Playing offense is what I do. It’s part of my fabric as a human being. In this post, I’ll tell you exactly why Playing Offense is important. I’ll also explain how I’ve reaped the rewards in my life.

I used to work with a car dealer in Dallas, Texas and I’ll always remember a saying he had. Charles would say,

I want chalk on my toes…not on my heels

Chalk on my toes referred to being assertive and aggressive. He wanted to bring the fight, the energy, and to be in pursuit. Not the other way around. Having chalk on my heels meant we were receding, being pushed back, or operating defensively. It’s tough to drive forward from your heels.

Another quote I love and use quite frequently is from Amelia Earhart. The quote below adorned the side of her plane on her transatlantic flight.

Always think with your stick forward

The takeaway? Maintain your airspeed or crash. There is no option to pause. Stay in Forward Motion – – – – > at all times.

But let’s talk real life from yours truly. How have I been able to reap the rewards of Playing Offense? Below are four life examples of where I played offense and what outcomes transpired from the effort.

1. From Mower to Marketer: A 21 year old me with longer hair, and grass stained everything, worked for a mowing company. This company happened to mow the lawns at a local ad agency. Knowing I was destined to follow the advertising career path, one day I happened to run into the head of HR (Wendy) while trimming or mowing outside this business. I’ll never forget stating my intentions that day. I told her about my passion for advertising, and that if given the chance, I’d come back in a couple of weeks, cleaned up, nicely dressed and eager to discuss how I’d serve them as an (unpaid) intern that fall. That day I played offense. Nearly 11 years later in 2012 after progressing into numerous roles and transforming the business, I closed that terrific learning experience. It all started as an unpaid intern who played offense and took a break from cutting the grass to state his intentions.
2. Business Blind Spot 2012: I still have the email saved. It’s titled, “Opportunity Calls” and I sent it to a friend (Shout out Doug) on Feb. 27, 2012. We’d chatted from time to time, but this was an entirely new, and larger ask. I saw a large blind spot in the agency I was working at. The digital revolution was beginning to take shape, and we were caught on our heels, unequipped to serve the new media marketplace. A strategic acquisition with the right partner could change the trajectory of the business…and it did. The small digital shop where my friend was a partner, was acquired in the fall and we were off blazing a new trail forward. These are some of my most challenging, empowering, fun and fulfilling years of my career. In only a short couple years that felt like a sprint, we were a national approved digital vendor with some of the largest automotive brands in the business. I can’t take credit for the entire fire, but I know who struck the match 😉. It all started with identifying a need and stating opportunity.
3. Banker = Relationship Builder: In my early 30’s I started looking for answers to the question. I asked myself, “what do wealthy people do?” More specifically, “what do they own?” The answer I came across was ubiquitous…Real Estate. But I didn’t own any, nor did I know how to buy it or invest in it. I needed to close the knowledge gap. I reached out to my banker and asked for a lunch meeting. Specifically I said, “Look, I’m on a path to build wealth. I’d love to be more active in real estate. I need a mentor or guide. You happen to be a banker and quite likely know a person or two you could introduce me to.” I stated my intentions. I reached out. I made the ask. I benefited greatly. I met a new friend, was shown the ropes, and now have numerous relationships being built in the space. If I don’t play offense, none of this happens
4. Career Moves A little over four years ago I was burned out and frustrated with my current role as President of a media company. I needed a change to get my mojo back and I needed to feel good in my gut about my next move. So I started conversations with an old business partner I’d worked with. I reached out to the President cold and let them know what I was thinking. Although not overnight, the outreach, the ask, the intentions I laid out were clear. Three years later my life, my family, and my path all benefited from playing offense back in 2021.

If ever I find myself in a pattern of stagnation or boredom, I usually ask myself, “where do I need to play offense?” What effort can I uniquely control to move my life forward toward what I’m looking for? Therein lies the answer.

In each of the four examples noted above, I faced discomfort and future uncertainty at play. But guess what? That same discomfort lives in those unwilling to try, or unwilling to take a chance. So why not give it a go?

Newton’s Law of Motion

An object at rest remains at rest, and an object in motion remains in motion at constant speed and in a straight line unless acted on by an unbalanced force.