Sometimes When You Lose, You Win (Part 3)

As entrepreneurs, we are out here grinding, chasing big dreams and trying to knock the cover off the ball. When the stakes are high, we all hope for the best and sometimes get attached to the outcomes we want. But when things don’t go as planned, we can get down on ourselves.

Don’t do it.

Why? Because I’ve learned an important lesson on this entrepreneurial journey: When things seem to not be going your way, they can take an unexpected turn that works out completely in your favor. In other words, sometimes when you think you lose, you ultimately win.

I’d like to share a quick story to make my point.


A Loss

In February 2016, Money Magazine flew me to Detroit for a photo shoot at my printer for a feature article that was supposed to appear in the print issue of the magazine in April (which goes on news stands the end of March). The April issue couldn’t come out fast enough for me because my business needed a PR jolt badly since I was trying to get out of the cash-flow hole from the Groupon deal I did in the fourth quarter of last year.

In early March, the magazine emailed to tell me the feature was being pushed back a month, to the May issue (which would go on news stands the end of April). While not the end of the world, I was bummed because, like Pookie from New Jack City, I needed that (PR) hit badly, yo!


A Win

A few weeks later the magazine emailed to tell me they wanted to shoot a video to go along with the online article and they were sending a videographer to my home. Seriously? Amazing.

The video they created allowed me to tell the story of the startup journey that I wanted to share for a long time, on a large media platform. So that was a HUGE win. And it wouldn’t have happened if the original publishing date for the story didn’t get pushed back.

Here’s the Money Magazine Video:



While “losing,” but actually “winning” doesn’t happen all the time, it does happen often enough that you should remember when things don’t go your way, don’t worry, because the “loss” could completely swing around in your favor and be something more awesome than you might have imagined.

Hang in there!

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  1. Great advice and you are so right you do win and lose some in what we do, but never give up as the best hopefully is yet to come!! 😉

  2. I feel like sometimes things happen for a reason, and losing one opportunity may open a door to something even better. That’s obviously not the same as this scenario but along the same lines. I’m with Janine…hopefully the best is yet to come!

    1. Yes. It is hard for us to have that perspective after a big disappointment, which is why I try not to get too attached to expectations of outcomes. I try to stay positive at the macro level, but neutral at the micro-or event specific-level. Otherwise, it’s too much of a mental and emotional rollercoaster.

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