Reflections of a CEO: Learning From Your Mistakes

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“Ring the bells that still can ring

Forget your perfect offering

There is a crack in everything

That's how the light gets in.”

― Leonard Cohen


A wonderful and enlightening thought from the late great Leonard Cohen that shows us how during the pursuit of perfection we can actually find and see what’s more important.  Perfection is unattainable, so even the most organized, Type A people make mistakes.. Don’t let it define you. What should define you, instead, is the ability to recognize those mistakes and learn from them, and let it guide your path to something greater. 

I’ve certainly made my fair share of mistakes over the years, but I’d like to believe that I’ve used those moments as an opportunity to improve as both a leader and a person. By sharing a mistake I’ve made in the past, I hope that can also help shed light on the reality of navigating challenges and, in turn, finding even greater success and happiness. 

When I first became the CEO of Overskies, I (obviously) wanted to take the company to new heights. So, one thing that I strongly advocated for was increasing our agency’s service offerings. To me, it made sense to open up new business pipelines, thus reaching new customers in the process. We were gonna go places!

But, while expanding into new markets isn’t inherently a bad idea and can actually be a smart move for some companies, I quickly realized it wasn’t working for us. In my effort to bring in more customers, to evolve as an agency into something new, we weren’t really providing an A+ offering to our clients, existing or new. We also weren’t enjoying our work as much as we had in the past, which affects morale and culture, on top of the actual work we produced. Essentially, we were trying to be everything to everyone and failing. 

It was frustrating, no doubt.

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Still, we were able to overcome the issue by looking for the light in the cracks. We decided to be true to ourselves, to evolve in areas that were true compliments to what we are good at, and what we love doing. My team and I took a step back and took a deep breath and honestly assessed where we wanted to be in 5 years as an agency. What would the company look like? What types of clients would we have? How could we increase margins while still doing the work we enjoyed? After a thorough assessment, we put our efforts into more intensive training in these areas, with the goal being to deliver our absolute best where it counted most. In the process, we were also able to learn new things, give our work a refresh, and keep the ideas flowing (the power of teamwork!! And keeping things simple).

When the hurdle was finally behind us, we were seeing even greater success than before, and let me tell you - I did NOT think that would be the case in the thick of it. Most importantly, though, the team was so much happier doing what they loved rather than chasing work that was outside of their wheelhouse. I hope you can tell from my LinkedIn: my team means a lot to me, so this was huge.

I learned a LOT from the experience: it occurred to me that running a mature and successful agency is much like how we grow and change as individuals. I often see it when people in my life grow older: they become more secure in who they are and adopt a “take it or leave it” attitude. At Overskies, we have become much the same: we’re so good at what we do and are so happy to do it for the clients that see the value in it, and value what we offer. The transaction must be mutually beneficial, and that’s what we’ve been focusing on ever since.

So, my advice is simple: you cannot be everything to everybody, but if you chase excellence in the areas where you are already shining, and become the best version of yourself that you can be, you’ll let a lot of light in. This will be more than enough for your team, and for you as well. Keep that in mind and stop trying to force all your square pegs into round holes. 

Of course, there are other challenges you will have to overcome, and sometimes you might make a mistake. It’s okay! Just remember those wise words from Hannah Montana…


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