The Five Year Plan

Five years seems like a magical number for some reason. A quick search on Google for “Five Year Plan” turns up an astounding 201,000,000 results.

As I have gotten older, I look at time differently. The impatience of a younger me (where six months or even two years seemed like an eternity) has faded away, and has been replaced by a me who asks myself what I wish I had done five years ago and what I think my future self in five years will wish for.

Almost certainly we all look back at some decisions with regret. I should have bought more $APPL stock! I definitely should not have worn parachute pants!

Of course, we also hopefully look back at some decisions with pride. I am really glad I agreed to that couples dinner where I met one of my now closest friends. I am really glad I bought that painting by an artist who is now well known. I am super happy that I downsized my living situation as it’s allowed me to remember what is really important in life.

Although I can’t predict the future (like they did about the flying cars of the future), here are a few things that I am certain nobody will ever look back and wish they could have done:

  • Nobody wishes they had bought more stuff.
  • Nobody wishes they had made fewer friends.
  • Nobody wishes they had been meaner.
  • Nobody wishes they had more hangovers.
  • Nobody wishes they had lost more loved ones.

Those are personal and individual thoughts and regrets, but what about larger community regrets and wishes?

As part of the growing Dallas startup community, I wonder in five years what we will look back on with regret and what we will look back on with pride. If we know what we might collectively look back on with regret and pride, couldn’t we change our behavior now to pursue that path?

Don’t get me wrong, some people are doing exactly that. This is not a call out suggesting that anybody isn’t doing anything, simply the wandering mind wondering if we are pursuing any paths that are great or bad.

So here is the list that I think my future self will look back on regarding five year wishes for the Dallas startup community:

  • I wish that we had done more to support awareness and spotlighting of companies that are not part of one of the two primary local accelerators.
  • I wish that we had been more selective about cheering on local startups and had cheered based on revenues and user growth instead of good PR.
  • I wish that the people we hold up as gurus and experts had been better vetted so we didn’t have to find new ones every few years.
  • I wish that the many local wealthy individuals and family offices in DFW had seen more solid financial results from the startup community.
  • I wish that investing in Dallas meant investing in startups that are actually headquartered here, not just that they were willing to drive here for an accelerator program.
  • I wish that none of the startups that were being held up as icons of startupness (yes i made that word up) in 2015 had vanished & bankrupted.
  • I wish that fewer local startups had to go West to raise money and find talent.

I am not suggesting that we as a community aren’t doing what is necessary to grow. Every week I am genuinely surprised at how much things have changed. Where there was once a barren wasteland, there are now regular community get togethers. Where there was once a complete absence of press about local startups there are now regular features in the local press.

We are making progress and some wonderful people are doing some wonderful things, but I hope that the older, more mature Dallas startup community will be able to look back in five years with great pride, few regrets and a big portfolio of successful companies to point at.


(Editor’s note: republished and edited with permission. The original post is here.)

Arlo Gilbert

#Inventor #Investor #Founder #Hustler #Husband #Dad - Voted most likely to find a loophole - Advising startups & running