blogging – Grandpa Bob Encouraging Leadership

As a kid, September marked the end of summer’s glorious freedom and the start of another school year. Truth is, by mid-August, all the kids on my street were getting bored and restless, ready for something new.

My birthday is in September. But because it coincided with back-to-school season, my presents were school clothes. Useful, yes, but hardly the exciting stuff of childhood fantasies. My brother, whose birthday is also in September, was in the same boat—more school clothes. Still, it usually meant two cakes in one month, which always felt like a win.

Fast forward to adulthood. September takes on a new meaning, especially if you own or run a business. It’s the last month of the third quarter—the point where you should have a pretty good idea if your business is on track for the year. Strategic planning for next year is underway — the annual cycle never stops. Little time to pause and reflect. There’s always a new deadline, a new target. September is less about questions and more about answers and execution.

Then life throws in its own strange layers. In 2019, my father passed away on my birthday. A heavy twist of fate that turned my annual day of celebration into something far more complicated. In a strange twist of symmetry, last year, my mom died on my brother’s birthday.

Now, both of our birthdays are marked not just by the passage of time, but by the memories of losing our parents, their passing dates forever linked to our birth dates.

September marks the birth of my oldest son-in-law, my youngest daughter (32 years ago tomorrow), and one of our eight grandchildren (also tomorrow). Lots of celebrating and gift giving…and some ice cream, of course.

All of it adds up to a certain strangeness in September for me—a month of beginnings and of endings. A mix of personal milestones and bittersweet memories.

p/c – Blessing Ri on Unsplash

I’ve received (and read) lots of advice in my lifetime. I’ve even had an opportunity to give advice to others.

The most valuable piece of advice I’ve received was from my dear friend, Jay Scott, around 1991 or 1992 (paraphrasing):

“Mr. Dailey (we refer to each other formally, of course), everything in life comes down to writing a check. You want a new car? Write a check. You want to learn a new skill? Write a check. You want to add something nice to your house? Write a check. You’re either going to write the check or not. All the rest is just detail.”

When he said it, I didn’t think much of it. It sounded like a flippant observation that oversimplified life’s choices.

As I’ve lived my life and encountered tons of situations, opportunities, and decisions, I’ve come to realize the genius in his observation.

The check may be money…the literal meaning of the word “check.” Sometimes the check is the decision to invest something of your own personal value into an idea, an object, or a cause. The check becomes a commitment of your finite time and energy…and maybe your money.

The idea that all the rest is just detail reinforces the notion that while we may elaborate on our decisions with lengthy justifications or stories, at the core, it’s about that decisive moment of commitment.

I’ve found that most of the time I have my decision made about something within a minute of considering my alternatives (whatever they may be). Whether I act immediately on that decision (write the check) or wait some undetermined time period (sometimes years) is another matter.

I’ve applied this fundamental knowledge about humans and their check-writing decisions many times. If my boss says that he supports an idea or strategy, I try to get him to “write the check” about that support as quickly as possible. It’s easy to support an idea in the abstract or tell your employee that you support him or her. It’s something entirely different to then act on that support by “writing the check.”

If the boss (or anyone for that matter) talks about how they believe in something or they support something, if they’re not willing to write the check for it, you know they’re just telling a story. Only when they commit their check (money, time, reputation, etc.) to something are they truly supporting it. Another phrase, “having skin in the game” applies here. No skin in the game, no commitment.

It all comes down to writing the check.

p/c – Tommy Lisbin – Unsplash Why? This climber has written the check(s) and is fully committed to this task. And, the goal is in sight.