About this article:
Dear Future Leader is a letter from a senior marketing leader to the next generation coming up in the most competitive, most automated landscape in the industry's history. The human skills worth building, the practices worth starting now, and the honest advice nobody gives from a stage.
Dear Future Leader,
I want to tell you something that took me a long time to actually believe, and it still catches people off guard when I say it out loud. Getting fired the third time was the best thing that ever happened to my career, not the first time, not the second, but the third, when I finally sat down and asked myself what was actually wrong with me instead of finding another reason to explain it away.
The answer turned out to be nothing. Each of those three jobs had looked like real progress while I was in them: more responsibility, bigger accounts, more trust every time, and each time I still ended up walking out the door anyway. For a long stretch I blamed the agencies, the chaos, the leadership, the culture, anything external I could point to instead of myself. Eventually I ran out of things to blame and had to look honestly at what I had actually been building underneath those firings, because there were three educations buried inside those three exits. I kept getting better at the work itself the whole time, even while the outcome kept saying otherwise, which is the part nobody tells you when you're the one packing up a desk. Getting fired does not automatically mean you are behind. Sometimes it means you are early, and nobody around you is positioned to see it yet.
Here is what I actually figured out, sitting in a townhouse I had just bought and could barely afford, watching the mortgage get closer with no job attached to cover it. I knew what those agencies charged their clients, because I had been the one running the accounts, and I knew the work itself was never the hard part. No secret system, no proprietary platform, nothing standing between me and doing it myself except one thing: nobody outside those buildings knew I could. That is not a skills problem. That is a lead generation problem, and mistaking one for the other will cost you years. A skills problem means something is wrong with you. An exposure problem means something is wrong with your visibility.
So in 2017, with about a month of runway an old employer had given me on the way out, I started making calls, not to clients, but to other agencies, people I had known for years mostly on the vendor side and had never once approached as anything other than a peer. I called Jim Licko, a partner at Ground Floor Media, someone I had stayed in touch with the ordinary way, the occasional lunch, a real catch-up now and then, nothing transactional about any of it. I did not pitch him. I told him I was going out on my own and asked what he was actually seeing in the market and whether there was room for us to collaborate.
There was. Analytics and attribution work was heating up that year, agencies needed real tagging infrastructure and actual process instead of duct tape, and it happened to be exactly what I did well. Jim saw the fit almost immediately, and Laura Love, who cofounded the firm with Ramona Robinson, backed it without much hesitation. Within a short window, I had real client work, from people who already trusted me before I ever needed anything from them, which is a very different starting point than cold outreach ever gives you.
What I did not expect was how much that one relationship would end up shaping more than just that first project. Ground Floor Media ran on relationship first, trust built over years instead of pure performance metrics, and watching them build a real business on that model is a big part of why Session Interactive is staffed the way it is today. That relationship did not just get me back on my feet. It changed how I think about building companies altogether.
None of this is timeless advice for its own sake. AI can already build the report, write the deck, and execute the campaign faster than anyone could ten years ago. What it cannot do is be trusted by another person who has watched you follow through, year after year. That is not something you can prompt into existence, and it is exactly what's left standing once the technical work gets cheap.
So here is my actual advice, and I mean it as an instruction rather than encouragement. Take the meeting, take the lunch, take the happy hour and the coffee and the 10-minute catch-up you think you do not have time for right now, not because it pays off on any predictable schedule, but because reputation is genuinely all you have in this industry, and people remember it, the good version and the bad one, for far longer than you would expect.
I have had people reach out 10 years after we worked together simply because they remembered how I showed up at the time, not what I actually built, and that kind of thing does not happen by luck. It is the only asset available to you that compounds before you have anything else to offer.
Being fired does not mean you are not good enough. It means almost nobody outside one building knows what you are capable of yet. That is a different problem, and it has a different fix. Start now, before you need it.
-Tyler, CEO @ Session Interactive