Avoiding "Reckless Retirement" Part #3

Designing Your Perfect Retirement

So, you’ve figured out that you’re ready to retire, and you’ve taken a hard look at how life will change when work is no longer the centerpiece of your identity. Now comes the fun (and sometimes overwhelming) part: designing what’s next. Because here’s the truth—retirement isn’t just about not working; it’s about creating a life you actually want to live. The next critical question you need to ask yourself is:

"What do I want my retirement to look like? What do I want to DO with my time?"

For years, your schedule has been dictated by meetings, deadlines, and responsibilities. Now, your time is yours. And while that might sound exciting, it can also be surprisingly paralyzing. Without a clear vision, time has a way of slipping by, and before you know it, you’re waking up thinking: What am I supposed to do today?

That’s why this next step is so important. Instead of just drifting into retirement, let’s take a proactive approach and intentionally design your ideal day, week, and month—one that balances purpose, relaxation, adventure, and connection.

What does your perfect retirement look like?

This exercise will help you map out your ideal retirement lifestyle, so you wake up every day excited about what’s ahead.

Step 1: Look Back Before You Look Forward

Before designing your future, take some time to reflect on the past. Patterns in your past can reveal what truly brings you joy.

Ask yourself:

1. What were the happiest, most fulfilling periods of my life?

   • What was I doing?

   • Who was I spending time with?

   • What made those moments so meaningful?

2. What hobbies, interests, or activities have I enjoyed throughout my life?

   • Are there things I used to love that I stopped doing due to work or other commitments?

   • Have I always wanted to try something but never had the time?

3. What moments made me feel the most “alive” and energized?

   • When was the last time I lost track of time because I was so engaged?

   • What experiences gave me a deep sense of accomplishment or joy?

4. What do I regret not doing more of in my working years?

   • Travel?

   • More time with family?

   • Hobbies or creative pursuits?

Step 2: Design Your Perfect Day

Imagine you wake up in retirement excited about the day ahead. What does it look like?

Ask Yourself:

• Morning: How do I want to start my day?

  • Do I savor a slow morning with coffee and a book?

  • Do I exercise first thing?

  • Do I enjoy volunteering or mentoring early in the day?

    
    

• Midday: How do I stay engaged and energized?

  • Am I learning something new?

  • Do I schedule social activities?

  • Am I working on a personal project?

    
    

• Afternoon: How do I want to spend my time?

  • Do I want time for relaxation or creativity?

  • Do I enjoy being outside or working on a passion project?

    
    

• Evening: How do I want to wind down my day?

  • What social activities do I want to include?

  • Do I prefer quiet nights at home, dinners with friends, or cultural events?

    
    

Exercise: Write Your Ideal Day Schedule

While no two days have to be the same if you don't want them to be, building a broad, flexible outline can provide you with structure to keep you focused.

List your activities and the amount of time you will spend on each one. Use your reflections from step to help you build your day.

Here is an example:

7:00am Coffee & Today Show

8:00am Exercise (Gym/Walk/Yoga)

10:00am Shower, get ready for the day

11:00am Work/Errands - Must Do's

Noon Lunch with X

2:00pm Work/Class/Errands/Calls with family/friends

5:00pm Prep dinner

6:00pm Dinner

7:00pm TV/Reading

10:00pm Bed Time

Step 3: Design Your Perfect Week

A fulfilling retirement is about balance—between rest and activity, solitude and social connection, routine and spontaneity.

Ask Yourself:

• How much structure do I want?

  • Do I want set routines (e.g., gym every Monday, lunch with friends every Wednesday)?

  • Or do I prefer flexibility?

• How much social interaction do I need?

  • Do I enjoy daily social plans or just a few meaningful meetups per week?

• What activities do I want to include every week?

  • Exercise?

  • Learning (classes, reading, or creative pursuits)?

  • Volunteering or mentoring?

  • Family time?

    
    

Exercise: Using your idea of a perfect day, step back and consider things you may want to include weekly to sketch out your ideal weekly schedule

• Monday: ________________________

• Tuesday: ________________________

• Wednesday: ________________________

• Thursday: ________________________

• Friday: ________________________

• Saturday: ________________________

• Sunday: ________________________

Step 4: Design Your Perfect Month

Not every activity fits neatly into a weekly routine. Some things are better planned on a monthly basis, like travel, larger projects, or special events.

Ask Yourself:

• What do I want to look forward to each month?

  • A weekend getaway?

  • A family gathering?

  • A new project or class?

• Are there experiences or adventures I want to schedule regularly?

  • Road trips?

  • New restaurants or cultural events?

• Do I want to set monthly goals?

  • Reading a certain number of books?

  • Completing a creative project?

    
    

Exercise: Write Down One or Two Meaningful Events for Each Month

• January: ________________________

• February: ________________________

• March: ________________________

• April: ________________________

• May: ________________________

• June: ________________________

• July: ________________________

• August: ________________________

• September: ________________________

• October: ________________________

• November: ________________________

• December: ________________________

Step 5: Design Your Ideal Year

When you step back and look at the big picture, your retirement years can be shaped with intention and excitement.

Ask Yourself:

• What major events or milestones do I want to plan for each year?

  • Big trips?

  • A creative or professional goal?

  • Family gatherings?

• How do I want to grow each year?

  • Do I want to master a new skill?

  • Take on a leadership or mentoring role?

  • Prioritize a health or wellness goal?

• What traditions or seasonal activities do I want to establish?

  • Summer travel?

  • Holiday family gatherings?

    
    

Exercise: Write One Big Goal or Experience for Each Year in Retirement

• Year 1: ________________________

• Year 2: ________________________

• Year 3: ________________________

• Year 4: ________________________

• Year 5: ________________________

This exercise helps ensure that your retirement years don’t just “happen” to you—but that you design them with purpose and excitement. Keep your plans flexible so that you can incorporate new things along the way.

Final Step: Take Action!

After completing this exercise, ask yourself:

✅ What’s one step I can take right now to start creating my ideal retirement?

✅ What changes do I need to make in my current routine to align with my vision?

You’ve designed your ideal retirement day, week, month, and year—now it’s time to turn vision into action.

Retirement isn’t something you just fall into—at least, not if you want it to go well. The most successful retirees treat their transition like a major project—because it is.

So, what should you be doing in the 12 months leading up to retirement to set yourself up for success?

In my next post, I’ll walk you through a structured, step-by-step retirement lifestyle plan, breaking down exactly what to focus on each month before you retire—from financial and logistical prep to testing out your new routines before the big day arrives.

Think of it as your Retirement Launch Plan—so when your first official day of retirement arrives, you’re not asking, “Now what?” but instead thinking, “Let’s go!”

What will you create?