Find your obstacle today
I meet hundreds of business leaders every year. Many are smart, competent, ethical people.
Most, however, get stuck in the middle of our industry—never doing so poorly that they fail, but never achieving true financial independence for themselves or their team members.
Less than 10% of the people and companies in our industry achieve most of the success. And it’s not just about money. In fact, money is the result. These high achievers make a larger impact on the world. They help more people and help people more deeply. They touch more lives, inspire more hope, and receive the same in return.
So, what separates these two groups of people?
The average and those who achieve and inspire greatness? What makes you great?
I have studied this question for more than 30 years. To me, it’s a mural that I continue to fill in, piece by piece, and share with anyone willing to listen. Today, I want to share one common attribute that greatness seems to possess.
I believe obstacles play a huge role in making us great.
I think about this from two perspectives.
First, when faced with a major life or business obstacle, you are forced to make a choice. You must decide how much you truly believe in yourself and others. When faced with a real crisis, will you finally shed what is urgent and focus on what is important? Or will you continue doing more of what got you there in the first place?
Second, many times it takes an obstacle to move us outside our comfort zone and into action. You’ve heard me talk about mediocrity over the years. The absence of obstacles is often what creates the quagmire of mediocrity. Sometimes we need a push.
What happens if obstacles don’t present themselves?
More on that in a moment.
My first sales job out of college was selling copiers. After training, I was assigned a territory. During my first few months, I had some beginner’s luck and closed a few deals. The problem was that I was doing everything wrong—cutting corners, avoiding prospecting calls, failing to follow up. You name it, I was doing it.
Then my luck ran out.
I sold nothing for several months.
My stress level was off the charts. It wasn’t just the possibility of losing my job. I began to wonder if my sales career would be over before it even started. Then what would I do? As a 22-year-old kid, this was terrifying.
I fell into what I would today call a sales depression.
I lived at home, and my parents could see the state I was in. I would do almost anything to avoid picking up the phone. When I was out knocking on doors, I would sometimes have to take naps in my car just to find the energy to keep going.
It was bad.
One day, my dad sat me down and said, “Son, I didn’t send you to college for four years to have a job that makes you nauseous. Just quit and find something else. It’s okay.”
I replied, “Dad, it’s not that easy. If I admit defeat here and the next job doesn’t work out, then I have to admit it’s me and not the job.”
He looked at me and said, “Then I’d set my alarm an hour earlier tomorrow and get to work.”
Work I did.
I muscled through my reluctance. I worked longer hours. I attacked the job.
A few months later, I won Salesman of the Quarter. I was the first rookie in company history to win the award.
I was off to the races.
Earlier, I said that obstacles are a necessity for success.
But what if you’re not lucky enough to be presented with a do-or-die situation? Are you destined to wallow in the quagmire of mediocrity?
Statistically, many people do.
But it’s still up to you.
If obstacles don’t find you, you have to find them.
The best way to do this is to change your perception of where you are. The moment you believe something more is possible, your current situation begins to feel less acceptable. What once felt comfortable starts to feel limiting.
Unfortunately, what I’ve seen over the years is that many people wait for life to force the issue. It takes losing their largest client, a major business setback, or a personal crisis to create the urgency needed for change.
The most successful people don’t wait.
They create the obstacle before life creates it for them.
They challenge themselves. They raise the standard. They pursue goals that stretch them beyond their comfort zone.
Obstacles are not the enemy of greatness.
They are the pathway to it.
Find your obstacle today.
Related: Top MSP challenges for 2026: Talent, AI, security and scaling
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