Now What?

So I’ve been trying to figure out what to do with my life.

You might be thinking: What? Tom, you’re turning 60. Your life is pretty established.

BUT, my challenges are:

    • I’m fit and healthy, and am confident I’m going to live a long life. (My parents are 30+ years older than me and still alive.)
    • I’m working in tech (earning good money) — but I’m kind of sick of it.
    • My real passion is around things more creative. If I were confident (at 20) that I could have had a well-paying career doing something artistic (for example), I would probably have gone in that direction.
    • I’m a smart guy (very math-y) and am well suited for working in tech.

So here I am approaching traditional retirement age, and thinking: Is it time to walk away from what I’m doing, and start a ‘second career’? I’ve been working for about 35 years. I could live another 35 years (or more) and have a completely different second career — starting now.

Just thinking about the possibility of walking away from my day-to-day grind is refreshing. My current role is very much reactive — I essentially do what needs doing based on current circumstances. I feel in some ways a ‘pawn’, with my actions determined by a set of chaotic individuals — who do unpredictable things, which I often need to set right.

The challenge is that — as I said above — I’m earning good money. HOWEVER, at the end of this calendar year (now only 3 months away) my stock income drops off by quite a bit — since I’ll have been with my current company for four years, and will have pocketed the last of my incoming stock grant. So then… what?

Do I look for a new tech job (with similar income) which will at least provide different challenges? Or do I pursue something completely different (ignoring the money inflow) that makes me (more) happy? One external opinion is: our financial adviser has told us, given our net worth and post-retirement plans, I could retire now — and we would have enough money to fully enjoy ourselves (travel, etc). Further, it would be tragic if I delayed retirement, but then one of us got sick (or worse) and we couldn’t enjoy our later life.

I don’t know what the answer is, but I’m leaning toward:

    • Walking away from my current  job at the end of the year
    • Assessing other opportunities in tech (to see if there might be one that pays well, but is less bothersome and/or consumes fewer hours)
    • Or stepping away entirely, enjoying ourselves, and returning to the workplace — only as/if needed 

I fortunately look/act younger than I am. So if I needed to re-enter the work world (after being away for X years), I could probably pass as someone not on the edge of calling it quits.


Couple of additional thoughts:

    • If neither of us are working, then we’d have to pay for health coverage out of pocket. We need to ensure this cost is part of the decision.
    • I get 75% of my annual bonus in April — which might encourage me to stick around until then.

Leave a Reply

Your email address will not be published.