How often do you tell yourself where you should be by now?

“I should have this figured out.”

“I should know what comes next.”

“I should be further along.”

“Should” is an argument with reality.

Few thoughts are more discouraging.

Sometimes these thoughts show up when life feels uncertain or overwhelming.

But just as often, they surface when you’re doing well and know your next chapter deserves more than a default decision.

Many high-performing leaders leave uniformed service with tremendous experience, proven leadership skills, and a strong desire to keep contributing in meaningful ways. They are not in crisis. They simply want clarity about what comes next.

Others are navigating real uncertainty and trying to regain their footing.

Wherever you find yourself, “should” can keep you stuck in expectations, assumptions, and plans that no longer fit.

The truth is, none of us can rewrite the past. What we can do is take ownership of the present and make intentional choices about the future.

Maybe you’re at a crossroads — not because you’ve failed, but because you want to be more deliberate about how you invest your time, talents, and energy in this next season of life.

So … now what?

Get real.

Be honest about where you are today and what matters most. Have the courage to take the next step, even if it looks different from what you once imagined.

Instead of beating yourself up with “shoulda, coulda, woulda,” choose honesty, integrity, and courage.

Be honest about where you are today.

Clarify what matters most.

Stop living according to someone else’s script.

Take the next right step.

You can build a life and career that reflect who you are and what matters most.

That doesn’t mean life will be free of stress, setbacks, grief, or uncertainty. It means you’ll have a clearer sense of who you are and where you want to make your greatest contribution.

Despite the workshop’s name, Dare to Dream: Live the Life You Love! is not about wishful thinking. It is a practical, structured process that helps you clarify what matters most and align your next chapter accordingly.

Whether you are preparing to leave active duty, evaluating your second career, or simply sensing that you are ready for a more intentional next chapter, clarity is a competitive advantage.

Participants have used Dare to Dream to make bold, thoughtful decisions about what comes next.

“My wife and I decided to take exactly one year as a gap, and it was the best decision I ever made,” one attendee said. “The time allowed me to refresh, spend time with my family, and reflect on the next portion of the journey. I would never have believed at the beginning of the course that I would be working in Washington, D.C., for NGAUS.”

“Dare to Dream was a significant contributor to where I am right now in my journey,” said another. “Since our last discussion, I have finished my book, launched an online course, begun teaching at Tulane University, and will soon represent myself at my first private-sector conference.”

So … why not you?

Forget “should.” Stop measuring your life against a script that no longer fits.

Get real about who you are, what matters most, and where you can make your greatest contribution.

Your next chapter deserves the same intentionality and leadership that defined your service.