Retirement in 10 years? If you’re 10 to 20 years from retirement, you’re in a powerful position: close enough to see the outline of your future, but with time to shape it meaningfully. At Boldin, we hear from thousands of users who’ve been through this stage—and many who are now on the other side of retirement, looking back with clarity.
We asked them what they wish they had done when they were in your shoes. Their insights are honest, practical, and sometimes surprising. Whether it’s financial moves they’d make earlier, mindset shifts they’d adopt, or blind spots they’d watch out for—this is the kind of wisdom you only get from people who’ve lived it
You can find lists of how to plan for retirement when you are 10 years away, but here are 15 lessons from people who have been in your shoes. Use these tips to plan smarter, live more intentionally, and make the most of the next decade.
1. Think You’re 10 Years from Retirement? You Might Be able to Retire Earlier!
“I would have retired sooner. It seems I over saved.” – Brad
Over-saving might sound far fetched, but it’s a common thing. At Boldin, we regularly see subscribers who are in far better shape than they think. They’ve been diligent savers, made smart financial choices for decades, and now have strong portfolios and manageable expenses—but they’re still grinding away at full-time work out of habit or uncertainty. Often, it’s not a lack of money that’s keeping them working. It’s a lack of clarity.
If you are 10 years from retirement, you should pause to run the numbers or consider what your savings can actually do for you. Too many people are still operating on the same scripts—save more, work longer, be safe—that served them well earlier in life. But those scripts don’t always adapt to the reality of financial independence. And for people who aren’t enjoying work as much as they used to, that inertia can be costly—not just in time, but in energy and missed opportunities.
Take control of your money and time: Use the Boldin Retirement Planner to break the keep working cycle. By running a personalized retirement plan and modeling different timelines, you can see whether you’ve already crossed the finish line—or if it’s closer than you think. Taking a hard look at the data can give you permission to explore other options: going part-time, taking a sabbatical, or even retiring sooner than you ever imagined.
2. Treat Your Partner Right
“I should have spent a lot more time working on making my marriage better every day. Lots of us end up divorced in our 50’s, shortly after the kids leave home. That’s the biggest emotional and financial collapse that can happen to even the best retirement planning.” – Jeffrey
One of the most overlooked parts of retirement planning is your relationship. As kids leave home and the pace of life shifts, many couples find themselves drifting apart, sometimes leading to divorce just as retirement comes into view. Beyond the emotional toll, divorce in your 50s can upend even the most carefully built financial plans. That’s why investing time and care into your partnership isn’t just good for your heart—it’s good for your future stability. A strong relationship can be your greatest asset in the decades ahead.
Here are 10 essential conversations planning conversations for a happily ever after.
3. Be Ready for a Forced Retirement
“Make sure you have a giant pile of F You money. 50% of people over 50 end up getting downsized. My giant pile allowed me to retire early.” – Jenn
“What I could have planned better for was a forced retirement. Many people are forced to retire earlier than they plan to. Maybe I could have trained for something else, or switched jobs to somewhere else, earlier to make the change easier and more on my terms. But whatever, I guess I’ll just have to enjoy being retired.” – Glenn
No matter how carefully you plan, retirement doesn’t always happen on your terms. If you think you are 10 years from retirement, be aware that health issues, company layoffs, or ageism in the workplace could push you out of the workforce earlier than expected. In fact, nearly half of workers over 50 experience some form of involuntary job loss, and many never regain their previous income. Learn more about forced retirement.
4. Roth. Roth. Roth. More Savings to Roth
Of all the responses, a huge majority recommended various strategies involving Roth accounts. Here are just a few of the comments:
“[I recommend saving] more to Roth, less to traditional, even in my so-called ‘high earning years.” – Kelly
“I should have found out about Roth IRAs a lot sooner and put the max in each year. They were invented well after I started working and all my employer offered was a 457b. Now in the process of converting the 457b to my Roth, which I thankfully opened my last two years of employment.” – Rob
“I would have invested for retirement in this order: 401k (but only up to match), Roth (max allowed), brokerage.” – Carolyn
“More Roth! Less traditional IRAs.” – Shirley
“Would have put more in my Roth.” – Karen
“I would have used Roths to avoid a tax time bomb.” – Jeannine
“I assumed our taxes would be lower in retirement. Not exactly….. especially when trying to convert to Roths. You have to plan this carefully for taxes.” – Diane
For many people, the default approach is to prioritize traditional 401(k) or IRA contributions during their peak earning years, assuming they’ll be in a lower tax bracket in retirement. But that’s not always how things play out. Why? Because Roth contributions are made with after-tax dollars, and they grow tax-free—so when you withdraw in retirement, you owe nothing on that money.
This kind of tax diversification can create powerful flexibility in retirement. By building up both Roth and traditional accounts, you give your future self more control over taxes, withdrawals, and even things like Medicare premiums and Social Security taxation.
Having a healthy Roth balance can also make it easier to:
- Do Roth conversions later. (Having a Roth IRA already open means your 5-year clock is likely running—this is the IRS rule that requires Roth funds to be held for at least five years before earnings can be withdrawn tax-free—giving future Roth conversions more flexibility and faster access to tax-free withdrawals.)
- Fill in income gaps without triggering extra taxes.
- Delay tapping taxable accounts.
Use the Boldin Retirement Planner to see what’s right for you: Run a “what if” scenario where some or all of your contributions go into a Roth account. Compare outcomes with all savings going to a traditional account.
5. Do a Mega Backdoor Roth
“Mega back door Roth if you can. In my company it wasn’t ‘advertised.’ I wish I’d known about it sooner.” – Amy
The Mega Backdoor Roth allows high earners to contribute significantly more to Roth accounts than the standard Roth IRA limits by using after-tax 401(k) contributions and converting them into a Roth 401(k) or Roth IRA.
Why does this matter? In retirement, minimizing your taxable income can reduce Medicare surcharges, avoid triggering taxes on Social Security benefits, and create more room for strategic withdrawals or Roth conversions. By building up a large Roth balance now, you’re essentially pre-paying taxes at today’s known rates and giving yourself a future stream of tax-free income that won’t push you into higher brackets later. This flexibility becomes especially valuable if you’re considering retiring early or spacing out income over time.
Starting a Mega Backdoor Roth strategy early gives you the benefit of compounding over more years, and it starts the 5-year clock for tax-free withdrawals on conversions. Even if you’re not sure whether you’ll use the Roth balance right away, having it in place gives you more planning options. If your employer’s plan allows it—and not all do—it’s well worth exploring this move while you’re still earning a high income.
6. Retire Early and Use Roth Funds to Help Cover Medical Costs Before You Are Eligible fo Medicare
“I would have socked away more non-IRA/401(k) funds. If you can live off funds in your late 50s that have already been taxed then you can qualify for incredible ACA subsidies prior to Medicare.” – Marshall
Healthcare can be one of the biggest wildcards in early retirement, especially if you leave work before Medicare eligibility begins at age 65. Many people overlook how powerful tax-free withdrawals from Roth accounts (or other after-tax savings) can be during this transition. If you can keep your taxable income low in your late 50s and early 60s, you may qualify for substantial subsidies on ACA health insurance plans, sometimes saving thousands per year.
That’s where Roth accounts come in. Because Roth withdrawals generally don’t count as taxable income, they can help you cover living expenses, including health insurance, without pushing you into a higher income bracket. Planning and building a healthy Roth balance—or setting aside after-tax savings—can give you more flexibility, help you bridge the gap to Medicare, and reduce the strain of unexpected medical costs in early retirement.
7. Max Out Tax-Advantaged Retirement Savings – Roth and Traditional
“More savings and take advantage of Roth.” – Van
“Would have maxed out both of our Roths every single year.” – Maxing out your tax-advantaged retirement accounts—both Roth and Traditional—is one of the smartest moves you can make in the years leading up to retirement. In 2025, if you are 50 or over, you can contribute a whopping total of $39,000 (double that if you are married and both qualify) into IRAs and 401ks. These accounts offer powerful tax benefits that help your money grow more efficiently than in a regular savings or brokerage account. (Learn more about catch-up savings.)
The advantage comes down to taxes: Traditional contributions lower your taxable income today, while Roth contributions grow tax-free and can be withdrawn tax-free in retirement. Either way, you’re shielding your investment gains from annual taxes, which means your savings compound faster. By consistently maxing out these accounts, you not only build wealth, you also give yourself more flexibility and control over how and when you pay taxes in retirement.
8. Be Creative About Family Expenses
“If I’d had a crystal ball, I would’ve bought a condo for my college daughter to live in as a freshman rather than paying rent for 4+ years (mortgage rates were 3% back then and condos cheap).” – Tara
As you approach retirement, family expenses don’t always go away—they often shift. Many Boldin subscribers in their 50s and early 60s find themselves sandwiched between supporting aging parents and launching young adult children. That phase can feel financially overwhelming, but it also presents opportunities to make smarter, more creative long-term choices. Take housing, for example: instead of paying rent for a college-age child, some people choose to invest in a modest property—potentially building equity while supporting their family.
Similarly, helping a parent downsize, manage care costs, or sell a long-held home can create emotional and financial complexity. But with thoughtful planning, these life transitions can also open up options, like shared housing, multigenerational living, or reallocating family resources to reduce future financial strain. The key is to step back, look at the big picture, and treat family expenses not just as obligations—but as planning decisions that can either strengthen or weaken your own retirement readiness.
9. Plan (and Act) Early for the Life You Want
“The only thing I would’ve done differently is look for and buy a property where I knew I wanted to spend my retirement (in my case, a mountain cabin/home). Rent it out for income until I got there. I am retired (early and on my terms) but am searching for that cabin now. I wish I just had it and I was writing to you from the front porch drinking coffee.” – Jen
Too often, we treat retirement like a switch we’ll flip someday, without preparing for the life we actually want to live once we get there. But many Boldin users say they wish they had made those lifestyle dreams part of the plan sooner. Whether it’s a mountain cabin, a coastal bungalow, or a condo in the city, buying a future retirement home early can serve multiple purposes: it locks in housing before prices rise, creates a potential income stream through rentals, and lets you test-drive your dream before making it permanent.
If you are 10 years from retirement, it is time to act. You’re not just planning for retirement—you’re actively designing it. If you know where you want to end up, consider modeling the purchase in Boldin. You can track the impact of rental income, mortgage costs, and long-term appreciation to see how the decision fits into your broader financial picture. More than just a financial move, it’s a way to align your money with your vision—so one day, you’re not just dreaming about coffee on the porch, you’re living it.
10. Take Advantage of Your Relative Youth
“More travel when younger. Even though we were always active, things like knee replacements plague us now in our 60s. I can’t hike and do what I want to anymore.” – Janine
“I would have traveled more. I bought used, lived below my means, tracked expenses, stuffed my Roth, 401K, and even had a side hustle. But I didn’t go on enough adventure vacations while I was still agile & daring.” – Sharissa
Many Boldin users say they were so focused on doing everything “right” financially—saving diligently, living below their means, maximizing their Roths and 401(k)s—that they missed out on something priceless: youthful adventure. Travel, exploration, and physical challenges often get put on the back burner in the name of frugality, but time has a way of changing what your body can do—even if you’ve always been active.
Mobility, energy, and a spirit of daring are resources, too—and they don’t always last as long as your retirement savings. If there are places you’ve dreamed of hiking, cultures you’ve longed to explore, or adventures you’ve imagined taking, consider building them into your plan while your knees (and curiosity) are still strong.
Plan Your Dreams: With the Boldin Planner, you can model early travel goals right alongside your long-term financial needs. It’s not indulgent—it’s intentional. Because sometimes the best return on investment is the memory of a mountaintop you were brave enough to climb.
11. More Investing Awareness and Know How
“I would have opened a Roth IRA, and an investment account.” – Billy
“I did too much of target date stuff… I would have done VTI or VOO type allocation. I also didn’t really think through my taxable non-retirement stuff.” – Tim
“Max out everything. Dollar cost average. Hope for a financial downswing so you can invest on the way down and the way up.” – Bob
“I wish I better reacted to the 2000 start of the secular bear market, although I was all in on stocks when the secular bull started in 2009. I wish I kept up with new types of investments/funds. Knowledge of long/short ETFs and Momentum funds would have changed my portfolio a bit. All of these fall under doing more research about.” – Larry
Several Boldin users say they wish they had gained more investing knowledge earlier—not just about how to invest, but what to invest in and where to hold those investments. For some, that meant opening the right kinds of accounts, like a Roth IRA or a taxable brokerage account. For others, it meant thinking more critically about their investment choices—beyond defaulting to target date funds—and exploring broader options like index funds (VTI, VOO), long/short strategies, or momentum-based funds.
Others wish they had been more proactive during market downturns, viewing volatility as a long-term opportunity rather than something to fear. Strategies like dollar-cost averaging and continuing to invest during downturns are easier to follow when you understand the bigger picture and have a plan.
The takeaway? It pays to stay curious, expand your toolkit, and periodically revisit whether your portfolio and account structure are aligned with your goals.
12. Get a Side Hustle
“Have a side hustle when younger to save more and retire earlier.” – Janine
Adding a side hustle in your younger years can be a powerful accelerant to your financial goals. Whether it’s freelancing, tutoring, selling goods, or building a small business, that extra income can supercharge your savings, help you max out retirement accounts, or give you the freedom to retire earlier. It’s not just about the money—it’s about building flexibility and optionality into your future. Learn more about passive income.
13. Exercise, Do Weight Training
“More exercise, especially weight training.” – Rhonda
Staying strong pays off—literally. Regular weight training in midlife can improve mobility, prevent injury, and reduce long-term healthcare costs. As Rhonda’s advice suggests, investing in your physical strength now can help you enjoy retirement with more energy, freedom, and confidence.
14. Economize
“I would have paid off bills sooner. Buy gently used instead of new cars. Get rid of the credit card balances or not accumulate them at all. I would have had a lot more to invest. (But we are doing fine after retiring at 55, and my husband at 63.)” – Sandy
Whether you are 10 years from retirement, of 50, no financial strategy is complete without a healthy dose of frugality. As Sandy points out, avoiding debt, buying used, and living below your means can free up thousands for investing and early retirement. While it’s easy to focus on tax strategies or investment hacks, consistent economizing is often the quiet engine behind long-term financial success. It’s not flashy—but it works.
15. Get an HSA
“I wish I had started an HSA sooner. As soon as they became a thing.” – Alisa
A Health Savings Account (HSA) is one of the most powerful, underutilized tools for retirement planning. If you’re enrolled in a high-deductible health plan, you’re eligible to contribute—and the benefits are hard to beat: contributions are tax-deductible, growth is tax-free, and qualified withdrawals for medical expenses are also tax-free. That’s a triple tax advantage.
Many Boldin users, like Alisa, wish they had started earlier. Why? Because HSAs aren’t just for current medical bills—they can double as a stealth retirement account. After age 65, you can even use HSA funds for non-medical expenses (you’ll just pay regular income tax, like a traditional IRA). So whether you’re saving for future healthcare or just want more tax-advantaged space, an HSA is a smart move that can quietly build financial flexibility for the long haul.
16. Retirement in 10 Years? It is Time for a Written Plan!
“We played the game pretty well, but there is always room for improvement. Using Boldin or something similar before I retired would have been advantageous.” – Larry
Even when you’ve made smart decisions along the way, having a clear, written financial plan when you are 10 years from retirement can be a game-changer—something many current Boldin users realize in hindsight.
The Boldin Planner is designed to help you create that plan—one that balances today’s priorities with tomorrow’s goals. It gives you a clear picture of how your spending, saving, and investing decisions impact your long-term success. Whether you’re deciding when to retire, how much to spend on travel, or whether you can support a family member, Boldin helps you model it out and make decisions with confidence. A written plan doesn’t just chart a path to retirement—it gives you the clarity to live your life on purpose, every step of the way.
About Boldin
Boldin is democritizing access to high quality financial planning and helps real people build plans they understand and trust. Our intuitive Retirement Planner software puts you in control of your future—while our coaching, classes, and access to expert advice from CFP® professionals at Boldin Advisors ensure you don’t have to do it alone. Whether you’re planning for retirement, navigating life transitions, or just trying to make smarter financial decisions, Boldin combines clarity, confidence, and affordability to help you move forward with purpose.