Three Ways to Turn a Setback into Progress

Fall is my favorite time of year here in Virginia—the cooler temperatures, colorful leaves, and, of course, football season.

Some of my fondest memories are from playing football for Coach Dick Sheridan at Furman University in the 1980s. We celebrated “David vs. Goliath” victories over much larger schools, including South Carolina, Georgia Tech, and N.C. State.

When you’ve worked hard alongside your teammates, those wins stay with you. But so do the losses.

In business and in life, we don’t always get the outcome we want. A promising opportunity falls through. A prospect chooses someone else. A goal we’ve worked toward slips out of reach.

Winning feels better. But a loss can still become the starting point for something valuable—depending on what we do next.

I learned that firsthand when my coaching firm made it to the final two for a team coaching engagement—and wasn’t selected.

After getting so close, I felt a wave of disappointment and second-guessing. What had I missed? What could I have done differently?

Then I had to practice what I preach: put the setback in perspective, learn from it, and prepare to compete again.

That experience reminded me why I believe the next best thing to winning can be losing—if we use it well.

1. Put the loss in context.

One disappointing outcome doesn’t erase everything that went into it.

My firm had been selected as one of five recommended coaching firms from a much larger field. We went through interviews, reference checks, and a proposal process before reaching the final two.

We didn’t win the engagement. But making it that far told me something, too. Our experience and approach had earned serious consideration.

That didn’t eliminate the disappointment. It gave me a more complete picture.

After a setback, it’s easy to turn “I didn’t win this opportunity” into “I’m not good enough.” Those are very different conclusions.

Before judging yourself—or your team—ask:

What went well? Where did we make progress? What does this outcome actually tell us, and what are we assuming?

You can acknowledge a loss without letting it define you.

2. Look for information you can use.

Losing business after a lengthy selection process can be exhausting.

You invest time in conversations, follow-up meetings, references, and a tailored proposal. Then comes the waiting. When the answer is no, your first instinct may be to put the whole experience behind you.

But there may be something worth learning before you move on.

In this case, the team was willing to explain why they chose another firm. Hearing that feedback wasn’t comfortable, but it helped me identify ways to improve how I packaged and presented my services.

Not every prospect will offer feedback. And not every decision means you did something wrong. Sometimes another provider is simply a better fit.

Still, it’s worth asking:

“What most influenced your decision?”

“Was there anything about our approach that wasn’t clear?”

“What could we have done better during the process?”

Listen before defending your position. Look for patterns across experiences rather than rebuilding your entire approach around one person’s opinion.

A loss can give you information a win might not. The value comes from deciding what to do with it.

3. Make an adjustment—and get back on the field.

A football team can’t spend the rest of its season reliving one bad game.

The coaches review the film, identify what needs to change, and get the team ready for the next opponent.

We need a similar approach in business and in life.

Give yourself room to feel disappointed. Then turn the review into a decision.

Do you need to ask better questions? Explain your value more clearly? Prepare differently? Strengthen a skill? Pursue opportunities that are a better fit?

Choose a specific adjustment you can put into practice.

After losing that coaching engagement, I identified what I wanted to emphasize in my next presentation. I also began reaching out to new prospects to replenish my pipeline.

That second step mattered. Learning from the loss helped me improve. Taking action helped me regain momentum.

Reflection is useful when it changes what we do next. It becomes less useful when we keep replaying the same disappointment without making a decision.

The rest of your season is still ahead.

You don’t have to pretend losing feels good. And you don’t have to squeeze a grand lesson out of every disappointment.

But you can ask three practical questions:

What should I keep in perspective?

What can I learn?

What will I do next?

That’s how a setback becomes part of your progress rather than the end of it.

Get back on the field. There’s another game to prepare for.

Bob David — Speaker, Coach, and Consultant

For more information about Bob’s coaching services, visit BobDavidLive.com/coaching-for-financial-advisors/ or contact Bob to discuss your goals.

Originally published September 2016; updated October 2026.