work?” Friends ask: “How is business?” Through it all I just try to be relaxed and comfortable not having to hang my hat on a job or a title. I also don’t have the luxury of sharing about the exotic adventures I’ve been on, as my last sabbatical was full of those but this time, I’ve had exactly zero!
I’ve mostly been a homebody who is not working, and increasingly OK with it. My typical response when people ask how my sabbatical is going is: “It’s been good. I’m spending a lot of time with my kids.” This is about as close to the truth as I can get in a couple sentences. It’s also what I was looking for when I started it.
Yes, I will return to working reasonably soon. I have plenty of energy and a desire to add value to the world. Coaching still feels like the right fit for me, more of a calling than a job, but how I do it might look different than how I did it in the past. I’m finding increasingly high value and freedom in a lighter, but not empty, calendar. I’m also more motivated to meditate, think and write on my own terms. So, I’m following that vein. That old sense of identity, that invisible tattoo with all its compulsions to be busy and effective, has faded even more this year.
Life has swept in to fill the blank space, mostly in the form of my two energetic kids and dog. They desire and appreciate my full attention. I’m realizing that this will not always be the case. They won’t always want daddy to be around. Right now, I’m a superhero in their eyes (sometimes a villain!), and between the tantrums and the dramas, it’s not lost on me how special this time of life is. I’m in no rush to skip past it.
Those last words are something my former self would have really struggled with. In my teens, twenties and thirties I was always skipping past the mundane and everyday stuff, striving towards the next goal, promotion or adventure. But life has no KPIs or management reviews to tell you if you are on track. I’m realizing that the real work of life is to deal with what is showing up right now. Sometimes that means embracing a big project, job or adventure. Other times, as is the case for me, it’s heading off to pick up the kids. Speaking of which, I need to go do that now. Until next week…
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