The Wins That Come With Losing

By Todd Lilly, Senior Digital Producer

Losing. What defines loss? It can be as simple as the final score in the big game. In life, it isn’t so simple. In life, how you lose defines your character and, ultimately, how you win.

If I am honest with you, this isn’t the first draft of the article. I wanted to glaze over the loss I have suffered while giving a lot of anecdotes. I have lost and not a big game type of loss. For the past several years, I have been on the slow track of recovering from life loss. I lost a very successful business. I lost my home. I lost a marriage and then, I lost another one. Those are the losses you can see. The part that you can’t see is that I lost my confidence.

I have always been scrappy – chasing down opportunities has always felt natural to me. I have always tried to succeed and learn from others I admire. I honestly don’t remember a time when I wasn’t trying to take on the characteristics of those I respected. I also have had a very strong need to be rewarded and it started early.

I grew up in Houston, and I have always been hungry. When I was six, my mom loved to shop. We would go to the mall – frequently. The incentive to tag along without much push back was a stop at the mall’s Chick-Fil-A. Not only did the sandwiches stick with me physically, but they created a memorable childhood experience that I never forgot. I owed some degree of my current state of happiness to the Chick. During my Junior year of High School I decided to write a letter to Truett Cathy, founder of Chick-Fil-A. It was basically a love story from this chubby kid. Two weeks later, I got a personalized note from my hero inscribed in his autobiography entitled, It’s Easier to Win Than Fail.

My exchange with Mr. Cathy taught me several things.

— Gratitude. Expressing gratitude goes a long way with people. People deserve to be recognized for making above average efforts.

— Care. People making above average efforts take pride and care in what they do. Care makes experiences priceless.

— Thoughtfulness. It’s a byproduct of care. Being thoughtful means you are listening and paying attention. Thoughtfulness also leads to gratitude.

— Purpose. Mr. Cathy could have signed his book and sent it my way. That was more than expected, and more than enough. But, he took time to express care and gratitude by personalizing a note back to me.

— Taking action…and asking what you want. Without asking, or fearing rejection — this experience that happened almost 30 years ago never would have happened. And had it not, I wouldn’t be sharing it with you today.


I took those experiences and wove them into a business, literally. I started Fill In The Blankie in 2004. The idea was to peddle ultra personalized baby blankets online. Sounded easy enough, except I knew nothing about blankets, textiles, or e-commerce. How hard could it be? Thought I knew Google Adwords. I was wrong. When you have your own skin in the game — it has a tendency to make you care even more. It caused me to relearn what I thought I knew in very short order. With lots of hard work — it became a success, for a while.

Ultimately — it failed. Why?

Looking back, I couldn’t find a balance. I did a piss poor job of prioritizing and budgeting. I didn’t delegate enough and did everything myself – or so I thought (there may be some trust issues there). I didn’t trust those that I hired to care as much as I did. There was little to no self-control. On the outside, I was traveling to and living in picture perfect places. Nantucket, Rosemary Beach, Kessler Park. While on the inside, I was sinking deeper and trying to cover up my debts and decisions. I couldn’t care about others because I didn’t like myself, so I continued to hide behind a facade. I made lots of impulsive decisions. I found myself treating each symptom. I ignored the overall diagnosis continuing to live in denial — hoping it would all go away.

It is not easy to write this. That paragraph, getting it right and truthful, was difficult. It’s taken me six years to own my losses. But, owning it, and writing it, frees me from much of the heaviness. It does not fix all of the fallout associated with it. It does not help fix relationships lost. It doesn’t pay off debts. But, owning it is a hell of a lot better than hiding from it. It has created character and one that I respect.

I recently saw this TedTalk by Jia Jiang — 100 days of rejection. It’s life changing.

No — really. I mean it. This video will change your perspective and encourage you to try (and then try harder).

When you do — you’ll win some and you’ll lose some. But, you’ll learn from every single thing you try — regardless the outcome.


I tried things. I succeeded in some. I failed miserably at others. But, I’m wiser for it all. I now know better. I know my limits. I know when to ask for help.

Today marks my last day at Dieste. I’m on to my next chapter. I’ve made so many friends here. Friendships that I think (and hope) are lifelong friendships. That’s a win.

People at Dieste care. They are thoughtful. You can’t make it down the hallway without receiving a hug. People take time to thank people, genuinely. None of these should seem special or out of the ordinary — but, to me they are. It doesn’t happen everywhere — but, it does here. They all remind me of the lessons I took away from my exchange with Mr. Cathy 25 years ago.

During my time here at Dieste I have been able to take on new challenges and try new things. I’ve been able to spread my wings again. And for that I am eternally grateful. There’s still a long road ahead. Not just for me, but for each of us.


They say…

You can’t win if you don’t play.

They also say…

You can’t win if you’re afraid to lose.

I’d say…

— Chase your dreams, but do it responsibly.

— Know when to cut the cord on a bad idea. Own the mistake. Move along and try something else.

— Dare to play. And dare to lose. Because only then, can you truly dare big enough to win.

Hugs and adios for now,



Todd is an entrepreneur at heart, but an agency guy in mind, body, and spirit. He strives to deliver ideas that show care and drive results. “If we’re not having fun then we’re not doing something right.” Outside the office, Todd keeps busy with his two sons, Ethan and Noah, exploring the great outdoors and taking pics along the way.



Dieste Inc