Unhappy in early retirement? 7 things to try before you even think of going back to work.

Leaving the workforce grind behind for the autonomy and effortless life of retirement—early or otherwise—is something most would say they look forward to… until the day finally comes. While many of us can’t wait to shed our corporate identities and make that final walk out through the lobbies of our office buildings (with some folks holding their middle fingers in the air), this major life change can also bring a rush of questions and concerns.

It’s totally normal to feel a bit lost and unsure of how to manage and prioritize your time following this type of life-altering move.

After quitting your job, waking up that first morning when you’d normally be at work can be a bit unnerving.

“Boy did it hit me,” Brandon of Madfientist said about his first day as an early retiree. “You would have expected it to be the best morning ever but it was actually the only time in the entire first year that I freaked out about the whole thing. I had escaped the normal life script but now I was in uncharted territory. I was staring into the vast unknown and the immense gravity of the situation freaked me out (much more than I expected),” he said.

“Have you ever planned a really big trip? Maybe it was your honeymoon or a trip to a place very far away that you had to dedicate a lot of time to plan out. Even though you spent months booking flights, researching hotels, and telling all your friends about your upcoming trip, the reality of what you were doing didn’t actually hit you until you got off the plane,” Brandon said about that day back in 2016.

Taking extra steps to prepare for the transition may ease anxiety for some, although like many things in life (marriage and parenthood come to mind) no amount of planing will fully prepare you. They simply require first-hand experience.

However, when you create  a plan for the beginning of your early retirement, you can reduce this anxiety. After all, you wouldn’t be in this Champagne-problem-predicament if you weren’t a planner. You put a lot of thought into your financial steps to early retirement, so applying those skills to your vision for your new life only makes sense.

7 Retirement tips for millennials and other early retirees

There are many tips of advice for boomers looking to figure out what to do as retirement nears but those tips aren’t always relevant for Gen X-ers, millenials and younger retirees. That’s why TSR has pulled together advice for people interested in FIRE (and who were born after 1960):

1. Prevent the little details of your present from putting a damper on your future.

You’ve probably thought about some of the things you’ll be doing post 9-to-5 that will bring you joy in your retirement. Artistic pursuits, travel, volunteering, family. But have you remembered to think through some of the less exciting details and/or issues that might come up?

A post on New Retirement provides prompts such as “who do you see regularly” and “what could go wrong later in life that’s possibly preventable.”

New Retirement also notes the importance of thinking about how your daily habits are going to impact your future health and what it might mean for your aging process, your financial requirements and your living arrangement. The results of thinking through these types of details can be very powerful and may lead some to change their habits.

For the couples out there (yes, you DINKs reading this), there’s the topic no one really talks about until or unless a marriage falls apart: divorce. It’s not that uncommon. Yet few of us consider the ways in which a divorce might impact our finances. And if you’re a married couple living on your retirement savings, it could be devastating to your lifestyle.

The subject may be uncomfortable to discuss but that doesn’t mean we shouldn’t contemplate the possibility and the toll it could take on our financial solvency. Nine states take a community property approach, where assets typically are divided in half. This includes joint retirement accounts. Other states follow an “equitable distribution” doctrine where each person’s earning ability, personal assets and other facts are taken into consideration. Regardless, without a prenuptial agreement, divorce is more likely to have a dramatic impact on one’s financial picture.  

Don’t mistake this as a suggestion to ruminate on the scary “what if’s” that only serve to paralyze thinking on the viability of FIRE. Rather, the point here is to explore whether to take action sooner than later to help ensure a smooth retirement. Read arguments against some of the scary ”what if’s” in a blog Steve Adcock did a few years ago.

2. Envision and set a daily or weekly routine.

That’s right--I said “daily” and “routine.” Because it’s pretty unanimous that routine increases happiness, especially when it’s one that you have control over.

As FIRE blogger Darrow Kirkpatrick put it, “research and writing is the backbone of my new weekly routine. I still keep a fairly standard work schedule, but it’s by choice now, and that feels totally different!”

Those who have left the workforce at all ages acknowledge that settling into a routine and order brings a measure of happiness.

Kirkpatrick admitted the change took some adjusting. “The reality of early retirement has surprised me a bit. Of course, I never bought into the stereotypes: morning on the golf links, afternoon at the beach, evening in the hot tub. But I did expect to have more space in my life after I retired. Actually, I got busier.”

Some of that routine might feel a bit like when you went to your job. “Blogging lets me produce something creative that’s valued by others—a product that I’m proud of every single day. Perhaps most importantly, it’s plugged me into a network of savvy, interesting people who are making a difference in the world,” Kirkpatrick said.

3. Learn to say “no.”

From the vantage point of full employment, looking at the retired life and assuming it will be overflowing with time for all our heart’s desires is easy. This, however, could not be further from the truth.

That perception of endless amounts of time available to those without full-time employment sets the stage for the pitfall of saying “yes” to too many requests. Brandon of Madfientist explained, “My problem with my first year after leaving my job was that I just said ‘yes’ to a lot of commitments... I was like, why not because I have the time. But by the end of the year, I realized I didn’t make any progress on the projects that are really important to me.”

And keep saying “no.” In his second year, he started saying “no” to a lot of requests and “yes” to opportunities that sounded like fun. That still didn’t feel balanced. Brandon reported he still felt short on time to do what was important to him. By the third year of retirement, Brandon reported feeling more balanced with his time.

“So this third year was marked by saying no to most things … it’s actually turned out to be great because I have made a lot of progress on the things that are really important to me. And that definitely gives me more lasting deep happiness than simply you know, just having another fun trip or something,” he said.

In that third year, Brandon said he recognized just how powerful inertia is. “I’ve realized over the past year, how important it is to always ask why you’re doing something and whether you still want to do it. Because it’s really easy to just keep doing the same thing, and not really do the things that you want to do.”

Amen to that!

4. Keep tabs on your financial picture and touch base with a pro.

Often in early retirement, you’re relying on your money to make you money. So, of course, it’s important to keep an eye on market performance, and how your finances are impacted, but also to be cognizant of any tax or other regulatory changes that apply to you and your portfolio. You may want a financial advisor or a financial planner has the skills to best support you.

Investopedia suggests gathering information on all of your retirement accounts. Anyone who’s worked more than one job most likely has multiple employer-granted investment accounts. This is of course is in addition to Social Security benefits. For anyone who’s one-half of a couple, the number of accounts to track doubles, as does the importance of keeping close tabs on your finances.

5. You don’t have to stop hustling!

If you’re feeling a bit anxious at the precipice of quitting the work-a-day world, it might have to do with a mentality that once you leave your job, there’s no going back. “Early retirement” isn’t the same thing as “never make a dollar in your life ever again.”

Retirees--young and later age alike--blog about their money-making endeavors. The obvious option for people with skills conducive to consulting and independent contracting is to do what offers the best pay.

Sometimes though, we elect a side hustle for the fun it brings over the pay. While driving for Lyft might not be the highest-paying opportunity, financially independent people do it simply because they enjoy meeting people and driving. It can be a hobby that has at least a trickle of a profit.

Task Rabbit is another great option for making extra money on your own time. If you have a trick for getting a tub to sparkle, why not make extra money helping a new homeowner impress their houseguests? (Also, please contact our writer, Melissa, she’d like to learn how to do this without needing a chiropractor adjustment after…)

6. Know that “purpose” rules.

Regardless of why you want to retire early and how you’ll spend your time, having a clear purpose helps guide your priorities, how you spend your time and how you spend your money. Purpose is essential for happiness, regardless of your financial or work status.

Fortunately, you can find purpose.  According to a 2010 study published in Applied Psychology, individuals with high levels of eudemonic well-being—which involves having a sense of purpose along with a sense of control and feeling like what you do is worthwhile—tend to live longer. Researchers found that the people with the strongest well-being were 30 percent less likely to die throughout eight-and-a-half-years following the study.

“There’s no way in hell the absence of a full-time job will ever truly cure you of your lack of purpose. It won’t happen. If you quit your job without something else in your life to keep you busy with a genuine sense of accomplishment, you WILL go back to work or you’ll feel dreadfully hollow in early retirement,” FIRE blogger Steve Adcock said in a 2018 post.

For some, finding a second calling fills a void. “I found that whatever I tried — volunteering, travel, taking courses of interest — didn’t fill up my need for intellectual stimulation and engagement with others,” said Allyn Keiser, in a story about retiree regret by the Washington Post.

“I’m in my mid-seventies and working as a consultant helping executives become more effective at work. I’ve only been doing this for the last dozen years, but I feel like everything I’ve done previously has prepared me for this. I see it as a calling, and I’d like to keep at it as long as I’m able.”

Keiser notes that he still leads a life with the hallmarks of a retiree, such as volunteering and traveling, but prefers to also have fulfillment from his consulting.

7. You can always go back—this time, on your own terms.

The great thing about FIRE is there’s no real downside. So you ditch your job and you give early retirement a go. What could go wrong? Most people who do it have a lot of energy and are creative, which is how many soon find themselves in pursuits that also generate income. And, if you change your mind, it probably wouldn’t be tough to rejoin the workforce. Especially considering forecasts for growth in jobs that coincides with a shortage of workers for the foreseeable future.

Attitude always wins—lean into your optimism

We all know this, right? Steve notes anyone looking to retire early and enjoy a life outside the workaday paradigm must be “pretty damn optimistic about the future. The thought that your stash will last you 30, 40 or even 50 years or more without having to work means you’re generally positive about the future and believe that things will work out.”

“Early retirees take a glass half full approach to most things, from making life-altering decisions about work to picking the right wine to sip on during dinner – and everything in-between.”

Even though staying on the sunnyside takes work, it is well worth the effort.

Pretty soon, you’ll find peace, get in a groove and get down to what really matters. Most likely, you’ll take to early retirement like a fish takes to water.