Recently, I spoke with Tim Fitzpatrick. If you don’t know Tim, he was working at the MSP that I bought into in 1996.
I met him on my first day, and that kicked off a thirty-year journey across three businesses: Dynamic Digital Services, TruMethods, and now Kaseya. It’s amazing how one conversation can transport you back through decades of memories.
We spent about 45 minutes reminiscing about the past. We laughed about so many funny situations along the way. We both commented on how lucky we feel for our careers.
I look back with such fondness and gratitude.
After we spoke, I picked up one of my journals from those early MSP days. I was struck by how many of the entries I shared were about how difficult things were in the moment.
Financial stress, people problems, and a few near-death experiences for the business.
I found entries where, early on, I questioned myself and wondered if I was good enough to see it through. The doubt was real, and it felt overwhelming at times.
I spent the rest of the evening thinking about the contrast between my conversation with Tim and my journal entries.
What I concluded was that success determines how we feel about the past.
The setbacks, the doubt, the frustrations fade, and all that’s left is a feeling of accomplishment.
I know people who went through the same struggles as I did back then and didn’t achieve the same level of success. They feel very differently about their careers. Their stories remind me how fragile confidence can be without wins to back it up.
Here’s my point: You may be going through a tough time in your business. Maybe you’ve been in business for several years or many years and never achieved your potential.
You might be questioning yourself right now.
I get it. I’ve been there. It just takes a little success to build on, then a little more to change your expectations, and six to twelve months later, you can be on a new path.
Maybe you need to increase your value and pricing to your current customers or add some new logo customers at the right price.
You might have trouble taking action in these areas.
Just approaching three customers to explain your new value and having one of them say yes is a win. That single yes changes everything — your mindset, your confidence, your momentum.
You can develop some COIs and get one good lead. Even if you don’t close it, you’ve changed your expectations.
Nothing succeeds like success.
So, here’s what I want to tell you. Whatever you may have experienced in business, if you can reach your goals, you will look back over all of it fondly. And here’s the best part: you get to keep that feeling for the rest of your life.
That conversation with Tim reminded me that the struggles we’re going through today will become the stories we laugh about tomorrow — if we just keep pushing forward.