Ask Nick: Am I Ready To Retire Emotionally?

Hi Nick,

I’m 60 years old. I know I have enough to retire, but for whatever reason, it feels really hard to pull the trigger. If the money isn’t the problem, what is? Is this normal?

This question is so good. It’s one that I think is in the minds of way more people than those who actually say it out loud. So kudos for being up front about it.

I don’t know the psychological term for this, but there’s something that gives us pause when a far-off goal finally becomes imminent. Regardless of where you are in relation to your retirement, you’ve probably felt a version of this at some point in your life. Maybe it was when you moved out of your parent’s house to start life on your own in college, or the night before your wedding after spending much of your adult life single. In those kinds of transitions, there is a similar feeling of a new normal. There’s this general sense of:

There was the life I lived before, and now it’s going to be slightly different. Not bad. Just different.

Retirement is similar in many regards. Even if you’re excited about the transition, your current lifestyle is the one you know and are intimately familiar with. Retirement becomes the step into the unknown. Jumping this chasm feels like leaving a warm bed on a cold morning.

Yes, life is more interesting when you’re out and about in the world, but “current me” is comfortable. And I like comfortable.

Retirement adds one more wrinkle that, while maybe present in the other transitions, takes center stage here: identity, or more specifically, the need to reset it. Once retirement becomes a near-term reality (rather than this abstract goal far off in the distance) people begin to more fully appreciate how much they've tied their identity, self-worth, and life routine around work.

I have an experiment for you. The next time you attend a networking event, a wedding, or some other event where you mingle with people you don't already know, I want you to avoid discussing your work or asking about someone else’s work. It's really hard.

At least from the perspective of us here in the United States, our career or profession is almost synonymous with identity. It's the first thing you use as a proxy to determine all sorts of things about other people, from their personality to their socioeconomic level to a general sense of “could we be friends.”

And when we say the quiet part out loud, we all know it’s stupid. I’ve met warm, personable engineers, introverted salesmen and women, teachers who are quiet millionaires next door, and investment bankers without a dollar in savings. But even if we know this, it doesn’t change our initial reactions, nor does it right-size the prominence of work in our culture.

We might occasionally pause from work to watch a reel on Instagram that reminds us that you should work to live rather than live to work. We nod in agreement. And then we get back to burning that midnight oil.

So yes, at the end of the day we associate too much of who we are with our work. But it also makes sense, mostly due to how much of our waking lives we spend doing it.

We’re talking 8-10 hours per day for the middle 30-40 years of your life. That’s not even considering your commute. Add in kids, meals, household chores, and the obligatory hour or two watching Netflix or doomscrolling social media, and that’s a full day. The weekend is spent catching up on stuff you didn’t get to during the week, and because there’s rarely room for much else, work quietly becomes who you are.

It hurts worse for successful professionals who are in the peak of their careers, because expectations increase with your income and your title, so you've actually probably never been as tied to work as you are right as you start thinking about stepping away.

All of which is to say that stepping away into retirement can become terrifying because 90% of your identity is about to drop into nothingness. A void.

If you listen closely, you can hear newly retired folks acknowledge this void. It usually happens when a new retiree meets someone new, and when asked the aforementioned “what do you do?”, they say something like:

I used to be a ________________.

Ouch. That's terrible.

While I think people often build retirement into something bigger than it really is, it definitely should not be this place of boredom where you daydream about your former life, especially when that former life was a place you were dying to get out of!

So Step 1 to being ready to retire is figuring out how you want to fill that void. And I want to be brutally honest here. Filling that void can be difficult. Really difficult.

As we just mentioned, it’s not like you currently have a ton of free time, and we’re going to have to do some brainstorming on how you’d like to spend your time to maximize your goal, whether it’s happiness, purpose, or some other metric.

That said, not knowing what you’re going to do is not permission to continue delaying and deferring retirement because you're scared of what's next. It's just a realization that you need to dedicate some time to plan for what you want the rest of your life to look like, and then take that first step.

If you’re able to pull the trigger before reaching this conclusion, some retirees spend their first few months answering these questions. If you feel like you need to know this answer first, then considering options like sabbaticals or “mini-retirements” can help create the time and space to answer these questions.

So to answer the original question, I think you feel “ready” when you're more excited about what you're going to do with your life post-work than you are worried about what you're leaving behind. It sounds like it may take some work to get there, but rest assured, you will get there.

Over the next few weeks, I’ll write more about what this first step looks like. I hope to see you there.