If I Were to Do it Again…

I’m nowhere near the age of retirement.

In fact, I’m not sure I actually believe in the concept of retirement. Yet, for some reason, a key line of thought this year has been “What would I do if I were to do it again?”

I decided to take a crack at writing my thoughts on starting over. I’m hoping it can help 1) inform future decisions, and 2) maybe, perhaps create value for younger people.

If I were to start over again with – somehow – the knowledge I have today, I would focus on:

1) Building Resilience

Growing up, we all face adversity.

Adversity builds character and resilience, yet in spite of facing challenging situations, we rarely have to deal with prolonged stretches of adversity; the kinds of adversity that force us to dig deep, embrace change, and build a greater level of resilience.

Having experienced near constant challenges this past year, I find it strengthened my confidence and the trust I have in my abilities.

So… if I were to do it again, I would make sure to push a project – say Flagback – way past the line where conventional wisdom (and probably everyone around me) would have told me to quit.

Win or lose, resilience is worth more than the $20 to $40k I could have lost keeping the business going an extra year.

Money comes and goes, but resilience is forever.

2) Increasing Learning Velocity

Although today I make significant investments in learning and I’m very mindful of my learning velocity, things weren’t always like that.

Maybe because I had just spent 17 years in school, or because I felt school was the way to learn, I feel like I slacked off in my early 20s.

If I were to do it again, I would focus on maximizing learning velocity right out the gate. This could mean:

  • (Intentionally) Working in smaller organizations;
  • Selecting jobs based on what I can learn from the direct manager;
  • Finding better mentors;
  • Spending more time challenging and debating;
  • Moving to a tech hub where there’s more (not less) competition for work;
  • Reading on a broader set of topics;
  • Getting out of my comfort zone as often as possible;
  • Spending time reflecting and dissecting learnings.

Better knowledge means better decision-making frameworks. I’m sure better frameworks would have helped prevent a costly mistake or two. :)

3) Things That Compound

Whether we’re the ones choosing how we allocate our time or not, time is always an investment. We can decide to invest in our work, our relationships, our leisure, our assets, anything really.

Given equal time each day, and the ability to start over, I would invest my time and energies in things that compound and have the potential to create outsized returns like…

  • Learning: See above ☝️;
  • Creating Content: (Quality) content compounds. It builds your brand, increases your visibility, and strengthens whatever positioning you have;
  • Building a Network: The more people you truly know, the more opportunities you get. Simple as that;
  • Building an Audience: Similar to building a network, the more people know you (or know of you), the more amplification you get on future projects;
  • Interests: Compounding interests create wealth in the long run. It’s not exciting, but it’s proven to work time and time again;
  • Real Estate: There’s many ways to monetize real estate, but the general idea is that the more properties you own, the more properties you can own (and monetize).

Compounding requires patience and dedication. It’s a perfect strategy when you’re starting out and have 40 years in front of you.

Would I Do it Again?

Unfortunately, I can’t go back to my early twenties (I wouldn’t want to actually), but I can factor in some of these truths to improve future decision-making.

No two people are given the exact same starting point and opportunities, and everyone has a different game plan.

The things I would have done differently might be what someone else was doing all along.

In hindsight, these 3 things would have simply improved my current game plan; a game plan I discovered at the cost of not doing the above strategies. Ironic… I guess.

© Photo by Hello Lightbulb