The No-Regret Retirement: 16 Ways to Plan for a Life of Freedom and Confidence

A no-regret retirement is one of life’s biggest decisions. It’s a major transition — not unlike choosing a career, a partner, or where to put down roots — and it deserves the same level of thought and care.

The difference is that retirement isn’t a single choice. It’s a series of decisions about money, time, purpose, and flexibility. The good news is that even if you’ve already retired — or feel close to taking the leap — it’s never too late to reduce regret and increase confidence.

Below are a few practical ideas to help you plan — or refine — a retirement you can feel good about.

1) Focus on Your Plan to Spend Time with People – Especially People You Love

Love, it is what makes the world go round, and it fuels almost everything, including retirement.

And love is all about people. Study after study has shown that people on their deathbeds most regret not spending more time with friends and family.

One such study from Northwestern University found that regrets about relationships represented 43% of the survey respondents, well exceeding the 35% of people who cited work or financial concerns.

2) Retire at the Right Time – Not Too Late or Too Early

Lots of people retire only to find that they are unhappy or worried. Others retire and are so happy they can’t believe that they didn’t do it sooner.

If you aren’t sure about when to retire, you might benefit from some professional advice.

Lifestyle concerns: If your concerns about when to retire are related to lifestyle issues – knowing what to do in retirement, trying to figure out if you will be happy with your decision – then you might benefit from working with a therapist or talking with friends.

Financial worries: If you have financial concerns, you have options. Start by building a comprehensive plan and assessing where you stand. The Boldin Retirement Planner can help you get organized and it will identify opportunities for doing better.

Validating your plan with a coach or getting insights and advice from a financial advisor is another way to build confidence and discover how to retire securely.

3) Don’t Put Off What You Really Want to Do – Travel While You Can!

Travel is the number one goal for most retirees. A full 90% of Boldin Retirement Planner users mention travel as one of their goals. However, whatever it is you want to do, do it. Do it sooner rather than later!

We don’t always want to face it, but the reality is that the clock is ticking. Now is the time to achieve your goals.

If travel is what you want to do, here are tips for satisfying your wanderlust at any budget. Not sure how you want to spend your time? Here is a list of 120 things to do in retirement.

4) Build a Really Detailed Retirement Plan

I know you have heard this one before, but it is important. If you want a no-regret retirement, you need a really detailed plan.

In some ways, retirement means you are flying without a net. You are living off what you already have. And, unless you go back to work, you have to make your existing resources last as long as you do, no matter how long that turns out to be.

You don’t want to retire with just a vague guess about how you are going to pay for everything. That is stressful.

To feel confident with your ability to fund your (and your spouse’s) retirement, you will be well served by creating a really detailed plan. You want to be able to see how you are going to make ends meet over the next 20 or 30 years!

The Boldin Retirement Planner is the best way to get your hands around this gargantuan task. It is an easy step-by-step approach to creating a plan, understanding where you stand, finding ways to make it better, and maintaining it over time.

5) Plan for the Most Common Financial Surprises

Even people who plan carefully are often surprised by how different retirement finances feel in practice. Some of the most common financial regrets don’t come from saving too little — they come from misunderstanding how money actually works in retirement.

A few realities that often catch people off guard:

Taxes don’t disappear (In fact, they might increase)

Many retirees are surprised to learn that taxes can remain a meaningful expense — especially when withdrawals, Social Security, and required minimum distributions overlap. Without planning, income can bunch up in ways that increase lifetime taxes.

Use the Boldin Planner to strategize lifetime taxes and Roth conversions.

Spending isn’t linear

Retirement spending often comes in phases: higher early on (travel, experiences), lower in mid-retirement, and potentially higher again later due to healthcare needs. Planning for a flat spending number can lead to unnecessary anxiety or missed opportunities.

Markets matter more at the beginning of retirement

The early years of retirement are especially sensitive to market downturns. Poor returns early on can have an outsized impact on long-term security, which is why stress-testing plans matters so much.

Healthcare costs Are real — and uneven

Healthcare and long-term care expenses don’t hit evenly. They tend to arrive later, and often suddenly. Planning for them reduces both financial and emotional stress.

A no-regret retirement isn’t about predicting the future perfectly. It’s about understanding these realities early, testing different scenarios, and making informed tradeoffs — so surprises don’t turn into setbacks.

6) Go Beyond the Numbers and Envision the Future You Want

It’s easy to think of retirement as a financial finish line. But money is only the foundation — not the experience itself.

Many people spend years preparing financially for retirement, only to discover they haven’t really thought about what daily life will look like once work is no longer structuring their time. A no-regret retirement starts with imagining the life you want to live, not just the balance you want to see.

Ask yourself:

• What does a typical day look like?
• Where do you want to live — and how might that change over time?
• How do you want to spend your time, energy, and attention?
• What activities give you a sense of meaning or momentum?

When you take time to envision your retirement lifestyle, financial planning becomes more concrete. You’re no longer saving or spending in the abstract — you’re planning for a life you can picture, shape, and look forward to.

7) Keep Your Plans Updated and Make Adjustments

You can’t plan for everything. What you can do is update your plans monthly or quarterly. Just check in, document what has changed, make sure you are on track, and adjust as necessary.

8) Retire When You’re Ready for the Freedom

Ask retirees what they love most about retirement, and one word comes up again and again: freedom.

In a study by the Transamerica Center for Retirement Studies (TCRS), people most often described retirement as “freedom” (55%), followed by “enjoyment” (53%) and “stress-free” (43%). That sense of freedom is a big part of the dream — even though getting there takes real planning and effort.

But freedom feels good only when you’re ready for it.

If you have kids, you may remember saying some version of this: “With freedom comes responsibility.” The same idea applies to retirement.

A no-regret retirement isn’t just about having enough money to stop working. It’s about being prepared to manage the freedom — financially, emotionally, and socially. That means understanding your spending, feeling confident about your income, and having a sense of how you want to use your time.

The goal isn’t to retire as early as possible. It’s to retire when you can enjoy the freedom without second-guessing it.

9) Maintain Your Health

If you are already in your late nineties, maybe it is okay to go ahead and smoke cigarettes, eat all the cupcakes, and enjoy whatever bacchanalian delights you desire. Those vices will probably take longer to kill you than any natural occurrence.

However, if you are any younger, you might as well take care of yourself – eat well, exercise, and keep your brain active – so that you can really enjoy life.

Remember, “don’t ever regret getting old, many are denied the privilege!”

10) Speaking of Death, Think About Your Death!

What? Yes, you read that correctly.

An essay published in the New York Times made the case that thinking about your death can make you happier. The idea is to think about your daily choices as if this year were your last year. The research indicates that using death to help prioritize how you use your time actually improves your satisfaction and overall happiness with your choices.

And if you are worried that thinking about death is too depressing, the opposite may be true. Researchers have found that contemplating mortality can actually make you funnier — “Joking in the face of death: A terror management approach to humor production.”

11) Be Ready to Shift to New Identities and Purposes

Retirement is often described as a financial milestone, but it’s just as much a psychological transition.

For decades, work may have provided structure, identity, social connection, and a sense of purpose. When that suddenly disappears, even a well-funded retirement can feel disorienting. This is one of the most common — and least discussed — sources of retirement regret.

Many retirees report being surprised by:

• A loss of identity after leaving a long career
• Feeling unmoored without clear goals or routines
• Missing the social connection work once provided

A no-regret retirement means planning for this transition, not just the date on the calendar. That might include:

• Gradually shifting into retirement through consulting or part-time work
• Creating new routines and commitments before you fully stop working
• Investing in relationships, learning, or service that provide meaning
• Giving yourself permission to experiment — and adjust

Think of retirement as a transition

Retirement isn’t something you “get right” on day one. It’s a phase you grow into. The more intentional you are about the emotional and social side of the transition, the more likely retirement feels expansive rather than empty.

12) Get Rid of Stuff You Don’t Need – Even Your Home

You have probably heard the stories, the millennials don’t want your stuff.

Young adults today live in smaller houses, they buy used and are more into experiences than antiques, heirlooms, old desks, books or porcelain.

So, you don’t have to hold onto it all for them. And, you may emotionally benefit from cleaning it all out.

However, the real benefit of sifting through your stuff is not just the joy that Marie Kondo preaches, you may find that the upside is downsizing your home! Learn more about the benefits of de-cluttering.

Downsizing can be a good move for your retirement lifestyle and it is one of the most effective ways to boost your retirement finances.

13) Plan with Your Spouse

If you are married and don’t want to have a gray divorce, you might want to make sure that you plan retirement WITH your spouse.

It sounds obvious, but it happens far less often than you would think.

14) Don’t Start Social Security Too Soon

Want a no-regret retirement? Don’t start Social Security too soon. You can retire, just don’t start Social Security until you understand the lifetime value of your benefits.

According to the Social Security Administration, “We calculate your basic Social Security benefit — the amount you would receive at your full retirement age — based on your lifetime earnings. However, the actual amount you receive each month depends on when you start receiving benefits. You can start your retirement benefit at any point from age 62 up until age 70, and your benefit will be higher the longer you delay starting it.”

The difference between starting at 62 and starting at 70 can be around $100,000, maybe more, depending on spousal benefits!

15) Spend Early

A lot of retirees strive to plan a steady income stream for the remainder of their lives. This might not be the best idea.

The reality is that, for many people, retirement consists of different phases. You might spend more when you first retire, less as you start to slow down, not very much when you are old, and then really a lot for healthcare in the last year of your life.

Think carefully and budget for ebbs and flows in your spending, and you may feel better about a few splurges when you first retire.  Learn more about creating a reliable retirement budget and planning for evolving spending.

16) Consider Spending it All!

You earned retirement. You saved. You accrued benefits. If you want to spend it all, go for it! The Die with Zero retirement plan is compelling to many.

The Boldin Retirement Planner can help you find your max spending rate. You can also identify exactly how much you would like to leave behind and plan for that too.

A No-Regret Retirement Is Built Over Time

A no-regret retirement isn’t about perfect timing or flawless decisions. It’s about being intentional — understanding what matters to you, preparing for both the financial and emotional realities ahead, and giving yourself the flexibility to adjust as life changes.

The most confident retirees aren’t the ones who guessed right once. They’re the ones who kept learning, testing assumptions, and making informed choices along the way.

With the Boldin Planner, retirement planning doesn’t have to feel overwhelming. It can feel empowering — a way to turn uncertainty into insight and build a future you can step into with confidence.