By Chris Heivly, Managing Director at Build The Fort and Startup Community EIR @ Techstars

Simon Sinek has that amazing TEDx talk about “starting with why.” It is a fantastic way to craft a message around your business “why” instead of what or how. But what if you applied the same thinking to your work? I used to think the question was, “Will my mom or dad be proud of the work I’m doing?” That can easily be constrained to the what and the how in the Sinek filter.

Now I think the real question is, “Will they be proud of why I’m doing it?”

Because if you grew up like I did, your parents didn’t grade you on your business plan or even how much money you are going to make. They graded you on whether you were becoming the kind of person they’d trust with a neighbor’s spare key.

Here’s the story that still sticks with me.

When I was an impressionable 15-year-old, my father had a series of 3 minor heart attacks in 3 days at the age of 39. A quadruple bypass soon followed the next year. He never worked a day after. So our world did not revolve around business or work for many years. In fact, he never did quite understand about being a venture capitalist or starting up an accelerator business.

Questions were always about the people I was working with. Tell me more about company X and how you are helping them succeed. Never did I hear something like “Did you dominate?” “Did you crush it?” Just… did you treat people right?

My mom had her own version. She’d ask questions that sounded boring at the time but feel genius now: “Are people getting something out of your work?” “Are you being kind?” “Are you sleeping?” “Are you eating real food?” “Are you building a life that won’t fall apart the second something goes sideways?”

They weren’t anti-ambition. They just didn’t worship it. I feel like it's more about influence than ownership.

They cared about stability — not in a “play it safe” way, but in a “build a foundation” way. Pay your bills. Keep your word. Don’t turn into a different person when you’re stressed. Don’t step on people just because you’re in a hurry. And for the love of everything important, don’t confuse being busy with being valuable.

So when I ask myself if they’d be proud of my work, I run it through a scoreboard based on why, with a touch of how:

• Am I being decent when nobody’s watching?

• Am I treating people like humans, not transactions?

• Am I building something sustainable — or just running on adrenaline?

• Am I leaving the people around me better than I found them?

If the answer is yes, then I think my parents would nod, maybe smile a little, and say something like, “Good. Keep going.”

And honestly? That’s the kind of proud that lasts.

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