My Unlikely Benefactor

This week marks 10 years since my first day working in Chicago.


I moved to the city in November 2006 with $2,000 to my name and no job. Impractical to say the least, and the exact opposite of the advice I’d give to, say, my little brother.


I spent the first few weeks sleeping on a mattress in the living room of a small one-bedroom apartment, somehow sharing that tiny space with two friends and a dog, and job-searching non-stop. We moved into a bigger place in December, but by the middle of January my financial reality became more and more clear. If I didn’t land a job within the next couple of days, I’d be down to my last dime and wouldn’t make the next month’s rent. I’d exhausted the connections my KC friends had helped me make, and was as discouraged and fearful as I’d ever been.

In the year-and-a-half leading up to my move, I’d worked for a small but respected ad agency in downtown Kansas City, the same company for which I’d interned the prior summer during college. As first jobs go, I couldn’t have asked for much more. It brought its share of expected, less-than-glamorous responsibilities, but I worked alongside extremely talented and down-to-earth people, and learned a ton about the ad world and business in general.


Our CEO and founder was a charismatic and passionate guy, focused on growing his business but also taking care of his people. I remember being impressed by the fact that he remembered my name after one brief introduction during my first week as an intern – a small but meaningful gesture to a 20-year-old kid just trying to get his career off the ground.

Nevertheless, by the spring of 2006 I’d made the decision to move to Chicago and submitted my resignation in September, grateful for the opportunity but beckoned by the bright lights of the big city at every turn.


My last few days brought the usual exchange of pleasantries and well-wishes among my colleagues. Our CEO said he was disappointed to see me go but wanted to do what he could to help me find a job, an offer I obviously welcomed but from which I didn’t expect much follow-through. After all, he was running his then 25-year-old company and I was another kid with big ambitions and little experience, a cliche I’m sure he’d come across hundreds of times before, and would hundreds more in the future.

Then in mid-January 2007, faced with the very real possibility of being forced to move back to KC after just three months, I finally “got a bite” through a local recruiter and after a series of interviews, received an offer with one of the premiere advertising agencies in the country, BBDO.


I’ve never felt such a combination of relief, joy, pride and excitement as I did in that moment.


I fumbled out some words of gratitude to my recruiter for all she’d done, then just before we hung up she asked something I’ll never forget:


“Did someone at your old job write a letter to BBDO’s President?”


Me: “I know my old CEO had said he wanted to help, but I really didn’t think much of it.”


Recruiter: “Well they got it, and it definitely helped set you apart.”


Not only had my CEO written a glowing letter of recommendation on my behalf, but he’d personally mailed a hard copy to the Presidents of every ad agency in Chicago that was a part of the “4 A’s,” an industry organization of which his company was also a member. That amounted to around 15 different company presidents, many of whom he’d never met.

I’ve thought a lot about what my takeaway from this memory would be. After all, a letter of recommendation isn’t exactly an uncommon thing. Referrals and endorsements today are so easily exchanged over LinkedIn and e-mail that they hardly seem as meaningful as they once did.


But sometimes a simple act of generosity completely changes the trajectory of someone’s life, and that was certainly the case for me. My CEO put his professional reputation at risk among the leaders of his industry, all for for a junior associate with whom he hadn’t even worked all that extensively.


10 years later, not only am I still plugging away in this crazy ad game, but that first job led to so many new relationships, learning opportunities and experiences that I’ll cherish forever…not to mention an eventual run-in with my now wife! It also instilled a sense of responsibility to deliver on the opportunity he helped uncover for me; to make the most of this gift and ensure its potential was fulfilled.

Sadly, my old company in KC closed its doors suddenly in 2011, its hundred-plus employees left to find work or start over altogether. I don’t know what the factors were surrounding its closing, but I can’t imagine how hard that must have been for my old CEO. Not only did that company represent the majority of his life’s work, but leaving his employees suddenly without work of their own must have been devastating.


I trust everyone has moved on now, fully immersed in new jobs, new challenges, passion projects, geographic moves, or retirement.


But I wonder about my old CEO.


I suspect he retired when the company closed, and I can’t help but wonder if he still wrestles with regret over it – What could have been? What might they have done differently? How might things be different today, with the company thriving and positioned for long-term success?


But those moments he might look back on with regret or the decisions he might second-guess, pale in comparison to the impact his gesture had on my life and, I suspect, similar gestures had on many other former employees over the life of his company. And I find that idea so important. It reaffirms for me that our own regrettable decisions don’t diminish the power of the positive impact we make on others. Because so often it’s the regret that feels more real; more tangible. It’s the disappointment that dominates our thoughts, makes us question ourselves, and poisons our self-confidence.


There won’t be any monuments built to commemorate my CEO’s old company. I suspect its old building was quickly filled up by a new tenant, the years of work represented on walls and in conference rooms swept aside for “the next big thing.”


But for my part, I like to think that knowing his letter kick-started what I had long-considered a dream (working for a big-time ad agency in downtown Chicago) might provide him with some degree of comfort. That understanding the difference he made on my life 10 years ago might be rewarding in some small way. Because our most concrete and long-standing legacy lives on through people, not buildings or balance sheets. And because of acts like my CEO’s back in the Fall of 2006, I like to believe that his legacy and that of his company lives on in people like me and in so many others who contributed their own small part to its history.

4 thoughts on “My Unlikely Benefactor

  1. Justin! I love this! What a cool story.☺So glad that things have worked out the way they did for you. As always…I am so proud of you!☺☺☺☺☺

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