In one of my other posts, “The coulda, shoulda, woulda behind every retirement story,” I asked for comments. Who better than soon-to-be retirees and recent retirees to share lessons learned about preparing for retirement, right? (Exactly right.)

The record-setting number of comments we received was amazing, but the comments themselves are what truly blew me away.

In this post, I provide an overview of what you had to say about what you “coulda, shoulda, woulda” done differently to prepare for retirement. But first, I want to thank you for sharing your stories with the community. And I want to congratulate you on retirement.

Getting an insider’s perspective is helpful to me as a financial advisor because everyone’s picture of retirement “success” is different. But seeing how thoughtful and resilient real-life investors are—moving forward after making missteps, making the best of any circumstance, and reflecting on their own journeys for the benefit of others—is invaluable to me as a future retiree.

Your perceptive comments inspired me, and I want them to inspire others. Here’s a look at some of your lessons learned:

1. Beware of taxes

If you have to pay a lot of taxes in retirement, you must’ve saved well (a keen observation from Jane K.). But that doesn’t mean you shouldn’t be shrewd about lessening your tax burden (or even avoiding a portion of the burden altogether).

Consider the impact of required minimum distributions (RMDs) on your taxes.

  • Our RMD raised our tax bracket and (considerably) increased our Medicare premium each month. It has been an expensive lesson. –Jerry R.
  • In two years I will begin RMDs, which will show up as taxable income each year, bumping up our tax rate and making us look a lot richer than we really are. –Mike N.

Avoid RMDs by owning Roth assets. (And, if possible, don’t convert all of your traditional assets at the same time.)

  • My wife and I didn’t convert to a Roth, so now that we’re retired, we pay a huge amount in federal income taxes. -Joseph M.
  • Roll over your 401(k) to a Vanguard IRA®, then convert to a Roth. I think it’s best to do the conversion over a number of years to keep your taxes manageable. -Kathy S.
  • I wish that I would have started converting some of my 401(k) into Roth IRAs on an annual basis beginning when I retired at age 57 (and when I was in a lower tax bracket than I am now as a result of taking RMDs). -Ron E.

Think about being charitably inclined to reduce your taxable income.

  • Since the IRS made the qualified charitable distribution permanent last year, I use this method to help me meet my tithe. It’s tax-free and counts toward my RMD. It also reduces the taxable part of my Social Security. -Phil S.
  • I want to donate the remainder of my IRA fund…I am very excited that I can give to charity for the next few years. -J R.

2. Prepare for the softer side of retirement

The hallmark of retirement may be the absence of regular paychecks, but that may not be the only loss you notice when you stop working. It’s important to prepare for the nonfinancial aspects of retirement too.

Make sure you have a life outside of work.

  • Think A LOT about what to do with your time postretirement. I spent too much time thinking about the money part of it, so that when I finally got there, I was taken aback by not knowing what else I would do. I needed more nonfinancial planning. -Maria K.
  • Don’t just assume you’ll enjoy relaxing after working for many years. Your job was a large part of your identity and you need to have a plan to fill that in with something else! -Rhonda S.
  • I was in a highly visible professional position for many, many years. When it abruptly ended, I was at a loss with what to do. So please plan for the day when you are no longer needed. -Jim B.
  • Here’s what I have learned. There are four important focuses to have a joy-filled retirement: They are physical, mental, spiritual, and financial. -Rick W.
  • In addition to saving and being financially prepared to leave your job, you need to make sure you have something to retire to. -Brandon S.

3. Know where you stand on the debt debate, and plan accordingly

For many, retirement represents a certain degree of freedom—freedom from work, freedom from debt, and freedom to enjoy the fruits of your labor. But for others, being debt-free is a misappropriation of assets that could be otherwise invested.

Pay debt off before you retire…

  • I can’t imagine retirement with debt, and it’s the reason I worked so hard to avoid it. -Robert B.
  • At 77, I am still working to try and pay off a mortgage. Don’t let it happen to you. -Lloyd M.
  • If you refinance your mortgage, don’t take money out or extend the time frame—just reduce the overall interest expense. I’m recently retired and still have a few debts. I’m working through them, but ideally, they would all have been paid off by now. -Craig M.
  • I still talk to people who are in their 60s who believe they are saving money by carrying a mortgage! I was mortgage-free at 40, and now I’m 62 and retired and sleep great at night with NO debt! -Blair S.

…or don’t.

  • I am so happy I chose to invest extra cash…rather than paying off my mortgage. My funds have done MUCH better. -Bob M.
  • Monthly bills are a drag in retirement, but if your mortgage rate is lower than your investment return, consider keeping your money out of the house, keeping the tax deduction, and avoiding [the need for] a home equity loan in an emergency. -Jim M.

4. Delay Social Security—it’s worth it

When it comes to claiming Social Security benefits, time really is money. In fact, some of you “bought” yourself some time by drawing down from your retirement savings to pay for daily living expenses.

Your start date can impact your bottom line.

  • It’s hard for investment returns to beat the 8% per-year increase in [tax-efficient] benefits that results from delaying payments. -David H.
  • My do-over would be to delay Social Security until age 70. That would have resulted in several benefits: a larger Social Security payment, lower RMDs at 70 ½, and a larger Social Security payment upon my death for my spouse. -Jim V.
  • I made the mistake of taking my Social Security at age 62, not realizing how much more I would get every month if I waited until I was [at least] 66. Whenever people tell me that they’re retiring, I urge them to find out the intricacies of Social Security benefits before deciding when to take them! -Judith A.
  • What I SHOULD have done was to draw down my 401(k) in lieu of Social Security. Taxes on the Social Security income at age 70 would have been [applied on up to] 85% of the benefit, while now my RMDs are taxed [as ordinary income]. -Erich H.

5. Prepare for the unexpected

Life happens while you’re making plans, and retirement is no exception.

Make good choices—financially and otherwise.

  • I would have reined in my spending and increased my savings while I was married and we were a high-earning couple. After divorce and a job loss, I realized with much regret that good earnings may not continue long-term. -Lori D.
  • Staying healthy and making smart personal choices is critical, as any adverse event can easily wipe out all of your savings. -Adam N.
  • Issues that come up in retirement: parents who run out of health and money and adult children who have life-changing events and need financial help. These can seriously deplete your own savings, so save way more than you think you will need. It’s easy to say, “Just don’t help family members out,” but that is not realistic. -Books R.

6. Think long-term (and help younger investors do the same)

Vanguard’s mantra is to think long-term, and it seems like you share our passion for keeping the future at the forefront.

Knowledge is power. Pass it on.

  • Make sure you leave the next generation better off than you, and arm them with knowledge. -Karl H.
  • Find a good mentor to help you—an actual person whom you trust. Be patient and stick with the plan. There are no shortcuts to wisdom. -Greg N.
  • My father was my savings mentor. He taught me everything I know about saving. I’m trying to pass his knowledge on to my boys. -Gary S.

Advice to younger savers: Keep your eye on the (long-term) prize.

  • Live below your means. Who cares what your friends have? You don’t know how they sleep at night. -Paula M.
  • My wealthy uncle told me three wise words about investing: “Do it now.” Waiting is deadly. -Harlan G.
  • There is so much that’s out of our control (housing appreciation, market returns, etc.). But our savings rate and where/how we invest our earnings is entirely within our control! -Katrina B.
  • You can do it. Don’t forget to help others along the way. No one will care about your money more than you. -Alan W.

Don’t dwell on your “coulda, shoulda, wouldas.”

  • Life is too short to cry over lost money; just learn from your mistakes and move on. -Anonymous
  • Don’t dwell on mistakes. Fix it and get on with your plan. -Paula M.

Achieve retirement success

There’s no secret to retirement success. A successful retirement is the culmination of a lifetime of making goal-based decisions, being cost-conscious, and maintaining discipline. But after reading your comments, I think you already knew that!

Here are some of the investment books you recommend:

  • The Elements of Investing: Easy Lessons for Every Investor by Burton G. Malkiel and Charles D. Ellis
  • The Intelligent Investor: The Definitive Book on Value Investing by Benjamin Graham
  • The Millionaire Next Door: The Surprising Secrets of America’s Wealthy by Thomas J. Stanley and William D. Danko
  • A Random Walk down Wall Street: The Time-Tested Strategy for Successful Investing by Burton G. Malkiel
  • Bogle On Mutual Funds: New Perspectives for the Intelligent Investor by John C. Bogle
  • The Intelligent Asset Allocator: How to Build Your Portfolio to Maximize Returns and Minimize Risk by William J. Bernstein


All investing is subject to risk, including the possible loss of the money you invest.

The amount you convert to a Roth IRA isn’t subject to the 10% penalty that’s charged on traditional IRA withdrawals taken before you reach age 59½.

There are important factors to consider when rolling over assets to an IRA. These factors include, but are not limited to, investment options in each type of account, fees and expenses, available services, potential withdrawal penalties, protection from creditors and legal judgments, required minimum distributions, and tax consequences of rolling over employer stock to an IRA.

You may wish to consult a tax advisor about your situation.