It’s OK to Cry

John Jackovin
4 min readSep 21, 2014

An emotional week 10 culminates on my plane ride home.

I could write about a lot of things this week. I could write about the trip I took to San Francisco. I could write about the awesome meeting I had with this really inspirational connector/investor from the valley. I could write about how awesome it was to spend a day in San Franciso with the Dwolla team. I could write about a fantastic meeting I had with one of the largest retailers on the planet. I could write about all of those things, but I won’t.

This week, as week 10 of Techstars comes to a close, I am going to write about something totally off topic. I am going to write about an overwhelming feeling I had as I was flying home from San Francisco to Denver.

Winnie the Pooh Movie Trailer 2010

So I am sitting on the plane and I have my music on shuffle. On comes this music from Keane. I first remember hearing this music in the movie theater with Melissa and the girls. I have no idea what children's movie we went to, but this trailer for Winnie the Pooh was shown and it stuck out in my mind, so much so that I tracked the song down and bought it.

Four years later the music comes on and it totally reminds me of the girls, so I open my photo library, which goes back to 2008, and start flipping through pictures of the girls when they were younger. I couldn’t have been more than 3 or 4 pictures in and tears started rolling down my cheeks. I felt a bit foolish sitting on a plane, looking at my phone, wiping away tears.

Since then I have been asking myself why I reacted that way. Truth be told I am a pretty emotional person, but I don’t think I have a fully formed answer. I think it might be many factors converging at a particular point in my life. The first being that I have been away, with the exception of 8 days, for the past 10 weeks from the people I love the most in this world. That has been really difficult for me. I miss them greatly.

I was also coming back from a business trip, but I wasn’t going home. This typically doesn’t happen. Typically once you get home…you are home. I wasn’t. I didn’t get to see my girls. It also hit me how much the girls have grown up over the past 6 years. I miss those times when they were little and needed me. They are now 11 and 9 and getting to that age where they simply don’t rely on their dad as much.

I also think that there is a certain level of stress that I am placing on myself as we get ever closer to demo day to make this time away from my family really count. I mean, think of the worst case scenario, I spend 13 weeks away from my family and come back no better than when I left. Now, we are coming back unequivocally better off than when we left; I am certain of that. But it is a lot of pressure and the last 3 weeks are the most pressure-packed of this entire time. Still a lot of work to be done.

So I digress. As I was sitting there with tears streaming down my face I found it interesting that I was also laughing while looking through these photos. For example, the title picture made me laugh quite a bit. I am certain that almost no one else will laugh at it, but I can just imagine what Emma is thinking in that pic.

If you laugh, you think, and you cry, that’s a full day. That’s a heck of a day. You do that seven days a week, you’re going to have something special.

So as I sit here writing this post, it reminds me of a quote from Jim Valvano, “If you laugh, you think, and you cry, that’s a full day. That’s a heck of a day. You do that seven days a week, you’re going to have something special.”

In that moment I did all three and I am grateful that I did.

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John Jackovin

Building BREWD. Hawkeyes, Bears, Cubs...& Chicago. Love my 3 girls. Love technology and everything entrepreneurial. Love #CrossFit and good food.