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It’s officially been two years since Digital Pudding became a thing. In that time, so much has changed. The industry has changed. Our outlook and philosophies have changed. I’ve changed. Even the circumstances resulting in the founding of Digital Pudding have changed.

It’s getting difficult to remember what life was like back then, which I guess is a good thing as we experience more success. The struggle of creating something from nothing, pouring countless hours and tireless effort into a fledgling digital marketing agency, unsure what’s going to happen next. I don’t miss those days. These days are much better. And we’re proud to have made it to two years old.

There’s something that’s been nagging me, though. What if I didn’t? What if I never jumped? Or if I never learned from my mistakes and poured that knowledge into a different type of digital agency?

It’s impossible to rewrite history like that. Yet I’m a fan of thought exercises. So let’s think. How would life be different if I didn’t take the road less traveled and stayed the course?

A Snapshot of Life Two Years Ago

By some measures, I was already successful before Digital Pudding started. In five years, I had risen from copywriter to vice president of a local mid-sized ad agency, building their digital marketing division from scratch.

At the same time, I hated my life. The constant churn of clients was too much. I increasingly found myself at odds with upper management on strategic decisions. Plus, employee turnover was high, as it often is in this industry, thanks mostly to the demanding schedule and thankless work on behalf of the clients. The average life span of a career there was shy of two years. I had doubled that and then some.

There was also a calcification of skills at play. Every client got the same program. Branding. Website. AdWords. Facebook.  Rinse and repeat. Doing the same thing over and over again with little intrigue for the same kinds of clients wasn’t going to propel my career. In fact, it could have the opposite effect.

Yet I knew there would be a possible payoff coming. The business had recently been sold. Its founder was now a common, well-paid staff member and figurehead. He wasn’t long for the job. At the same time, I was closing in on five years at the company, one of the longest tenured client-facing employees there. Five years would have been enough time to make a legitimate case I deserved to rise even further, becoming the face of the business after the founder’s retirement.

Yet, knowing what the business did, how they charged, how unsatisfied many of my clients were with my bosses, would I really want that responsibility?  Would I want that reputation? Would it be worth it?

I left my job there, mere months away from reaching that half-decade milestone. That’s where we pick up the story.

What Could Have Happened Next

There’s every reason to believe that I’d have gotten that promotion, it was just going to be a while. Five years wouldn’t have been enough. My old boss stuck around until a few months before this writing. It would have been a long, painful slog to get that brass ring.

For the sake of argument, let’s say it did happen eventually. I would have continued to hate my job. Upper management (the new one) was clear about the direction of the company at the time. We were in the business of churn for high-dollar clients running three to six-month campaigns with little service and lots of excuses. It was painful and arguably unethical. If you know anything about Digital Pudding, that’s not something I want to do.

There’s also a good chance my career would have stalled entirely. I was already concerned about skill calcification. At a certain point in this industry, you become defined less by your potential and more by your experience and connections. My experience was ripping people off. My clients would part ways without recommending my services. I could have ended up on a professional island, unsure of what would come next, eternally searching for clients to fuel the business for a little bit, until they cashed out.

Perhaps more importantly, I’d end up responsible for destruction. Dozens of companies came to my old employer as a last resort, the lottery ticket that had to pay off in order to keep the lights on. We were so confident we could turn businesses around, yet rarely did. The lawsuits from past clients. The bills never paid. That will wear on your psyche. How could I sleep with myself at night?

Keep in mind, this is the best-case scenario. I could also have reached the top of that organization, unable to move further. As the landscape changed around me, I’d still be there, VP of Digital Marketing, managing a rotating cast of characters, spinning my wheels for clients who wouldn’t be around long enough to see their payday. That slow death of a thousand cuts would be even worse. Even if things worked out, though, life would undoubtedly be grim. And so, here we are.

We’re Better Off in the Kitchen

If this exercise has shown me anything, it’s that you make your own future. When the chance came to start this business, I took it with a plan in place. I’ve stuck to that plan, exploring new avenues and angles as they arise. Some work out. Some don’t. You just have to set your mind to a goal and get out there and get to work.

I could have waited. I could have passed up the opportunity to start this company and made the best of the status quo. It might have worked out. It might not have. Either way, that’s not what happened. What happened is far better than what could have happened, because it’s real. It’s the world we live in and the one we need to improve. This ain’t Schrodinger’s Cat.

We can’t go back. Time marches forward. The decisions we made in the past will continue to have far reaching effects well into the future. I’d like to believe that my decision to enter a crowded marketplace of digital marketing consultants and agencies has brightened some lives, generated some results and made the world a bit of a better place. That’s two years in. Let’s see what the next twenty bring.

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