Nov 16, 2023
Business
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5
 min read

Developing a Long-Term Strategy

What do you want to do for the next 20 years? It's one of the best questions out there, but challenging to answer. The vast majority of people (me included) tend to flow through life making the best decisions they can. These decisions may connect to some longer-term strategy, but more likely they're just based on your feeling at that moment in time. There's nothing wrong with that - it's a bit of an adventure.

I've largely lived this way - taking jobs that were good opportunities. Even when I left the investing world to be an entrepreneur, it wasn't because of some grand vision. I just thought it was a great opportunity.

After we sold WeHero, my partner, Ben, and I were faced with the same question. What do we want to do for the next 20 years?

So what did we do?

Since we're complete nerds, we both built powerpoint decks focused on our life vision. This forced us to put our thoughts into writing. It then allowed us to push back and challenge things that weren't clear or didn't make sense. What did we include in these slide decks?

  1. What were our long-term goals for the next 15 years? This included net worth, income, vacation, and what job tasks we wanted to being doing every day.
  2. What is our current performance against our goals?
  3. How do we want to pursue this after we complete the integration and are no longer working for WizeHive?
  4. What are our outstanding questions and fears that we have?

Putting this together wasn't easy and required a few late night sessions supported by a bit of bourbon. However, after finishing it, I felt a sense of clarity. I knew where we're headed and how we can get there.

One of the best parts about putting together the deck was that I met with friends and advisors to get their feedback and thoughts on it. They were able to push me on my fears and help solidify some of the questions I have outstanding.

If you're thinking through something similar, I'd be more than happy to do this exercise with you.

Do I have all the answers? No! Will my life go exactly like this vision exercise? No! The best part about life is that you can continue to pivot and adjust your plan as you learn new things. I'm just excited to have a consistent plan that I'm working towards.

For the time being, I'm entering my season of productivity. It's time for me to get working towards these goals.....

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