#010 - Learning to lose gracefully

Learn this system for processing losses to grow in more ways than one.

Like a one-two punch to the gut, both emails arrived on the same day.

I had been waiting weeks to hear back on two big new client proposals.

Either would have been a tentpole client for 2024.

We had lost them both.

Reflecting on the losses two weeks later, I’m proud of what I did next.

I put my phone away and continued my day, at peace with the outcome.

After years of avoiding situations where failure might be an option, I have learned to embrace losing.

More than that, I have developed a system for processing failures.

It allows me to lose gracefully, mine losses for learning, and embrace losing to fuel growth.

Here it is:

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1. Learn to lose.

Learning to lose means having a repeatable system to process failure in a way that ensures losing doesn’t break your winning spirit.

Contain mourning

Humility is one of failure’s greatest gifts.

Feeling disappointed, frustrated, and even a momentary pang of despair in the face of failure is only human.

But it’s important to avoid getting trapped in a trough of self-pity.

Allocate a specific period of time to mourn your loss.

The specific amount of time is less critical.

What counts is committing that when that time has expired, you will get back on the horse with renewed optimism and drive to win.

In the case of my recent losses, I gave myself the rest of the day to “feel the feels”: disbelief, disappointment, defeat, frustration.

Then I let it go and asked myself: “Okay, what’s next?”

Separate story from reality

It’s easy to make up stories about what happened in the room where the decision was made.

But these stories are mentally draining and rarely true.

Step back, challenge your stories, and separate fact from fiction.

Shields down. Grace up.

How you respond to a loss demonstrates your character and values.

When we lose, we often use shields to neutralize the loss and protect our sense of self.

• We blame others: “They just didn’t get my proposal.”
• We suspect others: “I was brought in as column fodder, they wanted person X from the start.”
• We minimize our disappointment: “I didn’t really want that client anyway.”

Losing gracefully is having empathy and considering how your response might make the client feel.

The person on the other side probably already feels horrible about letting you down. Don't be a jerk.

Show gratitude for the opportunity. Wish them well in their pursuit. Be curious and open to feedback.

Here was my response to one of the firms:

2. Lose to learn.

Embracing loss as a teacher requires us to confront the reality of our results, take accountability for our actions, and evolve.

Seek input

You only walk away empty-handed from a loss if you fail to use it as an opportunity to collect data.

Request a debrief with the client to help you understand how to put your best foot forward in the future.

It can help to reiterate that you accept their decision and are not trying to change their mind, only learn, improve, and grow.

Ask open-ended questions like:

• “What were the deciding factors that led to your decision?”
• “Where could I focus the next time to improve?”
• “What would have had to been true for me to earn your business?”

Then stop talking and listen.

Own it

Go get a glass of water because here comes the tough pill to swallow…

Ultimately, the only person responsible for your failure is you.

The biggest unlock in embracing failure came from asking myself:

"How did I contribute to this outcome?"

I go through a checklist, including:

• Did I properly qualify the opportunity?
• Did I follow my process?
• Did I operate in line with my values and beliefs?
• Did I fully prepare and bring my A-game?
• Am I proud of the work I put forward?

The point of this exercise isn’t to punish yourself but to candidly assess the factors inside your circle of control.

In owning the two recent losses:

✅ I'm proud of the quality of the work and presentations

✅ We upheld our values and put our best foot forward

❌ We could have better qualified the opportunities

Identify Patterns & Evolve

Evolution is often necessary to be successful in your next attempt.

But before overhauling your offer, pricing, positioning, or new business process, look for patterns.

Many freelancers don’t stick with a strategy long enough to learn from or hone it.

Remember, it takes more energy to start something new than it does to upgrade what you already have.

Look for patterns (3+ occurrences) as signals that change is required, not a single data point.

3. Lose to grow.

The ultimate goal isn’t to learn from your losses as a way to stay safe but to fuel growth.

Once you recognize that a winning mindset embraces both success and failure, the fear of losing will be replaced by the confidence to play bigger.

With a system for processing and learning from losses, you’ll see that bigger failures set up bigger growth as a freelance professional.

And that bigger growth will bring bigger wins.

My challenge to you is to play bigger, lose bigger, and ultimately win bigger.

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-Jeff GadwayFounder,

Freelance Marketing Alliance

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