I heard the “snap” in my foot during a training run and I knew it wasn’t just a warning sign – it was a moment that forced a tough choice. Do I keep pushing through the pain in hopes that things will get better, or do I pull back, play it safe, and “live to run another day”?

For property management entrepreneurs, this decision is all too familiar. Every day, we’re faced with the choice between pushing for short-term wins or investing in long-term success. 

As I prepare for the Moab 240 (held on October 11th-16th, 2024), a 240-mile ultramarathon, I find myself wrestling with a decision that mirrors the tough calls we have to make in business: Should I show up and do my best no matter the circumstances, or should I play it safe and think about the long-term?

The Game Plan – Knowing the Mission and Vision

We all need a game plan, whether we’re on the trail or in the office. For months, my game plan was crystal clear: I was training hard to compete in the Moab 240. That race was my mission, it is my “A Race” for the year. But during a 20-mile training run up a steep incline, everything changed. As I stepped onto a rocky ledge, I felt a snap in the arch of my foot. By the time I hobbled back to my truck, it was clear that I had a serious injury.

An MRI confirmed it: an 80% tear in my plantar fascia. My game plan suddenly shifted from focusing on completing the race to asking myself a bigger question—what is my long-term vision? What do I want more: to complete this race, or to be able to run for many more years?

In business, the same question often arises. We create a mission and vision for our company, but sometimes life throws us a curveball. How we respond to these challenges determines whether we’re playing the short game or the long game. I often say “it’s not what happens but rather what happens when something happens.” Meaning things happen and it’s more important to focus on what we do about it when we are met with unexpected challenges.

The Scoreboard – Measuring Short-Term vs. Long-Term Success

In our property management businesses we track our success through KPIs and OKRs. We monitor our lead generation, vacancy rates, and client satisfaction to make sure our businesses are healthy in the short term. But we also set OKRs—objectives that look beyond today’s metrics toward tomorrow’s growth. This balance between short-term KPIs and long-term OKRs is crucial.

When I received the diagnosis of an 80% tear, I had to start weighing my own KPIs and OKRs. Could I still run Moab 240, knowing the damage to my foot? Could I finish the race, or would pushing through lead to a more severe injury that could prevent me from running again in the future? My short-term KPI was clear: How much pain can I endure, and will my body hold up? But my long-term OKR was just as important: Will I be able to run at all in the future if I ignore this injury?

Entrepreneurs face the same kind of choices. Do we push through for a short-term win, knowing it might lead to bigger problems down the road? Or do we pull back, give our businesses time to heal, and position ourselves for long-term success?

Balancing Risk and Reward – Lessons from Ultrarunning and Entrepreneurship

Success in business and ultrarunning both require a high tolerance for risk. AsEntrepreneurs we take risks all the time—whether it’s expanding into new markets, hiring more staff, or investing in new technology. But when is the risk worth it? And when does it make sense to hold back?

In running, the risks are often physical. Push too hard, and you could face long-term injury. In business, the risks are financial, operational, or even emotional. Should you push forward with a new project or initiative, knowing it could stretch your resources? Or should you take a step back, regroup, and plan for a more sustainable future?

Both in business and on the trail, the key is knowing when to push and when to pause. The ability to evaluate risk and reward is what separates successful entrepreneurs—and successful ultrarunners—from the rest.

The Importance of Listening to the Signs

As I walked back to my truck after feeling that snap in my foot, I couldn’t ignore the signs. My body was telling me something was wrong. The injury didn’t happen out of nowhere—there had been smaller signs along the way, which I had ignored.

In business, the signs might be financial stress, declining client satisfaction, or staff burnout. Ignoring these signals can lead to bigger problems. Just as I had to recognize that pushing through my injury could cause more damage, entrepreneurs must recognize when their business is sending warning signs. It’s not about quitting; it’s about making strategic decisions that protect the long-term health of the business.

The decision of whether to run Moab 240 is still hanging in the balance for me. But one thing is clear: In both running and business, the game plan and scoreboard are what help guide our decisions. Having a clear vision for the future and knowing how to measure success—whether through KPIs, OKRs, or a personal health check—are the tools that allow us to make informed, strategic choices.

For now, I’m weighing the risks, and I’ll share my decision in the next update. In the meantime, keep your eyes on your own game plan and scoreboard, whether you’re running an ultramarathon or growing your property management business.