Retirement Reset: Letting Go to Move Forward

By Dave Smith, The Ultimate Retirement Coach

Retirement offers more than rest—it offers reinvention. But reinvention isn’t always about adding new goals. Often, the most meaningful progress comes from letting go. The titles, habits, and silent expectations that shaped our past don’t always serve our future.

So ask yourself: What must I release in order to create the lifestyle I truly want?


💡 One Idea: Chase Lifestyle, Not Labels

For decades, many of us chased promotions, titles, and recognition. And sure, they can be satisfying—for a time. But in retirement, status can become a trap. When you let go of the need for labels and titles, you free yourself to pursue what really matters: a life that feels good on the inside, not just one that looks good on the outside.

“Chase your desired lifestyle, not your desired title. People are blinded by status and labels. Once you release the need for a specific title, there is almost always an easier path to living your preferred lifestyle.”
Dave Smith

🧠 Insight from Walt Kelly:

“Having lost sight of our objectives, we redoubled our efforts.”
Walt Kelly, Pogo

Sometimes we’re pushing hard in the wrong direction. Retirement is your chance to realign your energy with your objectives, not your old identity.


❓ One Powerful Question:

What do you need to give up to make space for what you would like to achieve?

New chapters require new space. Whether it’s time-consuming habits, old responsibilities, or even certain relationships—every meaningful gain requires a conscious letting go.


🛠️ One Practical Exercise: “The Let-Go List”

This exercise is about clearing the clutter—mental, emotional, and calendar-based—so your next phase of life has room to grow.


Worksheet: The Let-Go List

CategoryWhat’s Holding You Back?What You’ll Gain by Letting GoFirst Small Step to Release It
🧠 Mindsete.g., Needing to feel important through titlesMore freedom to choose your pathAcknowledge it in writing
📅 Time Commitmentse.g., Volunteering out of obligationEnergy to invest in passionsPolitely step down or set limits
🤝 Relationshipse.g., People who drain your energyEmotional peace, better boundariesReduce contact, clarify boundaries
🎯 Expectationse.g., Thinking retirement must look a certain wayPermission to do it your wayChallenge one outdated assumption
💬 Unspoken Assumptionse.g., Assuming your spouse wants the same thingsOpen communication, less resentmentSchedule a conversation this week

💭 Reflection Prompt:

  • Which release feels the scariest?

  • Which one feels the most freeing?

  • What support or accountability do you need?


🗣️ From Dave: Next Play Mentality

Let’s be real—sometimes we get it wrong. We hold on too long. We make a bad call. That’s okay. As I often say:

Take great care to avoid mistakes when the decision is hard to reverse. But if you make one—don’t beat yourself up. Just make the best next choice. That’s Next Play Mentality.

Your retirement isn’t ruined by one mistake. It’s defined by your next decision.


📚 Bonus Wisdom from Schopenhauer:

“The art of not reading is a very important one… A precondition for reading good books is not reading bad ones: for life is short.”
Arthur Schopenhauer, Essays and Aphorisms

This doesn’t just apply to books—it applies to your attention, time, and energy. Be selective. Life is short. Retirement is shorter.


🎯 Final Thoughts:

Retirement success isn’t built on more—it’s built on less but better. Let go of what no longer serves you, so you can step fully into the life that does.

Stay intentional. Stay curious. And remember:
Letting go isn’t loss—it’s space for something better.