Some Serious Thoughts About My Ambivalence Over Leaving a Fast-Rising Career to Become a Digital Nomad

I’ve read infinity blog posts by digital nomads who were sick of the 9 to 5 grind.

Tired of terrible bosses who made their dead-end job even more miserable than it would otherwise be.

Who felt trapped and desperate to get away from the grind. Or felt burned out by the high pressure and stress of their traditional career.

So, they chucked it all to become a digital nomad to escape their traditional job nightmare.

That’s NOT my story.

I Loved My Career

I left a job that I really loved. I left behind a CEO that I consider a mentor and a champion and a friend – someone who handed me challenge after challenge with little more instruction than pointing his finger and saying, ‘Make a plan and then take that hill,’ then providing as much or as little support as I asked for to get the job done. Who saw my potential and harnessed it.

I left behind a couple of teams made up of amazing people (who I would have killed or died for!) that I had been leading. And those teams were just hitting their stride and taking their remit to the next level.

I left a career I loved as a fast-rising executive with a trajectory to be a CEO myself within a (very) few years.

And yet I left.

My Life, My Rules

I’ve described in this blog how the life I have lived has made me somewhat risk-adverse. Despite that – and everyone who has worked with me knows this – I’ve never quite lived by ‘the rules.’

If something – an institution, a plan, a policy, a notion, a rule, an instruction – makes no sense to me then I am quick to challenge it…often aggressively…maybe even too aggressively.

And to me, the idea that you are supposed to work hard in an office for 40 years accumulating as much success, money and things as possible then retire when you are in your mid-60s never made much sense to me – no matter how much I was enjoying the process.

There is too much of the world to see. Too many experiences to be shared.

Knowing this about me, when she was talking me into it adopting a digital nomad lifestyle, Lisa originally referred to our decision to become digital nomads as a ‘mid-career retirement.’ And I appreciated that.

But that’s not REALLY what it is.

What it really is is an attempt to see if we care to permanently change the way we live our lives. So, I forced myself to take stock of the notion of possibly never achieving the career goal I always assumed I would: successfully leading an entire organization or at least a massive team.

In taking stock, I realized that what I loved so much about my career was what I always referred to as ‘smart people getting shit done.’

That and building and leading great teams.

But especially the feeling of accomplishment when a benchmark is hit or a project succeeds; that’s like crack to me – give me a taste of it and I’ll do whatever it takes to get more.

But then again, that’s exactly how I’ve always felt about travel: a little is never enough. Hell, a lot is never enough.  

So ultimately my decision to leave a job and career that I loved to try out digital nomadism came down to the notion that I could continue to get the rush of professional achievement by working with Lisa on growing her business, writing this blog and doing some remote consulting – all while at the same time pursuing my other passion of travel full time.

And – worst case (any Chief Strategy Officer worth his or her salt ALWAYS does worst case planning!) – we end up resuming our traditional careers after the adventure of a lifetime.

Regrets? Naaaah!

So obviously at this point I am all-in and am 100% certain it is the right choice.

Still, as we continue this adventure, I still often find myself having a surprisingly difficult time letting go. I’ve been checking in with former colleagues every few weeks and still read the industry trades.

I don’t know how long that will last, but I’m at peace with it if it never stops.

After all, I spent 15 years at the same organization and, just like my kids who I spent 17 years raising, maybe I’ll always care and want to know that they are doing well and finding success. No shame in that, right?

Lisa and I met a traveler from Oregon here in Chiang Mai over dinner one night (this seems to happen to us a lot in our travels – we end up chatting with folks at adjacent tables over dinner) called Summer who had been traveling for a few months.

Summer and I ended up talking about this topic a lot: the emotional complexity of shifting from the corporate paradigm to the digital nomad paradigm.

Well, as longs as we can keep selling on Amazon we should be OK. Shameless plug alert – the unicorn backpack party favor bags that I sourced and project managed needs increased profitability!

But they are SO CUTE:

And this sure does feel right.

I’m with the smartest person I know getting shit done AND traveling full time. If that’s not having my cake and eating it too then I don’t know what is.

As my mentor would always say, “Onward and upward!”

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