Getting There

FINANCIAL GUIDANCE
FOR YOUR LIFE JOURNEY

Designing Your Retirement

Designing Your Retirement

**If you missed part 1 or part 2, they are available on our website at this link.

Last weekend, I had the opportunity to volunteer on behalf of our professional association, The Financial Planning Association, at my local library.

Free financial planning sessions were offered on a first-come, first-served basis. We met for 30-minute sessions to answer whatever questions people had about their personal finances. All volunteers were kept busy. (My husband even came down just to say hello, and he said I was so engrossed by who I was working with, he couldn’t even catch my eye!)

The majority of those I met were discussing retirement, and, as is not unusual in my experience, each had a unique retirement planning need to address.

One wanted to spend more time with their aging mother in another state, and a new grandchild is on the way in this one. They were not yet out of their 50s and would leave some excellent work benefits, including an ever-increasing pension if they stayed. One was concerned about what would happen to their college-age son if they retired and lost their health coverage, given his pre-existing condition. Another was wondering specifically about tax mitigation in retirement.

All had valid questions, yet different needs to fill by seeking retirement. This is why we ideally recommend starting to plan for retirement at least 2 years before the year you expect to retire. This allows you to consider all your different life factors, along with your account balances.

Some really were not clear on what they are spending now, while working. This is a critical place to start because how can you forecast asset longevity without knowing what your assets will need to cover?

Then, to forecast into retirement, your spending will vary based on what you want to do. Life will shift and change over a retirement lifespan, which may easily cover 30 years.

Looking at what you want to do in retirement is important. One couple I met had different priorities: one spouse was very clear that travel is their priority, while the other intended to keep working for as long as possible because of their love for their profession.

On one hand, how wonderful it is to love your work; on the other, it will limit your availability for travel.

If you’re within a few years of retirement (or even just starting to think about it), here are four practical ways to begin designing it intentionally and to fully consider retirement’s cost.

I love these because you become a researcher of your own life – gathering data.

1. Begin the Experiment – Don’t Wait

Don’t wait for a hard stop to test what retirement might feel like. Start small.

Consider:

  • Take a weekday off and structure it differently
  • Reduce hours if possible
  • Experiment with activities you think you’ll enjoy

You’re not committing, you’re experimenting.

2. Map Out What a “Good Week” Looks Like

Don’t focus on “the rest of your life” at this point. Thinking about “the rest of your life” can feel abstract. Our brains are not wired for that. Instead, design a realistic, repeatable week.

Consider:

  • How do your mornings start?
  • Where does social connection happen?
  • What gives your days a sense of purpose?
  • If living with a partner or spouse, how are you sharing the home?

3. Identify What You’re Moving Toward

Some long to leave work – but that is not the whole picture.

Consider:

  • Relationships you want to deepen
  • Interests you’ve deferred
  • Ways you want to contribute, whether formal or informal
  • What you want to keep from your working years and use in your retirement years

Clarity here reduces the risk of feeling unmoored later.

4. Align Your Financial Plan with Your Life Plan

This is where the technical and personal sides of money come together.

Your financial plan should enable the life you’re envisioning.

Consider:

  • Timing of income and withdrawals
  • Flexibility for travel, health, or new pursuits
  • Capacity to adapt as priorities evolve

The question isn’t just:

  • “Will it last?” but also:
    • “Does it support the life I actually want?”
    • “Will it allow me to try things out and test my hypothesis of what I think will work well for me, my spouse, and family, without taking on too much risk?”

The best transitions into retirement are made before one retires. They’re designed thoughtfully, gradually, and with intention.

Retirement isn’t just a financial milestone, where one is working one day and then not the next. It’s a life transition.

YOUR life transition.

And, as such, it deserves quality attention so that the effort of your working years, and all you put into your career, creates a joyous shift into satisfying and interesting days, weeks, months, and years.

At Gates Pass Advisors, our philosophy is that there are two sides to effective financial strategizing. 

One is personal; the other is technical; BOTH are essential. 

While your financial plan technically clarifies and supports your transition to retirement, your life decisions, purpose, relationships, routines, and fulfillment are what ultimately define the experience.

We have tools to help inspire ideas if you draw a complete blank about what might be next. That is why we see ourselves as advisors and thought partners to our clients, helping them navigate this important life transition. 

Esther Szabo