Advice to My 23-Year-Old Self

One of my favorite things about blogging is the connections we’ve made with our readers – whether in person as we travel (over a dozen meet-ups last year!) or over the internet.

This e-mail from a reader caught my attention last week:


I hope you and Daniel are doing well and enjoying semi-retirement! I’m hoping you could share some advice that you’d give to your 23 year old self.

I got my bachelors last year in Marketing and have worked for a cool, highly successful company in a southern U.S. city since, salary about $40k pretax. But here’s the thing, Matt, you’ve ruined me.

Since I discovered semi-retirement was possible at a young age, I’ve become obsessed with the concept. I’m a rock climber, mountain biker, etc., so the thought of being able to pursue those hobbies full time while my body is at peak health is incredibly enticing.

I’m not sick of working, as a concept, though I am so sick of marketing. I am more like you than the rest of the FI community in that I have no problem working again someday; in fact I know I want to. If I could find a way to semi-retire for a few years, I could use that time to pursue my age-restricted hobbies and develop skills for re-entering the workforce.

So, what would you tell yourself at 23 to make early retirement planning less painful, more productive/efficient, or what have you? And any advice for my specific situation?


My response quickly turned into a multi-page letter, and I decided to post it here.

Here are five pieces of financial advice I’d share with myself at age 23.

Advice to My 23-Year-Old Self - The Resume Gap

1. Prioritize people.

The very first thing that comes to mind when I think about that period of my life is the people I shared it with. Your early 20s are the time to strengthen and solidify your best friendships. Daniel and I saw a ton of good friends on our recent road trips around the U.S., and most of them are people we got to know well at that time in our lives.

People start getting boring when they turn 30! Relationships, careers, and kids start taking precedence. Say yes to every opportunity to build relationships now, and they’ll stay with you for life. Yes, these opportunities sometimes come with a financial cost – like a weekend trip or a night out with friends. Sometimes, though, they might actually save you money – like living with friends instead of renting your own apartment.

Same thing goes for family. I’m pretty close with my parents, and I notice their age now more than ever. Never put money or work ahead of the people in your life.

2. Make your work life the best it can be today.

My strongest reaction to your e-mail was your point about being sick of your field. Marketing was my college major, so I can relate. I’ll always remember the moment I decided against it as a career path. My professor was describing how he spent years of his career as the brand manager for the “Helper” franchise – as in Chicken, Tuna, and Hamburger Helper. Everywhere he traveled, he would duck into grocery stores to check on the shelf placement and display of the products. One of his biggest projects was consumer-testing and piloting a new product, Lobster Helper, which ultimately flopped. “Oh, fuck,” I remember thinking to myself in class, “There is no way I can waste my life doing that.”

This is not the look of career fulfillment

This is not the look of career fulfillment

Anyway, enough about the Betty Crocker line of packaged foods. Here’s my point: Work occupies more of our time than anything else in our lives. If your day-to-day work life isn’t happy, make changes immediately.

You live in the land of opportunity, have a college degree, and are capable of writing a coherent e-mail. I guarantee there’s work out there that you’d love, and it probably pays at least $40k a year. I’m not delusional enough to think that you’ll find a job that’s great every single day, but don’t get stuck in a rut. Work that you enjoy might make the difference between a relaxed path to early retirement and a really unhappy one, even if the timeline is longer. You can’t live for the future alone.

3. Figure out how long you’re willing to wait.

I’m kind of a wishy-washy blogger, Buster. I write shit like “Don’t wait,” but then I also say that you can’t “just go” without planning and preparing. Ultimately, you’ll have to figure out the timing that will work for you.

You might decide that rock climbing and mountain biking are essential to your life right now, and you’ll do anything to make it work — even if that means taking odd jobs, living in a van, and eating rice and beans for every meal.

Alternatively, you might be willing to wait a decade or more to pursue those things full-time. You wouldn’t get to enjoy your youth in quite the same way, but there are advantages to this path. Our friends over at Our Next Life, for example, are retiring in their late thirties with enough financial security to never work again. You might value the peace of mind that comes with that approach. Spending years focused on your career also lets you build skills and experience in a way that’s hard to replicate with shorter career stints.

The answer for me was somewhere in between. I managed to reach FI in my twenties, but I was due for a major career change or time away from work regardless of whether I’d hit my “number.” Taking time off had been part of my plans since my first day in an office.

Another thing I’d remind myself at age 23: 30 years old is not old. (Sounds like something a 30-year-old would say, huh?) Neither is 40. I don’t feel much different from how I did at 23. I still plan to pursue a lot of physical hobbies in the coming decades. If anything, I might be getting more out of this semi-retirement experience now. I’ve had more time to figure out what I value, and having years of career-oriented life for comparison makes every day without a job just a little bit sweeter.

4. Income matters.

If you’re serious about early retirement and you’re already living economically, growing your income will have by far the biggest effect on your savings. Our Next Life, Think Save Retire, Go Curry Cracker… many of my favorite FIRE bloggers who called it quits in their thirties had six-figure incomes. It’s possible to retire making less, but it’s harder.

In good news, I bet you can already afford a sick minivan like ours

You said you’re earning $40k now. If you’re serious about enabling early retirement or semi-retirement in the next decade, do you have a reasonably clear path to making $60k? $100k? If not, I’d consider looking for work with higher earning potential, so long as it’s also compatible with my points above.

Start turning your skills into side income, too. If you want to take time off before you reach financial independence, being able to generate self-employment income could be extremely helpful. Even just $10k a year could probably cover most of your living expenses while camping and climbing, for example.

5. Relax. You don’t need to know the master plan yet.

At 23, I knew that I wanted to take time off from work at some point in my twenties or early thirties. Did I have any notion that I’d be here in Thailand this month? Of course not. Your life circumstances will change over the coming years in ways that are impossible to predict.

As Steve Jobs put it in his 2005 Stanford commencement address, “You can’t connect the dots looking forward; you can only connect them looking backward.” Looking backward, I see that the most valuable thing I did was laying the groundwork for financial independence: working hard, saving money, and optimizing my spending. At 23, building your savings and being committed to taking time off in the future can be your entire plan.

So don’t stress about whether you’re 2% or 12% of the way to your “number,” and don’t feel like you need a concrete goal or deadline. The more skills you build, the more you save, and the more flexible your spending, the better equipped you’ll be to take the leap into something new like semi-retirement when the time feels right.

Readers, anything you would add or change? What would you tell a recent college grad interested in financial independence? I’d love to hear your perspectives in the comments.

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  1. Love that Steve Jobs quote – it’s so true too. I’m 36 now, and looking backwards it’s easy to see how all my decisions over time led to the place where I am now. But at the time, in my 20’s and 30’s, the path forward was not clear. I would worry about the fact that I didn’t have a five year plan, but then I’d talk to people in their 30’s and 40’s and realize that no one ever had a plan. Things happened, opportunities came up, and they ended up where they were.

    • I completely relate to that experience. I grew up thinking for some reason that everyone older than me had it all figured out — and that my parents knew exactly what they were doing. I think you realize with age that everyone is doing this for the first time, and there aren’t many people living their perfect plan!

  2. All good advice! The one thing I would add would be to fit in as much of that stuff you love now. Don’t put it off till you hit FI. One of our dreams was to travel. So when we got an opportunity to move overseas we jumped at it! We were able to travel through 27 countries over the 4 years we lived there. But we also weren’t high earners. So figure out how to do it now or maybe wait 20 years.

    • Good points, Ms. Montana. It’s not just about making your work life the best it can be; I’d work on making *all* of my life the best it can be. That includes taking advantage of as many opportunities as you can to follow your passions part-time, whether it’s travel or climbing or anything else. With the ease of travel-hacking these days for people with access to American credit cards, that’s a great one that doesn’t have to cost much money.

  3. Good advice. Man to be 23 and already thinking about this stuff is FANTASTIC! I started our road to FI in my early 30’s. Its amazing how fast time flies and how quickly FI can be reached by make some changes to your lifestyle.

    • Agreed! Not only does it give you time to take advantage of compound interest, you also get to start before you’ve built years of lifestyle inflation into your routine.

  4. I would add: Your body will function a lot longer than you think. I said something on the Mad Fientist podcast about wanting to retire while we’re still able-bodied enough to do the outdoors stuff we want to do (which I meant in terms of the possibility of inheriting my dad’s disability, and because we know that if we work our high-hours jobs forever, we’ll continue to get unhealthier), but I got whacked down pretty hard by a 60-something who reminded us that plenty of folks in their later years are still in fantastic shape, maybe their best ever. And living in a mountain town reminds me of that all the time, as we regularly get lapped by 70-year-olds. So the urgency to do things at peak physical condition isn’t as grave as a lot of early-20s folks may imagine!

    • Yep, I’m reminded of that every time I’m on the mountain and get passed by someone twice my age! (Admittedly, the ten-year-olds are often kicking my ass, too.) I still think there should be *some* consideration for age — not everyone can be the 80-year-old marathoner or 100-year-old sprinter — but you’re right that it’s not as urgent as a lot of young people make it out to be.

    • ExploreMountainsOnSkiFoot&Bike

      March 28, 2017 at 12:58 pm

      I would echo this. When I was a ski bum, some of my regular ski pals were in their late 60s and early 70s. We skied hard all morning and they weren’t more than 1-2 turns behind me (I was 30 at the time). They would have a cup of soup and beer and then head home, and I would ski the afternoon. They showed up over 100 days each season. I think maintaining physical condition throughout a lifetime is the key and challenge.

      • I think I’d have lost all my toenails and a few limbs if I skied 100 days in a season. Or maybe I just need better-fitting boots or to ski a little more responsibly 😉 I completely agree with you: the people at that age who are in great shape seem to be the types who have maintained it throughout their lives — not the ones who suddenly decided at 55 that they wanted to get in shape. Good motivation to stay active!

        • ExploreMountainsOnSkiFoot&Bike

          March 31, 2017 at 10:50 am

          Great fitting boots go a long way to enjoying skiing and keeping your toe nails. Skiing in control helps to keep from falling and hitting objects, which tends to preserve the limb integrity.

  5. Thanks so much for the advice Matt. I’m 25 and I happen to be getting my bachelors in marketing too so this really spoke to me. I especially liked the part about doing what you enjoy. I used to worry more about choosing a job that would make the most money over a job that would provide happiness. Now that I’m back in school I realize how many people can’t even write a coherent, correctly spelled essay. With your advice I feel more confident that I’m going to be just fine and I’ll connect the dots as I go.

    Being financially smart takes a certain level of care and conscientiousness. Sometimes that same quality makes me overly careful and I always need to have a perfect plan. Not being able to have a clear plan about my future career has been annoying. So it’s nice to read that it’s ok to not have a complete 5 year plan.

    • Good to hear from you, Elsie! It’s helpful to the FI journey to look for high-paying work, of course, but I wouldn’t recommend doing it at the cost of one’s day-to-day happiness. The only exception might be sticking it out for a year or two to reach a financial target — but even then, I could go either way. You’re clearly smart enough that you’ll do well at whatever you choose to pursue. So keep at it!

  6. Hamburger Helper – too funny! I spent many years working in brand management at General Mills, although I never worked on Hamburger Helper myself. It’s a different strokes for different folks thing – I really enjoyed the brands I worked on … Pillsbury, Totino’s, Yoplait, and Progresso … and it was a lucrative career. It sounds like the person looking for advice might have found themselves in the wrong career or wrong company. We all have tough days at the office – if you are doing something you really enjoy – you will skate through those days.

    • Uh oh, sorry if I insulted your past career choices! 😉 That lecture made an impact on me as an impressionable 19- or 20-year-old, though I think now that I could enjoy many jobs with the right work-life balance and a good team and company culture. Your last point is a really good one; if the good days far outnumber the tough ones, that’s probably a recipe for success. If not, time to change course.

  7. Knowing what I know now, I would tell kinda the same as Ms Montana: start to live now. FI does not have to be the end goal. It is a mindset that teaches you to live intentional and to spend time and money on things you like.
    To put it black and white: either you work hard for 10-15 years and be FI from mid 30ies for the rest of your life. Or live life intentional now, and be FI some point in time with fun in between. Being a late starter, I only have option 2 left. We make the best out of it!

    • Definitely, Amber. It’s apparent to me in how few people in the FIRE community are actually completely “retired” and not pursuing any side projects or work. FI is a great enabler of choice, but it’s not the end goal.

  8. Life happens now. I’m a hardcore planner. My parents called me Type Double A because I can be so…precise…let’s say. But we’re really only given today. So I would never ever consider making myself miserable for 5, 10, or 15 years to walk away from it all at 45 (or 40 if you start younger than me). Different strokes for different folks, I suppose.

    Love all of this insight, Matt! So great of you to give such a thoughtful reply to a reader!

    • Yep, the only time I’d recommend sticking it out is if you have a few months or maybe a couple years left and then you can get out. But 5 or more years? No way. This is all we’re given; why sacrifice decades of it to something we don’t enjoy?

  9. I’m 43 and I do have a similar mindset to you about the ‘don’t wait’, but do plan. I’m very much a risk taker and I think it leads to a more fulfilling life. What I would suggest to young people is just go after your dreams. You can do almost anything you want. Don’t wait until things are purpose. Start taking steps now. You may fail 20 times, so don’t wait to start failing. Just go do it. Life is short to be testing the “helper” meals! 🙂

  10. Looking back over the last 15-20 years is like a whirl win for us. I think the master plan piece reads the most true. Had you asked me if I’d be where I am now at 20 I never would have believed you. That being said, “luck favors the prepared”. A step too far back would make someone think I lucked into my current life. Sure I had no idea I’d get here, but each time I was prepared when the path veered to follow it. So I guess I’d add, be flexible. Opportunity can appear where you never expect it.

    • Good points, FTF: we might not be able to see our next hundred steps in life, so continually preparing to take the next one is about as much as we can do. There are so many external factors, too, that we can’t know exactly how things will play out. Best to be flexible and open-minded.

  11. I would tell a 23 yr old to save half their income and develop real life-long hobbies. Also, move to a new place. Your early to mid-twenties is a time to roam!

    • I like the hobbies advice. I have a hard time believing it when I read about people retiring and not knowing what to do with themselves, so they go back to work. I feel like I could occupy myself for decades without a job! And we agree about using this as a time to roam, if that weren’t completely obvious 😉

  12. Excellent points all. I would add:

    Travel if you can. Travel far. Travel till you get a little bit outside your comfort zone. It will expand your mind in ways that you won’t expect.

  13. ExploreMountainsOnSkiFoot&Bike

    March 28, 2017 at 12:55 pm

    Nice recommendations.

    My additional recommendations to Buster include reading Micro Adventures and Grand Adventures by Alistair Humphreys. One can have amazing trips, adventures and time in the mountains in evenings, on weekends and inside two week vacations.

    I have been following the mini-retirement path, though I did not know it had a name nor was I intentional about. After working for four years, I had saved $70k in cash in addition to maxing out 401k and IRA. I traveled and ski bummed for 2 years on the 70k before switching careers and taking another job. Ten years later that 401k and IRA money has be about half way to my FI target.

    Saving $5,500 in an IRA in your early 20s does not seem like a lot when compared to a million of people in their 40s. Compound interest is your best friend when you can save money in your 20s. It will be a lot more than you realize in a decade or two.

    Also, I am a stronger skier now in my mid 30s, than I was in my 20s. Living near the mountains enables me to go for mtn bike rides and ski tours in the evenings and weekends year round which increases my sanity and conditioning.

    • Great points here! I’ll have to add that to my reading list. You can create a lot of adventure in your working life, even if it’s not quite the same as full-time. Also love your experience with “mini retirements,” which are totally achievable for many people. If you’re saving from a young age, that compound interest will work wonders in the background!

    • Buster here, I just have to comment because this is *exactly* what I’ve dreamed about. I’m on a path to 50k in 4 years, with an IRA maxed. After I hit that I want to bum for couple years and come back in a different career, using that “bum” time to (1) play and (2) develop skills to let me re-enter the workforce where I want to.

      So basically your life sounds like the dream to me. Thank you for posting. Just to know someone has done this successfully really raises my risk tolerance.

      • Awesome, happy to see you in the comments! I think that is such a solid plan — and one that I wish were more common. That’s more or less what Daniel is doing tagging along with me on this adventure.

      • ExploreMountainsOnSkiFoot&Bike

        March 31, 2017 at 11:00 am

        Buster, Glad I can be an inspiration.

        I never regretted the money I saved. I rarely remember all the money I spent. Having said that, I do spend money on things I am passionate about (e.g. comfortable backcountry ski boots). I cut expenses, stress, hassle out of things I do not care about (e.g. no yard work and bought bread machine at thrift shop).

        Your plan sounds good to me. Have fun outside.

  14. The fittest people I knew in my early working days (17-21) was a 56 year old man who would routinely run marathons before arriving to work his full shift. Every. Day.

    The fittest people in select outdoors sports I know now are in their 40s-freakin 70s.

    If you’re smart and lucky enough not to get gut-punched by a disease like I was, you have the potential to enjoy a HECK of a lot of good years full of career and outdoors.

    Though, I had to laugh-cry at “get boring in 30s” and “30 isn’t old”. I never felt like 30s was old til I got here. But, really, I was boring at 22, sharing the doctor waiting room with patients in their 80s trying to figure out what was wrong with me. Now that I know what’s up, and there’s no cure, I’m starting to get much more interesting now! Even though my core friendships go back 15 and 20 years, I’m meeting awesome people now who are amazing inspiration for us to develop the next (hopefully non geriatric) phase of our lives. So it’s rarely ever too late to learn unless you think there’s an expiration date on that.

    • I really appreciate your perspective on this. Like you said, people who luck into decades without disease can pull off some amazing things. That marathoner coworker of yours is a pretty remarkable case. I couldn’t run that far to save my life, and I’m in better shape than I’ve been in in a while. Happy to hear that you’re still making new connections. I agree that things like that aren’t time-limited if you decide they’re not going to be. Thanks for taking the time to share your experiences!

      • I should also add that in his late 20s, PiC (my husband “Partner in Crime”) decided to become a marathoner, and did! He’s had great health up til now, though, so his challenges were more normal ones like learning to eat well and training regularly. It’s harder for him now with a toddler but I figure he’ll be back in fighting trim in a few years. I highly encourage everyone around me to do awesome things like that, I’m good at cheering y’all on 🙂

        • Wow, I’m impressed! I joke every time I see a marathon happening that I had intended to enter, but once again, I forgot to train for it! Pursuing an athletic feat like that is somewhere on my FIRE to-do list, but I don’t know if I’ll ever go for it. It seems so physically impossible — but then I know people doing 100ks and ultra-marathons. Insane, but apparently doable.

  15. great Email!! My comment for the reader… I’m not sure I’d be concerned unless there is a family history of poor health in aging… This is coming from a 36 year old who is very active… I run 30-50 miles a week, I rock climb, bag 11K foot peaks, put on hundreds of miles in the saddle both road and MTB, Ski and Snowboard pretty much on a monthly basis… (The snow does disappear for about 4 months out of the year.. Other than that I do thing stuff on a weekly basis.. it’s just my lifestyle..

    I also still earn about $140K at my career job that I love… but I’ve learned to work with the flexibility I have there for time off to have fun while working.. Sure I’d love to quit… but I’m not there yet with my vision of FI..

    My point was… working 10 years while saving diligently will give you a lot of head way in terms of retiring at the end of that 10 years.. and your health won’t change much if you keep active now!

    • Great perspective, Tim. Awesome that you’ve managed to be so active, especially while earning a big income! That’s not necessarily an easy combination to maintain. Cheers to more years of good health!

      • I have been pretty fortunate and blessed to do what I do… but at the same time.. it really has been A LOT of work! But I live by the Work hard Play Harder rule.. so it fits with me..

  16. Mrs. Farmhouse Finance

    April 4, 2017 at 3:22 pm

    Great advice! It’s hard to know what your path in life is going to be when you’re 23, but it looks like Buster is already starting to figure it out. I think that it is a good idea for Buster to look for a job that is less soul-crushing. He could either pursue work that combines his interests in the outdoors (and probably not as much pay) or look for another good paying job to seriously start saving for early retirement. An adventure between jobs might be a good idea, but early retirement is probably unsustainable at this point. I know people who were ski bums for years after college, and are only settling into careers later in life (with the consequence of having to work much longer to save enough to retire), and people who worked hard for years to be able to retire early. Personally, I think I’ll enjoy the lifestyle more when I know that I’ll have enough money to sustain it.

    • That’s a good point, Mrs. FF: at that salary level, if I weren’t enjoying the work, I’d probably want to pivot one way or another — either toward passion-oriented work or for something that would put me on a faster track to taking time off. I agree with you that I enjoy the experience more knowing that I’ve built the financial cushion to support it, rather than always wondering how I’m going to fund next month’s adventure.

  17. Great advise! One other thing he could do is get a side gig at a rock climbing or mountain biking center. Make a little money on the side that you can save towards your future while doing something you love. The money will likely not be all that high but at least you would be doing something you love. This might also balance out your dissatisfaction with you current job until you can find a better more fulfilling full time job. I know we all want to be at our FIRE goals now but 23 is so young! You have so much time ahead of you to not only enjoy life but save money and get compounding interest working for you.

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