I've stopped planning and started looking "backwards"
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This is the first-half of a two-part blog on goals, learning, and jobs.
My five year plans have always been wrong
At some point in my life, someone told me to have five year plans. "What do you want your life to look like in five years," was the prompt. I can safely say that my five year plans have almost always been wrong. I don't think there's anything wrong with planning for the future, even if I had been wrong. Here's what I've learned about those plans. They were usually myopically focused on my career and the job I held at the time.
I made my first five year plan when I was an equities trader. The plans were something like: (1) make six figures by year 2 of trading; and (2) by year 5, make a lot more, plus have a team of trainees. Not bad goals, but not particularly specific. By the early months of year 2 of trading, Lehman had blown up, and I was no where close to making six figures. I left that job, and six months later, found myself at an energy consultancy.
My next five year goals were similarly focused on my careers at hand, and were an extension of what I was doing at that time. They were something like become a "head of," with a team of direct reports who I would manage.
Fast forward today: I'm now enjoying a break between my last job and my upcoming job. During this time, I've decided to change my forward looking approach. Instead of making a five year plan, I'm taking a pseudo-retrospective view. I still have professional goals and plans, and they're in service of some specific, personal goals of mine.
Developing my personal goals: two letters and a plan
The other day, I wrote three different pieces:
A letter to my kids and grandkids, from the perspective of a 100-year-old me;
A letter to myself, giving advice to present day Tim from a 20-year-older Tim; and
A "what if" plan of action, presuming I had only two years left to live.
My 100-year-old self focused a lot on my family: my wife, my kids, my parents, and my siblings. He talked about his friends. In a word, he was about his relationships.
Twenty-year-older Tim focused on reducing worrying, and understanding what enough is. In a word, he emphasized mindfulness.
And end-of-life, young Tim, cared first about his family. And once he knew they would be taken care of after he was gone, he planned to spend every available moment with said family. He would stop watching TV, he'd stop reading and working out. He'd just have fun.
I suppose I could distill this all down into three words: relationships, mindfulness, and fun. Maybe what I want is to enjoy myself and be present with the people I love most.
Professional goals, redux
Going through those three letters after my initial drafts, I had to force myself to write about my career. I couldn't assume that finances would take care of themselves. Here's a snippet from my 100-year-old perspective:
Looking back on my life, I regret focusing too much on my career, worrying about how to "advance." What I should have realized, is that, by staying true to some of my other principles, professional success can happen without having to sacrifice my time with the people I love. Those other principles: do what you love, do it well. Work smart, learn effectively. Don't take shortcuts. Build relationships. Build trust.
And from my 20-year-older letter:
Know what enough is, stick to it, no more, no less. It will evolve, and that's okay. Don't get mad at yourself when you're above or below. You're going to regret working too hard or not having enough; that's just you. [...] So try to worry less about enough, and just spend more time with your kids and your wife and family.
What this exercise has reminded me is to keep a balanced portfolio, in a sense. It is my nature to "lower my shoulder" and go all in on my job. I know that I'll try to dive right into my next opportunity; I get psychic value from thinking, creating, and expressing, all things required in my next role. As trite as it may be, though, time is the only finite resource (or is it?), and I ought to check in every now and then and make sure that I'm also focusing on relationships, being present, and having fun.
Final words
I know I don't have "it" figured out. That's probably a new, or at least a more obvious, admission relative to past Tim when he was making his five-year plans. I'm still trying to suppress my tendency to focus narrowly on current emotions. I may not be detaching enough from current state and thinking. I suppose, though, that there's still some utility in at least having this "backwards" perspective on planning vs. the usual "forward" looking view.
Please read part II, which is about learning and finding the right job.
From the pros
This blog post was inspired in part by the Tim Ferriss podcast episode with Josh Waitzkin:
[...N]o one will know me better than myself 20 years from now. If my goal is unobstructed self-expression or self-actualization within an art, then the person who’s teaching me should be the person who knows me most deeply. And that’s my person 20 years from now.
The person 20 years from now is also a helpful visualization in being the person who would understand what my false constructs are today, and yesterday, and a year from now. It’s very easy to get stuck in the mindset, “I didn’t know before but I know it today.”
Perhaps time isn't finite. For a totally different read, check out Carlo Rovelli's The Order of Time.