Gambling on Myself

I’m not one who gambles. No judgement on anyone who does, in fact, most of my family really enjoys it.

I personally don’t go to the casinos or attend card games. I don’t play the slots when they’re available in establishments we frequent. I couldn’t even tell you when the last time was I played Lotteria. Most I do is play a couple of football squares from time to time, maybe several for Super Bowl, other than that, I prefer not to. There’s something about playing those odds, knowing the likelihood of me hitting a jackpot is slim to none. It makes me uncomfortable.


Recently, I took a huge gamble on myself — I launched my catering company! When I tell you I went back and forth for weeks considering the pros and cons, discussing it with my wife, thinking about all the ways it could fail and all the things which could go wrong, it was important I make a sound decision. Not just for me, but for my family. I mean, I worked in the industry for over a decade. I was part of the management team for one of the largest franchises in the business and oversaw the day-to-day operations. But… was I ready to roll the dice on myself?

I did it. I launched “Tommy Don’s” catering (a leg of “Tommy Don’s” restaurant) — it was terrifying but extremely rewarding. I advertised the launch, I created a more streamlined version of the menu, and I waited. My first order came in and it was sizable. My self confidence was telling me, “You can do this. You’re as prepared as you’ll ever be!”, but my anxiety was poking at me saying, “Stop while you’re ahead.” Well, I didn’t stop — I kept going. I cooked everything, packaged the order, delivered it and it was a hit! I received several compliments on how delicious and fresh everything was, including a call from a community VIP, and multiple leads for additional business. I feel proud — I worked hard and it was a win!

That’s not to say my first order didn’t come with lessons learned — of course, it did! Nothing major, no complaints from my customer, just administrative, in-house fine tuning on my end. There’s always a way to work smarter, not harder. I’m a firm believer in evolving, growing and getting things exactly right. I’m no stranger to hard work and I will continue my journey as an entrepreneur until I have secured generational wealth for my children.


The ultimate goal is to open my restaurant “Tommy Don’s”, however, the economy still isn’t stable enough for me to gamble on launching a new restaurant. In time, things will be on an uptick, and when it is right, I’ll secure a space and open doors to my restaurant. Until then, my catering company is a realistic and fully doable first step. I gambled on myself and I won. It feels really good!

I’m grateful to be where I am because I know that I am exactly where I need to be. I know that I can’t get where I want to be if I don’t first start moving. Baby steps lead to big moves. Big moves lead to more moves. I’m happy to be taking baby steps, because as long as I keep stepping, I’ll reach my destination. If I take no gamble, I win no reward.

I want to thank my family and friends for taking a gamble on me and my dream! Your support not only secured my LLC, but it also afforded me industrial pots, pans, utensils, cleaning supplies, delivery and catering items. All of which are required, none of which are inexpensive. It was scary to dip into it but this is what taking a gamble looks like. Thank you with all of my heart — I’m not going to let you down.


-Tommy Don