Investing (your life) in a startup

the future

Fast-forward into the future

I was drinking coffee with a good friend a few nights ago.

We were talking about everything from girlfriends to traveling to real estate to regrets. The one topic we kept getting stuck on was plans for the future. Would you fast-forward your life by 5 years to see what future awaited you? I imagine the allure of doing this diminishes as you get older. You doubt much will really change, so why waste 5 years?

When you're in your 20s, and have no idea what you're doing with your life, the desire to fast-forward is a bit more attractive. In particular, I'd love to see what my career looks like in 5 years. This is where the most uncertainty resides for me, so it'd be pretty cool if time could fly by and clean things up.

For example, I wish there was a clear path to career success. Where do I need to go? What companies should I work for? What do I need to do to be a success? It would be nice if a straight path was laid out in front of me.

Unfortunately (or fortunately), we can't fast-forward. But, we can do things to make us more likely to be happy with our outcome. I thought I'd share some of my tactics.

Reduce the chance of regret

You're going to regret not pursuing your passion.

For me, that's working in startups. I knew I'd hate myself if I never moved to San Francisco, so I'm taking the leap. I bought a one-way ticket to work at a startup out there. Your passion probably looks different than mine. It could be coaching a high school basketball team, designing t-shirts, or making music. What's keeping you from doing it?

You'll be happier with your future if you do the thing you love; not if you find an excuse to put it off.

Stack the odds in your favor

You have no idea if the decision you make today will bring you the outcome you want tomorrow.

It sucks, but it's true. Over-analyzing every decision won't help. Instead, focus on removing uncertainty. You might not land in the exact spot where you envision yourself, but you'll find yourself in the vicinity.

You want to get into Venture Capital, and you think your best route to that is working in a Business Development position at a hot startup? Cool, but don't miss the opportunity because you're afraid of not finding the perfect company. A perfect company doesn't exist. Stack the odds in your favor. Find a company with a few great characteristics and take the leap.

Every moment spent hesitating is wasted. Take one step closer to what you're being drawn towards. Your chances of success will be higher than if you remain stuck somewhere that you're not fulfilled.

Surround yourself with awesomeness

You're going to make a few terrible decisions.

They don't have to be the end of the world. As long as you surround yourself with awesome people, you'll be okay.

The startup you chose to work for is a flop and goes out of business 6 months after you started? That's terrible news. But, if you spent those 6 months building relationships with good people, it wasn't a waste.

The only waste is if you can't enjoy the present because you're so concerned with what's waiting for your in the future.

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