Are you nearing retirement? Few life transitions are bigger than this one. The question on everyone’s mind: how do you make sure it’s not just possible, but truly sustainable and fulfilling?
If you want to know how to retire, here are 19 important things you should do as you approach the big date to ensure a happy and secure future:
1. Create, Maintain, and Evolve Your Retirement Plan
It may sound obvious, but if you’re nearing retirement, a detailed plan is non-negotiable. A good plan maps your resources, goals, and risks so you can step into retirement with clarity and confidence. And once you’ve retired, it’s not a “set it and forget it” exercise — reviewing and adjusting every few months keeps your plan aligned with life as it changes.
The research is clear. People who feel that they have control over the retirement process have better outcomes in retirement. However, Gallup Polls found that only 43% of retired investors and a mere 36% of non-retired investors have a written financial plan.
Do you really want to wing it in retirement and risk running out of savings completely? The Boldin Retirement Planner makes it easy to create and maintain a holistic retirement plan. This tool is named a best retirement calculator by Bankrate, US News and World Report, the American Association of Individual Investors (AAII) and many others.
2. Stop Worrying, Take the Leap of Faith, and Retire!
It’s normal to feel anxious in the years leading up to retirement — research shows stress is at its peak just before you step away from work. But here’s the good news: once people retire, most report feeling happier and more satisfied than they expected. Those who planned thoroughly feel especially confident, yet even those less prepared usually find ways to make it work.
In fact, studies show optimism soars in your 60s — a decade when lifelong happiness often peaks. While you can’t predict every twist ahead, a flexible retirement plan helps you weather the unexpected and stay on track. So prepare well, trust your plan, and give yourself permission to take the leap.
3. Celebrate!
Retirement is a big reason to celebrate (especially if you have prepared a responsible plan)! Throwing a party to commemorate the occasion can be a wonderful way to launch the next phase of your life.
Get tips for planning a retirement party.
4. Find a Cause
Having meaning in your life is a critical component of happiness. Many people find purpose in their careers. When you retire, it is important to identify a new purpose for your life.
You don’t need to save the world; any cause, large or small, can help you maintain your vitality.
Whether you opt to work full-time on a single cause, volunteer once a week, or just adopt a pet, whatever you do should give you personal satisfaction. When thinking about purpose, think about what kind of legacy you want to leave to your community.
Here are a couple of resources to help you identify your retirement cause:
5. Gussy Yourself Up for Your New Life
Retirement is not a time to fade into the woodwork. Retirees these days see retirement as a new beginning, so it is an ideal time to freshen up. Your old look might not be compatible with your new life.
Whether a makeover means a new pair of running shoes or a head-to-toe remake is up to you. Clean out your closets, donate what you no longer need, and make sure you are suited for your new activities.
Think about a new retirement wardrobe, haircut and sense of self.
6. Really Imagine Your Future
If you want to know how to retire well, perhaps the best thing to do is to visualize your future — really think about the details of who you will be, where, and why. Being able to imagine now who you will be in the future and what your needs and desires will be at that time is perhaps the most important aspect of planning.
Here are 7 exercises to help you visualize your future.
7. Try 3 New Things
One of the greatest gifts of retirement is freedom. With more time and fewer constraints, many retirees describe this stage of life as a chance to rediscover curiosity and optimism. It’s the perfect moment to step outside your routine and try something new.
New experiences aren’t just fun — they keep life fresh, fight boredom, and push you to grow in ways you may not have expected. My mom recently signed up for dancing and acting classes, and I swear she carries herself with a new spark in her voice and energy in her step.
Science backs it up: learning new skills strengthens brain function, supports better health, and can boost your vitality for years to come. Whether it’s joining a book club, exploring pickleball, tackling a creative hobby, or traveling somewhere new, challenge yourself to try at least three new things. You may be surprised by how much joy and resilience they add to your retirement.
8. Set a Goal
Having a goal is a good way to make sure that your life is organized in a positive way.
Your goals do not necessarily have to be important, just satisfying to you. Set goals for improving your golf score, seeing grandchildren, smiling at people, watching less TV.
As you are nearing retirement, you are probably asking how to make travel a big part of your life. Travel is the most popular retirement goal. Here are 20 great ways to make travel part of your retirement.
9. Plan Big Purchases
Will you need a new car? Are you hoping to go on a big trip or buy a boat or RV? Do you want to try to contribute to your grandchildren’s education? Are you buying a fishing cabin?
Work these big purchases into your overall retirement plan. The Boldin Retirement Planner enables you to document as many different future big purchases as you can imagine. You can also create a highly detailed monthly budget – reflecting current and future spending.
10. Consider Your Social Security Start Age Carefully
No matter if you are retiring at 62, 55, or 72, you don’t have to start Social Security when you leave the workforce. In fact, the longer you wait, the more your monthly benefit will be. Use a Social Security calculator (part of the Boldin Planner) to figure out the best time to start this benefit. Or, learn more about when to start Social Security and how to apply.
11. Make Sure Your Healthcare Needs Are Covered throughout Your Life
Even with Medicare, healthcare is going to be one of your biggest expenses in retirement. The Boldin Planner will help you estimate these costs, but here are a few tips:
Medicare: At age 65 you become eligible for Medicare and you’ll want to choose the best supplemental plan for your needs. It can be a big confusing decision, but you can re-evaluate it every year during the open enrollment period.
Retiring before Medicare eligibility?: An early retirement can mean significant insurance costs. Explore 9 ways to afford healthcare before you turn 65.
Long-term care: Don’t forget that your healthcare costs may skyrocket near the end of your life due to a long-term care need.
12. Simplify Accounts
Juggling multiple retirement accounts can get messy — and costly. As you are nearing retirement, consider consolidating your savings. It can cut down on fees, streamline your investments, and make it easier to see the full picture of your retirement plan.
If you do combine tax-advantaged accounts like 401(k)s or IRAs, be sure to use the proper rollover process. Done right, it’s a clean transfer; done wrong, it could trigger unnecessary taxes and penalties.
13. Write or Edit Your Investment Policy Statement
An Investment Policy Statement (IPS) is a written document, usually but not necessarily prepared by a financial advisor. It covers your investment goals, your strategy for achieving those goals, a framework for making changes to your plan, and options for what to do if things don’t go as expected.
As you move from asset accumulation to turning your savings into retirement income, shifting your investment strategies is an important aspect of “how to retire.”
Learn more about the Investment Policy Statement.
14. Prepare for a New Routine
After retirement, there’s nothing but time, so it might seem that schedules aren’t crucial. But a routine might be as important as ever, and for several different reasons.
Routines help us stay productive and get things done. We do things that are routine out of habit, and the fact that you don’t really need to think about it reduces stress. Routines are a good foundation for enabling you to be creative. In fact, routines have been proven to increase health and psychological well-being.
In your first year after retirement, it is especially important that you try to establish healthy routines. Whatever else you include in your routine, be sure to include exercise. Exercise is a critical component of a happy and healthy retirement, and once it becomes routine, it is a true joy. Whether it is daily gardening, a walk around the block or training for a marathon, just make it part of what you do every day.
15. Clean Out the House or… Relocate
Our homes are usually set up to accommodate our lifestyles. In retirement, life changes pretty dramatically. You will want to first assess whether or not where you live is ideal for what you want out of retirement. If it isn’t, consider downsizing or relocating to a best place to retire.
If you love where you live, consider taking a sweep through the house to clean up and get rid of things you no longer need.
KonMari was a trend that “swept” (yes, bad pun intended) the nation. It is a charming approach to organizing and paring down your belongings in an ultimate quest for joy. Death cleaning is a perhaps more morbid way of talking about cleaning out closets. Here are 7 reasons to de-clutter in retirement.
15. Get a Check Up
Meeting with your doctors as you near retirement is a great way to kick off your future. Discuss ways to stay healthy, get your flu shot, and create a plan for aging.
16. Create a Plan for Eating Well, Staying Physically Active and Maintaining Good Health
Studies show that good physical health is associated with a range of positive outcomes in retirement, such as life satisfaction and quality of life.
Keys to good health involve regular check-ups with your physician as well as:
Regular physical exercise. You don’t necessarily have to lift weights or go on five-mile runs. According to Dan Buettner, author of “The Blue Zones: 9 Lessons for Living Longer from the People Who’ve Lived the Longest,” the longest living people in the world make movement a natural part of their everyday life. They move in meaningful ways about every 20 minutes, and walking is their primary mode of transportation.
Eat well: It seems like dietary guidelines are changing all the time. So, maybe stick to what has been discovered by Buettner. His recommendations include that 95% of your food be plant-based, stop eating when 80% full, and include beans and nuts in your daily diet.
17. Create a Social Community
Having friends and seeing them on a regular basis is an important way to stay healthy and engaged. However, staying social can be more difficult after retirement.
Meeting up with people takes a little more effort since it is not automatically part of a routine, as it is when you are working.
As such, you will want to prepare for retirement by creating social habits. Arrange to meet with friends for coffee each morning. Join a club. Find a volunteer or part-time job opportunity. Whatever you do, be sure to make it a habit and something where you will be held accountable.
Technology is making it easier and easier to stay at home. However, to retain your mental and emotional well-being, you need to make regular physical contact with others.
Discover why loneliness is a significant risk to your health.
18. Make Sure to Think Through Financial Obligations to Your Kids (and Parents)
Currently, record numbers of 18-34 year olds are living with their parents. These children can often be a financial burden. Your own parents might be another potential expense that you will need to budget. Will they need financial assistance? Will you need to care for them as they age?
When you retire, you need to assess all kinds of expenses, including family.
19. Learn About Retirement Taxes
Taxes are often overlooked when it comes to retirement planning. First, how you pay taxes will change since they will no longer be withdrawn from your paycheck. But, more importantly, many retirees underestimate this expense.
As you near retirement, use the Boldin Planner to evaluate your future tax burden and discover ways to reduce the expense. And here are 25 retirement tax tips.
The Bottom Line
As you near retirement, creating a robust written plan for your finances is essential — but money is only one part of the picture. What truly matters is building a life that feels meaningful, secure, and aligned with your goals.
We hope this checklist inspires you to take action, prepare thoughtfully, and embrace retirement with confidence. Plan well, live fully, and give yourself the freedom to enjoy the years ahead.