Finding Fulfillment — What Will You Be When You Retire?

Two days ago, my phone buzzed with a trending post on Reddit. The post detailed someone who had achieved FIRE (financial independence and retire early), but says he is ready to go back to work. “The past year has been horrible for me,” he writes, “The lack of socialization, need to get out of the house, and even impulsive urges such as drinking at home has taken their toll on me.” I scrolled through the responses that can be summarized in a few points:

  • No matter what age you retire, you will have to face the challenge of getting social interaction outside of work.
  • If you get your identity from work you will have to cultivate a new identity in retirement.
  • When you retire, you are getting back 8 (or more) hours every day that you now need to fill. Do you have a plan to fill them?

The top response resonated with me:

“It seems like you built your financial independence but didn’t build a personal independence. You are essentially dependent on your work to feel fulfilled, to have a social life.”  -u/cookieraid

I asked Mr. Mechanic what he thought, and he replied that depending on work to feel fulfilled is his “biggest barrier to FIRE,” which piqued my interest.

Although I have been interested in financial independence for the last few years, Mr. Mechanic is on a drastically different timeline than me. Mr. Mechanic is currently studying to be Dr. Mechanic. He still has to finish medical school, then an internship year, then residency before he becomes a fully-fledged doctor, which is an insane investment not just in terms of money but also in time. He will be getting out of school and starting to work around the same time I plan to be able to retire.

Why Retire Early?

The Journal of Business Ethics proposes that while society values being ‘money-rich and time-poor,’ ultimately happiness stems from just the opposite. There is a cap on how much wealth will make you happy, so time affluence is the key to having a happier, more productive society.


The article quotes de Graaf (2003), which states that time poverty can “impinge on people’s happiness by lowering physical health, civic engagement, and family involvement.” Similarly, Kasser and Brown (2003) reported that work hours were negatively correlated with life satisfaction. So what happens when you become financially independent and consider retiring early? That will be great, right? What are the chances we will end up like the man on a forum complaining that early retirement is horrible?

How to Feel Fulfilled

In his book Drive: The Surprising Truth about What Motivates Us (affiliate link), Daniel Pink identifies the three core components to motivation: Autonomy, or the ability to be self-driven; Mastery, or the desire to continually improve; and Purpose, the idea that what we produce is transcendent or serves something meaningful beyond ourselves. If these elements are fulfilled by your job now, that is marvelous. However, if your value is constantly dependent on performance reviews it distracts from the authentic you– an individuality that is built on interests, social ties, and self-sufficiency.

arms-blonde-blur-761977We cannot always count on our jobs to be there for us. Hopefully Mr. Mechanic will find fulfilling work as a doctor, but not everyone will find a job they will enjoy every day for the next forty years. I hope financial independence will let us shape our life so Mr. Mechanic can work for a less lucrative but more meaningful program, and I can work on whatever motivates me. While it is an enviable that you may love what you do, it is a risk to assume that that will always be the case. In the journey to financial independence, it is crucial (as the top commenter pointed out) that we also develop personal independence, detaching our self-worth from our jobs.


Autonomy means taking the reins of our own life. We get out of bed for ourselves rather than for our alarm clanging that it is time to head to the office. Take on a project where you can call the shots. Whatever project you take on, let it be because you find it exciting and interesting.


It doesn’t matter if you are terrible at a skill at first. Pick up woodworking. Start knitting a sweater for next winter. Schedule time in the day to pick up the guitar and record yourself once a week. Over time you will see yourself improve. I hated golf the first 5 years I played, but when I started getting good the game completely changed for me. It does not surprise me that many people pick up golf in retirement. It is something you can keep practicing over and over and slowly see the number on the scorecard decrease. There is definitely satisfaction in slow mastery.


Do you have a mission? In my first internship I helped identify problems with hospital equipment; my work directly helped hospitals around the country draw blood more effectively for donations. My second job was much less rewarding; I helped write software so that dealerships could sell cars. Can you guess which job I preferred? Now I try to find work that I find engaging outside of work, whether that means volunteering or speaking at local events for Women Who Code and more locally, Chicktech. I also write this blog in my spare time which has its own purpose: I want to help others realize that there are other options than working 9 to 5 for life, and I want to help others take mastery of their money.

Identity and Work


In every stage of our lives we define ourselves by the work that we do. However, if we look to our work for fulfillment, we will find that our worth is tied up in performance, net worth, and how many times we answer, “How are you?” with “Busy!”

The Journal of Consumer Research says that the focus on money-rich and time-poor is “driven by the perceptions that a busy person possesses desired human capital characteristics (competence, ambition) and is scarce and in demand on the job market.” We chirrup that we are busy because it makes us feel accomplished and wanted. We know internally that being busy does not actually increase our happiness, yet we still cling to it because it proves our perceived value to society.

Do you ever feel uncomfortable in public just doing nothing? We tend to reach for our phones to text, read the news, or pull up a new podcast instead.

While empirical research suggests that having more time promotes well-being, the patterns we develop during our working life significantly impact how we shape our retirement. Many people find that without work they are left with a void of self, an abyss of time. Free time is tinged with guilt, as if taking time for your life puts productivity on pause. How can we find fulfillment outside of our job, so that we develop an identity that is not conditional on our employment?

The Solution

One thing we can do is recognize that we have been conditioned to value busyness and wealth accumulation this way. “Research on happiness shows that the desire to earn more income is driven by a belief that it will allow for less work and more leisure time,” (Kahneman et al. 2006). We work harder in order to eventually work less, but find ourselves in an uphill battle because the focus is not on fulfillment. Most people earn more income and end up spending it on things rather than time. Craft your own answers to the introductory questions meant to understand more about who you are. Here are what I want mine to be when I retire:

What do you want to be when you grow up?   Time-rich.

What are you majoring in? Whichever book is on my bedside table.

What do you do?  Today I went road biking, worked on the melody of a new song, and wrote 10 pages for a book I’m in the middle of writing.


Joe Robinson, author of Don’t Miss Your Life (affiliate link), writes, “we are more authentic when we’re at leisure than when we’re on the job. We’re doing what we want, when we want, and we’re motivated, not by the usual external payoffs that make us batty, but by internal goals — fun, learning, challenge, joy, the experience itself […]” Essentially, you are not what you do.

If you were to stop working right now, do you have projects, whether through volunteering, after-work activities, or side-hustles that would satisfy your internal drive? What do you find fun, challenging, and engaging? Please share in the comments below!

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  1. Great post! It’s hard to believe that someone can pursue financial independence, reach it, and not have a plan for what they want to do when they get there. Makes me wonder why the person ever pursued it in the first place. I think that shows the importance of looking for meaning rather than financial freedom. I listened to a podcast episode a while ago about a guy that started a recycling company that only hires people who have disabilities or mental handicaps. I doubt he’s ever going to retire because his “job” gives him such purpose.

    It seems like you usually end up making a lot of money even after your retire if you start doing the things that truly give you a sense of meaning. I’m pretty sure Mr. Money Mustache makes more money from his blog than he ever did during his career and he barely even tried to monetize it.

    1. Thank you! I agree that it makes you think about the motivations of pursuing financial independence. I have about ~10 years to go before FI so I have some time to ponder what I want that to look like, whether I continue to work or choose to do something else. Yet it’s never too early to think about what gives you meaning in or out of work. It definitely is pretty inspiring to see the portfolios of early retirees continue growing even though they planned to have extra buffer room while they just do what they love! It

  2. I like the sentence about the caution of a “void of self, an abyss of time”! I think that the beauty of financial independence is that you can try earning some cash by making things to sell on Etsy or trying some other entrepreneurial endeavor without the stress of having to make a corporate deadline or to make enough money to pay the bills. Mark Cuban on the Shark Tank episode I watched tonight said, ” “I’d rather work 80 hours a week for myself making $50,000 a year than work for someone else making $100,000 a year.” Why? Because it doesn’t seem like work.
    I build camper trailers as a side hustle (check out my blog). The work is incredibly fulfilling,and empowering. It gets me outdoors, provides exercise, improves my mental health because the concentration empties my thoughts like meditation does. And then I can sell the the campers for 3-5 x the cost of materials! The next step would be to build something larger like a ‘tiny house’! Doesn’t that sound fun?
    Stepping away from a regular job though is rather terrifying. I think a solution to this would be a “sabbatical” where one dips a toe into the water by taking an adult gap year or even a break for a couple of months. Maybe like like the guy you write about I would find out that the leisure life is not for me.For now, I am content at my 9 to 5 so I can afford to take my time.
    “Dreaming big” is overrated in my opinion. Contentment is where it’s at. I think financial independence can take you there.

    1. I’ve heard of the “sabbatical” solution to be: retire early, retire often. Sometimes a break can be enough for you to identify what you really want to be doing. It’s great that you are content in your 9 to 5 AND have a side hustle that is fulfilling and empowering!

  3. Hi FM, So many thought provoking ideas in this post! Brilliant! I didn’t come into early retirement with a lot of planning (but that’s kind of my personality). What really did help though was that I never saw my being a teacher as my identity. I had a lot of complicated feelings about my job. That being said, I’m definitely glad I quit full time, though I have moments of sadness that I left the profession. It’s been over a year since I retired, and I’m still trying to figure out what my retirement will be all about. I’ve done a lot of cool things, but I can definitely add more activities to my daily schedule.

    1. Thank you so much! It is really interesting to get another perspective from someone who has retired. I’m sure many feel very mixed feelings about leaving their profession. Would you be interested in picking up teacher-like hobbies? After school program volunteering, tutoring, or something like that? Or are you happy to not be teaching at all? What’s cool is you have plenty of time to figure out what your retirement will be all about 🙂

      1. I did part time work for a few months after I retired, teaching adults English. Since I never taught adults, I had to do a lot of extra planning so it became like a full time job and I had to quit, ha! But I don’t regret the part time work because I got to meet a lot of new people and learn interesting things about diff countries. I’m not sure if I’ll return to teaching in the traditional sense. I am trying to start a support group for creating healthy habits for cancer survivors and caregivers, which I’m hoping to launch in 2019. Thanks for your encouragement to make my time!

  4. I actually work more like 6ish hours a day, so fewer to fill 😉 plus I volunteer in the evenings, so I fill up more time. I don’t plan on quitting anytime in the near future, but I’m a serial time-filler, so that lack of ability to fill my time with meaningful endeavors is not on my list of concerns for eventual retirement 🙂

    1. Sounds like you are already setting out those patterns for time-filling and getting meaningful work early on! Rock on 🙂 I used to fill every second of every day but have since rebelled and don’t do much extra stuff in my spare time. Volunteering in the evenings sounds like a great way to do it, what do you volunteer for?

  5. Excellent article! I think this happens more often than people realize. My Dad had this happen to him. He retired early (long before FIRE was talked about). He has plenty of leisure hobbies to pursue however, he lost significant connection with the local community and general life purpose. He was so focused on escaping his career he failed to consider how his career fulfilled some of his basic life needs. He now works PT as a tutor for a local community college and is much more satisfied with life.

    1. It’s great to hear that he found something that gives him purpose. It seems like retiring early is very much a “grass is greener” type situation, and many people don’t realize that even in retirement you still need to do something to feel fulfilled. Thanks for sharing his story!

  6. The idea of the article and it’s value is dead on. However, I frown at the conceit of those comments that are judging those that earned their financial freedom and did not ‘have a plan’ for their Personal Freedom immediately following. Obviously, first gain your financial freedom to get any credit and then you can speak to how to find happiness and enlightenment after you have swam upstream for a few years. Any plan you have beforehand, you can throw out the window after year 2. The first year we all had the hobby targets like golf and guitar. Guess what…if you were not interested enough in these hobbies to find time before, you just we’re not that interested. Volunteering, yes it is fulfilling, but it is also work and once again if it was really your personal mission to do XYZ, you would have done it before as well. My point is that you can make your life after plan, it will not work as planned, and you should not judge. FYI – I am much happier with financial freedom and time freedom, have achieved something great I could not have without it, but it is not the Valhalla you may think.

    1. Good point, and interesting to hear from someone who has already achieved financial freedom. Hopefully this doesn’t come off as judging those already in retirement; everyone makes their own way and it’s not easy!

      Just like how we don’t always assume careers we might have imagined while we were in University, retirement will not always look like what we expect. I think your point speaks to one I made as well: “the patterns we develop during our working life significantly impact how we shape our retirement.” All those ‘hobby targets’ and volunteering should be something you do while working if you also expect to do them in retirement. And you make a good point about planning and how that goes out the window. How did your plans change when you actually found financial/time freedom?

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