Jeff Bowers, CFP® · Plan2Retire

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The Anti-Regret Playbook: Lessons from Those Who've Been There

Are you making intentional moves for the retirement you want?

Most people don't realize how much small decisions, like when to claim benefits or how long to keep working, can shape their future freedom.

That's why so many retirees look back and say, "I wish I had planned that differently."

This short playbook helps you avoid the same mistakes.

Inside, you'll find some of the most common regrets people have in retirement, reframed into clear, proactive moves you can make right now.

It's your financial game plan for the years ahead.

Simple, strategic, and built to help your future self breathe easier.

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Proactive Retirement Moves to Make Now

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Save on Schedule

Saving often takes a back seat. Retirement feels far away, and there's always a bill, a trip, or a repair that feels more urgent. But many retirees say their biggest regret is not starting sooner.1 Here's why: if you save $1,000 a month starting at age 40, with a 7% return, you could potentially have a ~$758,000 nest egg by age 65.* Start at 50, and you'd need to save ~$2,520 a month to reach a similar goal. That's the cost of waiting (in this hypothetical example). Start small. Automate it. The earlier you start, the more freedom you'll have to choose how your story plays out.

a starry night sky with a constellation of a chess piece

Time Your Benefits Strategically

Many people claim Social Security early out of fear, then wish they'd waited. Claiming at 62 locks in a smaller payment for life, while waiting until 70 can raise monthly benefits by about 32%.2 Delaying won't be right for everyone, but the right timing can turn patience into lasting peace of mind.

a starry night sky with a constellation of a alarm clock

Put Debt on a Deadline

Many retirees regret carrying debt into their later years. It shrinks their options and limits what they can enjoy. Every payment toward interest is one less toward freedom. Consider this approach: Pick a payoff date. Automate extra payments. Every balance you clear may increase your financial flexibility in retirement.

a starry night sky with a constellation of a medical cross

Decide Long-Term Care on Purpose

Nearly two-thirds of adults over 50 mistakenly believe Medicare will cover nursing home costs. Most haven't named a medical power of attorney or identified who could care for them.3 That's why long-term care often becomes a crisis instead of a choice. Planning ahead isn't just about care. It's about protecting choices, dignity, and the people who matter most.

a starry night sky with a constellation of a split path

Extend Optionality

Some retirees wish they had worked a little longer, not for the job itself but for the freedom it gave them later. It's not the right play for everyone, but even part-time work can stretch savings and reduce pressure. Think of it as adding time to the game clock. Flexibility now can ease the pressure when life throws a surprise play.

a starry night sky with a constellation of a briefcase

Play an Active Role in Your Career

Some retirees don't just regret their income. They regret the path they stayed on. Many were pushed out of the workforce before they were ready.4 They stayed too long in stalled roles, didn't learn new skills, or failed to grow their network. So keep moving forward. Upskill, network, stay ready. Staying engaged and prepared can help protect against career surprises.

a starry night sky with a constellation of a palm tree

Enjoy the Good Stuff

Some retirees say their biggest regret wasn't financial. It was waiting too long to enjoy life. Travel, adventure, even simple experiences became harder as health issues crept in.5 The lesson? Don't delay the moments that matter. Build a plan that lets you live fully today while still protecting tomorrow. Your best memories shouldn't be on hold.

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Consider Professional Guidance

Many retirees regret going it alone. Some underestimated how much of a nest egg they'd need. Others claimed benefits too early or didn't prepare for losing a spouse. Missed details like RMD rules, survivor benefits, or how withdrawals are taxed, can quietly erode your plan. But you don't have to do it alone. Professional guidance can turn complex choices into confident moves toward the life you want.

The relief of having a plan far outweighs the discomfort of making one.

Start Now

What would your future self thank you for?

Whether retirement is years from now or already underway, there's still time to make meaningful changes.

Maybe it's finally automating those savings. Perhaps it's having that long-term care conversation you've been avoiding. Or maybe it's simply sitting down to map out when you'll claim Social Security.

Carving out time to plan feels like one more thing on an endless list. And confronting these decisions can feel uncomfortable in the moment. But having a documented plan that reflects your values and priorities isn't just paperwork. It's a roadmap that already moves you closer to the retirement you actually want.

The relief of having a plan far outweighs the discomfort of making one.

A few intentional plays now can help protect your freedom, reduce stress, and create more space for the life you want.

You don't have to tackle everything at once. Start with one decision. Build momentum from there.

Your next move matters. Make it count.

Sincerely,

    Jeff Bowers, CFP®

    Plan2Retire

    https://plan2retire.com

    (240) 329-3333

 

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Jeff Bowers, CFP®

Plan2Retire

Not receiving our newsletter?

Get insightful info on finances and more in your inbox every month with the

VISUAL INSIGHTS NEWSLETTER

Jeff Bowers, CFP®

Plan2Retire

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*Assumes consistent monthly contributions and a 7% average annual return, compounded annually. This is a hypothetical example for illustrative purposes. Actual performance will vary.

Risk Disclosure: Investing involves risk including the potential loss of principal. No investment strategy can guarantee a profit or protect against loss in periods of declining values. Past performance does not guarantee future results.

This material is for information purposes only and is not intended as an offer or solicitation with respect to the purchase or sale of any security. The content is developed from sources believed to be providing accurate information; no warranty, expressed or implied, is made regarding accuracy, adequacy, completeness, legality, reliability, or usefulness of any information. Consult your financial professional before making any investment decision. For illustrative use only.

This information is not intended to be a substitute for specific individualized tax advice. We suggest that you discuss your specific situation with a qualified tax professional.