Avoiding Reckless Retirement Part #4

Building your Launch Plan

In the previous three posts we examined the crucial questions you need to ask yourself when you are beginning to think about retirement. Now that you have some answers, it is time to build our your launch plan

Taking a project management approach with timetables and milestones will help keep you on track along the way.

Step 1: Define the Retirement "Project Scope" (6–12 Months Before Retirement)

📌 Key Question: What does a successful retirement look like for me?

💡 Just like launching a new business line, retirement requires a clear vision, risk assessment, and success measures.

Milestones:

✅ Clarify your vision. Do you want to consult, volunteer, travel, pursue hobbies, or start something new? Write a retirement mission statement like you would for a business.

✅ Assess gaps. Identify areas where you feel least prepared (purpose, social life, structure, health, finances, etc.).

✅ Set success metrics. What will make you feel like you’ve “achieved” a fulfilling retirement? (E.g., meaningful activities, strong relationships, financial confidence, etc.)

Step 2: Build a Transition Roadmap (6 Months Before Retirement)

📌 Key Question: What are the steps I need to take to ensure a smooth transition?

💡 Think of this like succession planning and change management—handing over leadership while preparing for your next chapter.

Milestones:

✅ Create a detailed transition plan for your role. Identify key responsibilities, train your successor, and document critical knowledge.

✅ Develop a phased approach. Consider whether a gradual step-down (part-time work, consulting, board work) makes sense.

✅ Build your post-retirement calendar. Start outlining what your weekly routine will look like.

✅ Have key conversations. Talk with your spouse/partner, family, and close friends about expectations and boundaries.

✅ Test your assumptions. Take extended time off (e.g., a month-long sabbatical) to experience what a typical retirement day might feel like.

Step 3: Execute the Transition Plan (3 Months Before Retirement)

📌 Key Question: How do I ensure a seamless exit while preparing for my next phase?

💡 This is similar to handing off a major project or stepping away from a leadership role while ensuring a smooth transition.

Milestones:

✅ Announce your retirement plan. Communicate your timeline to key stakeholders.

✅ Begin disengaging from work identity. Reduce workload, transition leadership, and start immersing yourself in post-career activities.

✅ Test-drive new routines. Experiment with potential retirement activities (e.g., volunteering, hobbies, advisory work) before you fully retire.

✅ Start connecting with new networks. Join groups, attend events, and build your post-work social circle.

✅ Do a “retirement dry run.” Spend a few weeks living as if you’re already retired—how does it feel? What needs tweaking?

Step 4: Optimize and Adjust (0–6 Months Post-Retirement)

📌 Key Question: Am I thriving in retirement, or do I need to tweak my approach?

💡 This is the post-launch optimization phase—assessing performance and adjusting the strategy accordingly.

Milestones:

✅ Conduct a 90-day review. Just like in a new job, assess how retirement is going. Are you staying engaged? Do you feel purpose-driven?

✅ Identify gaps. Are you missing social interaction, intellectual stimulation, or structure? Make adjustments.

✅ Fine-tune your schedule. Balance productivity and relaxation—too much of either can lead to frustration.

✅ Seek new opportunities. Whether it's mentoring, a passion project, or something unexpected, stay open to evolving interests.

Step 5: Long-Term Legacy Planning (Ongoing)

📌 Key Question: What impact do I want to leave beyond my career?

💡 This is legacy-building—similar to shaping an organization's long-term impact.

Milestones:

✅ Define your long-term goals. Do you want to build a legacy, mentor, invest in philanthropy, or create something lasting?

✅ Create an impact plan. What are the specific actions you’ll take to make a difference? (Writing, speaking, teaching, nonprofit work, etc.)

✅ Continue evolving. Just as businesses pivot, allow yourself to adjust and redefine retirement goals over time.

By treating retirement like a well-managed project, you gain clarity, direction, and confidence in your next phase. A successful retirement isn’t about stepping away—it’s about stepping into something new with purpose and excitement. Planning helps increase your chances of success.