A celebration of the meandering path less traveled

This month marks the 13th anniversary of the company’s founding. On Leff’s 11th anniversary, a friend responded to one of those LinkedIn autogenerated prompts to send congratulations by saying, “I would have bet the under.” He’s not alone.

It was not a straightforward path here. I’ve had three separate careers since college: bartender, musician, and roles in business publishing. The first two might seem completely divorced from the last one, but the progression makes sense—in the rearview mirror, anyway.

Can we get another round of kamikazes down here?*

After graduating with a history degree (loved it; not recommended for employability), I bartended for four years in Lawrence, Kansas. I took the day shifts so I could play music at night, and though I didn’t realize it at the time, I picked up two critical skills: listening and client service. On the first count, I learned to ask questions sparingly and then sit back and listen to the regulars jaw in between gulps. The best bartenders aren’t the main attraction; they’re more like producers, setting the stage so everyone else has a good time. On the second count, I quickly figured out that providing personalized service and making people feel seen would lead to a tip and repeat business. So when Jim Hogan rolled up at 5:05 from his job managing Radio Shack, did I have a 32 oz schooner of Bud Light in front of an open barstool for him? You’re goddam right I did.

Do you take requests?**

Once I moved to Chicago, I threw myself into music full force while working more customer service jobs. Music was my passion and an amazing training ground for a whole set of skills. How do you attract good musicians? You gotta have gigs lined up. To do that, you have to put together a demo tape and press kit, drop them off at a bunch of clubs, try to get to know the booker or manager, and then call them on a regular basis until you get a date. I remember keeping a notebook with a list of the managers and when to call them next. If you got into certain clubs, you could work your way up the ladder bit by bit. It was all about relationships. The parallels to business are eerie.

Maybe most important, I learned a lot trying to corral passionate, creative people and mobilize them around a vision. I felt my way through these tasks and failed a lot. But when you’re completely committed, sheer force of will can often compensate for other shortcomings. I learned to write songs for our band with a specific audience in mind. I figured out how to put a good set list together. I dealt with musicians from backgrounds far different than my own. And I played all over the city—South Side, West Side, dive bars, a few of the top rooms in town.

Every gig offered a new experience, like Mother’s Day at the 290 Sport and Juice Bar (just south of the expressway near Homan Ave.), where an older woman asked me to dance and gave me an impromptu steppin’ lesson. (I failed spectacularly.) Nothing will equal it for me. Best job ever. When I miss it too much, I just listen for the constant ringing in my ears.

Music also teaches some intangibles that have nothing to do with musicianship. You have to be on time. You have to be a good teammate. You have to organize yourself. (Where’s the gig? What tunes are we going to play? Will we have a rehearsal? How much does it pay? What’s the dress code?) But most of all, you have to be ready to hustle. Because if you aren’t, someone else is going to take your gig. And who knows what opportunities will come from it?

Do you know ‘Donna Lee’?***

Music ultimately got me on my current path. I did a two-day temp job in the McKinsey mailroom that turned into other administrative jobs. Stuart Flack, the then-publisher of the McKinsey Quarterly, was also a guitar player, and we started getting together after work to play jazz standards. When I asked him if he had any advice for someone who wanted to get into business writing, he offered me an editorial associate position. I had no experience, but he later told me that he figured if I could manage a band, I could do the job. Eternal thanks to the gods of music for that one.


In our office, we have a bar cart that I pass on the way to change albums on our turntable. Having music playing all day doesn’t just drown out any pesky inner monologue that might get in the way of thinking; it also reminds me to heed the lessons I learned and apply them. Listen. Read the room. Be a good leader. Communicate. And hustle—every day.

Oh, and the next time you run into a Starbucks barista, a singer fronting a bar band, or a good bartender, think about hiring them. It might end up being one of the best decisions you make.


*At my first bartending job, the kamikaze recipe was three parts vodka, one part triple sec, and one part Rose’s lime juice. I remember using a funnel to mix them in an empty fifth bottle, if that tells you where mixology was in the early 1990s.

**Here’s the truth: once you take the first request, the floodgates open, and you can lose control of the crowd fast. Someone once asked me if the band would play a Brad Paisley song for $20. I told him we wouldn’t play a Brad Paisley tune for $20,000.

***I’ve been working for the better part of three decades to play the head to this legendary Charlie Parker tune passably. It must play well on alto sax, but if you’re a guitar player, you’d be better off banging your head against the wall for five minutes and then throwing your instrument out the window.

Scott Leff

Scott is the founder of LEFF. He’s spent his career helping executives and subject matter experts tell their story in a compelling way. In the process, he’s had the opportunity to work with C-suite executives, politicians, academics, and Olympians, not to mention dozens of talented writers, editors, and designers in the business world. Scott developed the concept of “lean content creation” as a cost-effective way to support comprehensive, integrated communication strategies.

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