How to Avoid "Reckless Retirement" Part #1

Questions to consider before you jump off the corporate ladder.

If I had planned and executed a project at work as poorly as I did my own retirement, I would have fired myself.

Like many executives, I spent years managing people and projects with detailed plans—goals, milestones, check-ins, the whole nine yards. I agonized over the ripple effects of every decision, crafting meticulous change management strategies to cover every foreseeable outcome. Nothing was left to chance.

Helping people and organizations navigate change was my job. So why didn’t I apply the same rigor to my own transition into retirement? Why did I assume that as long as my finances were in order, I’d just figure out the rest? I guess I thought, How hard could “not working” be? I’d wing it, right?

Wrong. So very wrong.

Since my own reckless retirement in 2022, I’ve made it my mission to help others avoid the painful mistakes that cost me time, money, and—most critically—my sense of self.

What I’ve learned is this: Having enough money to retire gives you the option to retire, but without answering three critical questions, you’re setting yourself up for failure.

In this post (and the next few), I’ll walk you through those three questions—why they matter, how to find your own answers, and how to build a retirement plan that actually sets you up for success.

Because trust me, winging it is not a winning strategy.

Question #1

WHY do I want to retire?

The answer to this question is foundational to everything that comes next. If you get the answer to this one wrong, you could be making decisions that are hard to recover from.

Knowing whether you’re just tired—burned out and ready for something new—or truly ready to step back and shift your life is critical to making the right decision.

Burnout and real retirement readiness can feel eerily similar. But making a permanent decision (retirement) based on a temporary state (burnout) can lead to regret, frustration, and a whole lot of Now what?

Here’s why misdiagnosing burnout as retirement readiness can be a risky mistake:

Burnout is Temporary—Retirement is Permanent (or Hard to Undo)

• Burnout is a condition—caused by chronic stress, exhaustion, and disengagement.

• Retirement is a lifestyle shift—a long-term decision that reshapes your identity, purpose, and daily structure.

• If you retire to escape burnout, you may regret leaving the workforce once you recover.

  
  

✅ Better Approach: Address burnout first — if you can, try a sabbatical, reduced workload, or a job change before making an irreversible decision.

Burnout Can Be Fixed—Retirement Requires a New Purpose

• If burnout is the issue, fixing the underlying causes (workload, stress, lack of fulfillment) can restore your energy and passion.

• If you’re truly ready to retire, you’ll have a clear vision for what’s next—NOT just a desire to escape work.

• Many executives retire out of burnout and realize too late that they weren’t ready for the lack of structure and purpose.

  
  

✅ Better Approach: Ask yourself: If my work conditions improved, would I still want to retire? If the answer is no, you’re burned out—not ready to retire.

Retirement Without a Plan Can Feel Empty

• If you retire just to escape a bad job, but don’t have a clear plan for what’s next, you might experience boredom, isolation, or loss of identity.

• Many executives underestimate how much purpose and intellectual stimulation work provides.

• If you go from 100 mph to zero overnight, you might feel lost rather than relieved.

  
  

✅ Better Approach: Before retiring, build a detailed vision for your post-work life—activities, social circles, new challenges, and goals.

 Burnout Can Lead to Poor Decision-Making

• When you’re exhausted, your decision-making ability suffers.

• You might make a reactionary decision (I need to quit!) instead of a strategic decision (I am ready for my next phase).

• You could walk away from valuable professional relationships, career opportunities, or financial stability because of short-term frustration.

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✅ Better Approach: Give yourself time and space to recover from burnout before making a final retirement decision.

You May Want to Work Differently—Not Stop Working Entirely

• Burnout might mean you need a change, not an exit.

• You might still want to contribute—but on your terms (consulting, mentoring, board work, part-time roles).

• Many retirees return to work in some capacity because they miss the challenge, structure, and connection.

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✅ Better Approach: Experiment with a phased retirement or alternative work structure before making a full break.

So how do you know if you are burned out or ready for retirement?

This self-assessment will help you determine whether you’re experiencing job burnout or if you’re truly ready to retire. Answer each question honestly—if you find yourself leaning heavily toward burnout, it may be time to address work-related stress before making a retirement decision.

Burnout vs. Retirement Readiness Quiz

Section 1: Work Enjoyment & Engagement

1. Do you still find aspects of your job fulfilling?

   A) Yes, I still enjoy some parts of my work.

   B) No, I feel disengaged and unmotivated.

   
   

2. If your workload were reduced or your responsibilities changed, would you still want to retire?

   A) No, I might enjoy working if the stress were reduced.

   B) Yes, I’m ready to step away regardless of changes.

   
   

3. Do you feel intellectually stimulated at work?

   A) Sometimes, stress is overshadowing it.

   B) No, I feel stuck and uninterested.

   
   

Section 2: Energy & Emotional State

4. How do you feel at the start of your workday?

   A) Tired or stressed, but I push through.

   B) Exhausted, dreading the day ahead.

   
   

5. Do you feel emotionally drained or resentful toward your work?

   A) Sometimes, but I believe a break might help.

   B) Yes, I feel completely depleted.

   
   

6. Would taking an extended vacation or sabbatical change how you feel about work?

   A) Probably, I think a break would help.

   B) No, I’d still feel the same about leaving.

Section 3: Future Outlook & Purpose

7. Do you have a clear idea of what you want to do after retiring?

   A) Not really, I just know I don’t want to work like this.

   B) Yes, I have plans and goals I’m excited about.

   
   

8. Are you looking forward to retirement for the opportunities it brings, or just to escape work?

   A) Mostly to escape work.

   B) Because I’m excited for what’s next

   
   

9. Would you consider working in a different capacity (consulting, part-time, board work) instead of fully retiring?

   A) Yes, I still want to contribute in some way.

   B) No, I’m done with the professional world.

   
   

Section 4: Identity & Social Connections

10. Do you have a strong sense of identity outside of work?

    A) Not really, my work is a big part of who I am.

    B) Yes, I have interests and relationships that define me beyond my job.

    
    

11. Do you have an active social life outside of work?

    A) Somewhat, but most of my relationships are work-related.

    B) Yes, I have a strong support network outside of my career.

    
    

Scoring & Results

Mostly A’s → You might be experiencing burnout, not retirement readiness.

Consider taking a break, adjusting your workload, or exploring new career options before making a final decision.

Retirement might not be the right move if work conditions, not work itself, are the problem.

Mostly B’s → You are likely ready for retirement.

If you feel excited for what’s next, have plans outside of work, and aren’t just looking to escape stress, you are likely truly ready to transition.

Key Takeaway:

Before deciding to retire, ask yourself: Am I retiring because I’m ready for a new phase—or because I need relief from my current job?

If it’s the latter, address burnout first—because once you retire, going back is much harder than staying in the game on your own terms.

"Understanding why you want to retire is crucial, but it’s only the beginning. The next big question is: How will things change when work is no longer at the center of my life? Because let’s face it—when your career has dictated your schedule, your priorities, and even your social life, stepping away can feel like a seismic shift. In the next post, we’ll explore what really happens when work no longer defines your days—and how to make sure you don’t end up wondering, ‘Now what?’ Stay tuned!"