Earlier this year, I got myself two coaches: • An AI coach I met with on Friday afternoons (Kevin Connor — awesome) • And a standup comedy coach whose class I joined on Monday nights (Carmen Vallone — also awesome).
The AI class made me a better CFO. But surprisingly, being a CFO made me better at standup. It turns out that writing a five-minute comedy set has a lot in common with building a business plan.
Listening & Learning
Both processes start with listening and learning.
In comedy class, you soak up insights from your coach, then test ideas on stage and off with your comedy buddies. You quickly learn what lands and what doesn’t.
It’s not so different from how a CFO works with the CEO and department heads — listening, testing ideas, and doubling down on what works. That cycle of learning and adjusting is at the core of every great business plan.
Tying It All Together
The art of business planning is in tying it all together — aligning every function around a central theme that unites and inspires.
A good standup set works the same way. It needs a through-line — a unifying theme.
Mine? “My last name, my marriage, and other things that are long and hard.”
So yeah… probably not the right material for this blog. Sorry.
Strategic Allocation of Resources
Comedy coaches preach the importance of an “economy of words.”
When you’ve only got five minutes, every word matters. Long setups mean fewer punchlines. You optimize for more laughs per minute by cutting the fluff.
It’s the same principle that CFOs use in financial planning — trim the nonessential so you can invest in what truly drives results.
Reacting to the Unplanned
In business — and in comedy — success often comes from how well you react to the unexpected.
CFOs use KPIs and reporting cadences to help leaders pivot quickly.
On stage, you plan your “tight five” but leave room for spontaneity. My biggest laugh at the grad show actually came from an unplanned moment — an audience member’s overly enthusiastic reaction to one of my off-color jokes. (Looking at you, Kim C. Shaw, MAML, RBLP-T)
My response to her reaction? Completely improvised — and it killed. Thanks, Kim.
The Payoff
The payoffs differ — business planning leads to happy financial statements or maybe an exciting letter of intent.
Comedy pays in belly laughs and applause.
But don’t underestimate that applause. If any of my clients are reading this — a round of applause every now and then would be nice. (That’s a joke.)
In both business and comedy, timing, truth, and connection matter most.
If You Enjoyed This Article
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About the Author
Phil Nahajewskiis a dynamic CFO known for helping companies scale with both financial smarts and heart. With experience spanning billion-dollar enterprises, scrappy startups, and nonprofits, he blends rock-solid financial expertise with a people-first leadership style.
Phil loves making the complex simple, whether it’s budgeting, systems, strategy, or inspiring teams to grow. He’s also the host of the Florida CFO Group Coffee Talk Podcast (Season 5 now streaming on LinkedIn, Spotify, Apple, and all major platforms), where he brings fresh conversations and a little fun to the world of finance and beyond.
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