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The Vantage Point

From "Can I Do It?" to "What Can I Do Next?"

The race that changed the question I asked myself, from can I do it to what can I do next, and what that shift means for building a business.

A practical business perspective from Vantage Point Risk.

There’s a big difference between participating and competing.

Both matter. Showing up is always better than standing on the sidelines. The person willing to enter the race deserves more respect than the person watching from the side and criticizing everyone else.

But competition does something participation alone doesn’t.

Competition changes you.

It forces you to face failure and defeat. It tests how you respond when effort isn’t enough. It teaches you how far you can push yourself, how deep you can go, and whether you’re willing to keep moving when your body and mind are both telling you to stop.

That can happen in a 100-meter sprint or a multi-day race. The event may last seconds, hours, or days, but the lesson is similar.

At some point, you have to endure.

And if you never learn how to endure, I’m not sure you ever really learn how to succeed.

I spent years competing in cycling. I raced road, cyclocross, mountain bike, endurance mountain bike, and endurance road events. I also promoted races across those disciplines and managed several cycling teams.

I still compete today, both running and riding.

The reasons are a little different now. It’s less about beating everyone around me and more about pushing myself. But I still approach it the same way.

I prepare. I set goals. I measure the result. I look at what went well, what didn’t, and what I need to change. I still want to get faster and better.

That mindset has shaped how I approach business, leadership, and difficult goals.

But one experience taught me more about it than anything else.

It was the Cascade Cream Puff 100.

My First Goal Was Just to Finish

I helped promote the Cascade Cream Puff for several years before I decided to race it myself.

The Cream Puff wasn’t a casual mountain bike ride. It was a 100-mile endurance mountain bike race with a huge amount of climbing, technical trails, and a long day on the bike.

My first attempt didn’t end with a finish.

I spent more than 15 hours on the bike, and it still wasn’t enough.

That’s a long time to work toward something and come up short.

The next year, I came back and finished in around 14 hours.

At that point, finishing was the goal.

The first year, I didn’t know whether I could complete the event. The next year, I proved to myself that I could.

That alone would have been enough for a lot of people.

But something changed after that.

I started racing more. I became more competitive. I stopped looking at events only as something to complete and started asking how well I could perform.

That led to a conversation with some friends during the fall.

I told them I was going to race the Cream Puff the following year on a singlespeed and try to win the singlespeed class.

They laughed.

Their Doubt Exposed My Own

It would be easy to tell this as a story about proving other people wrong.

That isn’t really what happened.

Their opinion wasn’t the most important part.

What mattered was that their reaction made me realize I didn’t know whether I could do it either.

Their laughter exposed my own self-doubt.

Could I really race 100 miles on a mountain bike with one gear? Could I compete for the singlespeed win? Could someone who had needed around 14 hours just to finish become competitive near the front of the race?

I didn’t know.

That was the real issue.

It wasn’t that they didn’t believe I could do it. It was that their reaction made me realize I wasn’t sure I believed it either.

That doubt could have stopped me.

Instead, I decided to find out.

I Didn’t Need More Confidence. I Needed a Plan.

I researched what it would take. I built a training plan. I focused on that goal for the next seven months.

I didn’t simply ride more and hope things worked out. I trained for the specific race I wanted to have.

I worked on endurance, climbing, strength, pacing, equipment, nutrition, recovery, and preparation.

Every part of the plan was built around answering one question:

Could I become the person capable of doing what I had said I was going to do?

The answer wasn’t going to come from talking about it. It wasn’t going to come from positive thinking. It wasn’t going to come from arguing with the people who laughed. It was going to come from the work.

That year, I finished fifth overall in around 10 hours.

And I won the singlespeed class.

The next year, I finished third overall and won singlespeed again in around nine hours and 30 minutes.

The year after that, I finished second overall, won the singlespeed class again, and finished about 15 minutes behind the overall winner in roughly nine hours and 15 minutes.

Think about that progression.

My first attempt ended after more than 15 hours without a finish. The next year, I finished in around 14 hours. A few years later, I was second overall in approximately nine hours and 15 minutes while racing a singlespeed.

The biggest change wasn’t the time.

It was the question I was asking myself.

At first, the question was: Can I do it?

Eventually, the question became: What can I do next?

Competition Changes You

Competition does more than measure performance.

It changes the person competing.

It forces you to face failure and defeat, not as ideas, but as real experiences.

You prepare. You make sacrifices. You put in the work. You give everything you have.

And sometimes you still lose. Sometimes you don’t finish. Sometimes someone else is simply better. Sometimes your plan doesn’t work.

Then you have to decide what happens next.

You can make excuses. You can blame the course, the conditions, the competition, the equipment, or the people around you. You can quit. You can lower the goal.

Or you can learn from the result, adjust, and come back better prepared.

That process develops something you don’t get from simply participating.

It teaches you how to lose without allowing the loss to define you. It teaches you how to separate disappointment from defeat. It teaches you that failure may describe what happened, but it doesn’t have to determine what happens next.

That isn’t a lesson you learn once.

Competition makes you face it over and over again.

You Learn How Deep You Can Go

Most people don’t really know where their limits are.

They may have an idea. They may believe they know.

But until you push far enough to reach the place where your mind is looking for a way out, you don’t really know.

Competition takes you there.

In a sprint, everything is compressed into a few seconds. There’s no time to recover from a mistake. You have to commit fully, even when every part of you is under stress.

In an endurance event, the pressure is different.

You have to manage fatigue, pain, nutrition, pacing, equipment, doubt, and the passing of time. You have to keep making good decisions when you’re tired. You have to keep moving after the excitement is gone. You have to deal with the fact that the finish still feels far away.

In a multi-day race, you may have to wake up the next morning and do it again.

That’s where endurance becomes more than physical.

It becomes mental.

Endurance isn’t simply the ability to tolerate pain. It’s the ability to remain focused when things become uncomfortable. It’s the ability to continue making good decisions while tired. It’s staying committed when the easy motivation is gone. It’s understanding that discomfort doesn’t always mean you’re finished.

You learn that you’re often capable of more than you thought.

But you only learn that by going far enough to find out.

Self-Doubt Isn’t Always the Enemy

People often talk about self-doubt as though it’s something you need to eliminate.

I don’t think that’s realistic.

Sometimes self-doubt is useful.

It tells you that the goal matters. It tells you that you’re attempting something beyond what you have already proven you can do. It shows you the gap between where you’re and where you want to be.

The problem isn’t having doubt.

The problem is allowing doubt to make the decision for you.

When my friends laughed at the idea of me winning the singlespeed class, I could have decided they were right. I could have changed the goal. I could have made an excuse. I could have avoided the risk of failing publicly.

Instead, I used the doubt as a reason to prepare.

That’s an important distinction.

I didn’t overcome self-doubt by convincing myself I was already capable. I overcame it by doing the work required to become capable.

That carries directly into business.

You may not know whether you can build the company, reach the revenue goal, lead the team, win the account, enter a new market, or compete with a larger organization.

That uncertainty is normal.

The answer is rarely to wait until you feel completely confident.

Confidence often comes after preparation, not before it.

There’s a Difference Between Wanting a Result and Training for It

A lot of people want to win.

Far fewer build their lives around the work required to make winning possible.

Saying I wanted to win the singlespeed class was easy. Training for seven months was the hard part.

The race was one day. The result was created during all the ordinary days leading up to it.

That’s where sports and business are closely connected.

A business owner may want more revenue, better employees, stronger client retention, a better reputation, or a more valuable company.

But wanting the result doesn’t create it.

You need a plan. You have to understand what’s currently holding you back. You have to measure progress. You have to work consistently, including when no one is watching and when the result still feels far away.

A goal without a plan is mostly a preference.

The Cream Puff taught me that the size of the goal matters less than whether I’m willing to organize my actions around achieving it.

Effort Matters, but It Isn’t Enough

My first Cream Puff attempt took more than 15 hours.

No one could honestly say I didn’t put in effort.

But the effort wasn’t enough to finish.

That’s a hard lesson in sports and in business.

We naturally want effort to guarantee the result.

It doesn’t.

You can work hard and still use the wrong strategy. You can train a lot and still prepare poorly. You can spend a lot of time on something that isn’t moving you forward. You can give everything you have and still find out someone else was stronger, smarter, or better prepared.

Effort matters. But effort has to be directed.

After my first attempt, the answer wasn’t simply to try harder in the same way.

I needed to become better prepared.

That required learning, changing, and being honest about what the race demanded.

Business owners and leaders face the same thing.

Working long hours doesn’t automatically mean you’re working on the right things. Being tired doesn’t prove you were effective. Being busy doesn’t mean you’re making progress. Good intentions don’t guarantee good results.

The important question isn’t only whether you worked hard.

It’s whether the work was producing improvement.

Eventually, you have to look at the result.

Did revenue grow? Did profit improve? Did clients receive better service? Did the team get stronger? Did we become more efficient? Did the work solve the problem?

The scoreboard doesn’t tell the entire story, but it tells part of it.

The purpose of the scoreboard isn’t to make you feel bad.

It’s to keep you honest.

Experience Doesn’t Automatically Mean Improvement

Competing more doesn’t automatically make someone better.

A person can race for years and continue making the same mistakes.

The same is true in business.

Someone may have 20 years of experience, or they may have repeated the same year 20 times.

Time alone doesn’t create improvement.

Improvement requires intention. It requires reviewing performance. It requires accepting feedback. It requires working on weaknesses. It requires changing your approach when the current approach isn’t working.

Athletes who improve don’t only practice what they already do well. They work on what’s costing them performance.

Business leaders need to do the same thing.

That may mean addressing poor follow-up. It may mean improving communication. It may mean admitting a sales process isn’t working. It may mean dealing with a team issue that has been avoided. It may mean building better systems. It may mean changing a strategy that worked five years ago but no longer works today.

Most people already know where they’re weak.

The hard part is being willing to work on it.

Different Races Require Different Strategies

Road racing, cyclocross, mountain biking, and endurance racing all involve a bicycle.

That doesn’t make them the same.

Each one demands something different.

Road racing requires positioning, patience, timing, teamwork, and knowing when to make a move. Cyclocross requires repeated effort, quick recovery, technical skill, and the ability to adapt when things get messy. Mountain biking requires judgment, handling, endurance, and the ability to stay composed when the terrain becomes unpredictable. Endurance racing requires pacing, preparation, patience, mental toughness, and the discipline to continue after the initial excitement is gone.

Business works the same way.

A strategy that works in one market may fail in another. What works when a company is small may stop working as it grows. The skills required to start a business aren’t always the same skills required to lead a team.

Some situations require speed. Some require patience. Sometimes you attack. Sometimes you wait. Sometimes you work with the group. Sometimes you make the move alone.

The key is understanding the race you’re actually in.

Too many people use the strategy they’re most comfortable with instead of the strategy the situation requires.

Endurance Teaches You to Think Beyond Today

Endurance racing may be the closest comparison to building a business.

You can’t get through an endurance event on excitement alone.

You have to prepare for the parts no one sees. You have to manage your pace, nutrition, equipment, recovery, and mental state. Small mistakes early can become big problems later.

Business works the same way.

Weak systems may not hurt immediately. Poor hiring decisions can take time to show up. Bad communication can build frustration slowly. Ignoring cash flow, client service, culture, or follow-up may not create a crisis today.

Over time, those decisions compound.

Endurance teaches you to think beyond the immediate moment.

It also teaches you that motivation is unreliable.

At some point, motivation fades. You get tired. Conditions get worse. The finish still feels far away.

That’s when discipline takes over.

Business owners know that feeling.

Starting something can be exciting. Building it day after day is different.

The real test comes after the excitement is gone and the work still needs to be done.

Managing Teams Taught Me That Talent Isn’t Enough

Managing cycling teams gave me a different view of performance.

A team can have talented individuals and still perform poorly.

Talent alone isn’t enough.

People need clear roles. They need trust. They need communication. They need accountability. They need to understand the goal.

In cycling, not every rider can chase every move. Not every person can be the protected rider. Sometimes your job is to create an opportunity for someone else. Sometimes the strongest thing you can do is sacrifice your own result for the team.

Business teams work the same way.

Hiring talented people isn’t enough.

Leaders have to create an environment where people can perform.

That means setting expectations. It means giving people the tools and support they need. It means having difficult conversations. It means addressing problems early. It means making sure each person understands how their role connects to the larger goal.

A leader can’t demand better results while ignoring the conditions required to produce them.

Promoting Races Taught Me to See the Whole Course

As a racer, you see the course in front of you.

As a promoter, you see everything required to make the race possible.

You think about the route, permits, safety, timing, volunteers, communication, logistics, risk, and all the details most participants never see.

That perspective carries directly into business.

Clients and employees often see the visible result.

They see the meeting, the product, the service, the proposal, or the transaction.

Leaders have to see the entire system behind it.

A successful outcome may depend on dozens of things working correctly before the client sees the final result.

That’s one of the biggest differences between individual performance and leadership.

As an individual, your responsibility is to perform your role well.

As a leader, your responsibility is to make sure the course is ready, the team is prepared, and the entire operation can support the result.

You’re no longer only responsible for how well you ride.

You’re responsible for creating the environment where others can perform too.

The Goal Is to Change the Question

The Cream Puff taught me that a difficult goal can change more than a result.

It can change how you see yourself.

I went from being someone who didn’t finish after more than 15 hours to someone who finished second overall and won the singlespeed class three years in a row.

That didn’t happen because I suddenly decided to believe in myself.

It happened because I set a goal, built a plan, did the work, measured the results, and kept improving.

Eventually, the self-doubt became less powerful because I had evidence.

I had proven to myself that my current limits weren’t necessarily permanent.

That’s the real value of competition.

It isn’t only about beating someone else.

It’s about learning how to face failure and come back. It’s about finding out how deep you can go. It’s about discovering what happens when you stop accepting your first result as the final answer.

Showing up matters. Participating matters. Finishing matters.

But there may come a point when simply completing the race is no longer enough.

You begin asking what you can improve. Then you begin asking what you can compete for.

Eventually, if you keep doing the work, the question changes completely.

It’s no longer: Can I do it?

It becomes: What can I do next?

RS
Richard Sweet, Founder & Principal Advisor

Richard Sweet runs Vantage Point Risk, an independent insurance and risk advisory for business owners, real estate investors, commercial property owners, and families. The Vantage Point is where he shares the operating principles behind how the agency is built and how he helps clients think about risk and growth.

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