Leaving the Workforce at 29: Where Do I Go From Here?

Posted by Madison on August 19, 2008

I focused on early retirement my whole adult life. Whether it was hanging out at the Early Retirement Forums the Retire Early Home Page, the old Motley Fool Retire Early forum or the Vanguard Diehards Forum, contributing crazy amounts to our retirement plan, managing our asset allocation, or creating retirement checklists, I always had one goal in mind: exiting the work force.

I have less than a month until the big day and I’m panicking. I can’t quite describe the exact emotion, it’s a mix of anxiety, sadness, fear, and doubt all rolled up. It’s almost a feeling of emptiness.

This isn’t about missing work, it’s about changing the entire way that I align our personal finances to meet our goals. You see, ever since I was 16 personal finance has been one of my favorite hobbies. I’ve had lots of mini-goals, but all of them centered around the main goal, quitting the work force.

What happens after you meet your goal?

The problem is that I actually met my goal, the big one. And now that the excitement has worn off, I feel really disappointed.

I hit the “personal finance peak” and now I’m getting ready to head down the other side. Over time, I’ve found comfort in the climb up the hill. I know how to save money, live frugally, navigate retirement plans and taxes… but what I don’t know how to do is live the financial life on the other side. I’m sure it will come with time, but right now the feeling is a bit scary.

I’m happy and excited about my new life. Of course, I’m going to enjoy what I get to do with all my time – my kids, family, and other interests I haven’t had any time for. That part doesn’t concern me. It’s the relationship with money that is changing.

Where Do I Go From Here?

Obviously, I’m going to stick around here and continue to write about the stuff that made the climb up the hill successful, but I’m a planner, so I’m trying to come up with a new “goal” to replace my old one. Feel free to give me ideas…. I’m all ears.

Lots of times in our life we deal with transition. Maybe my way of handling transition is to make excel spreadsheets with lots of columns and dollar signs. I just don’t know what the column headings should be…

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Comments to Leaving the Workforce at 29: Where Do I Go From Here?

  1. How about some fun goals? Buying a vacation home, taking a trip… putting the kids through college (maybe not so fun). Or, non-financial – learn a new language, learn to garden, learn to bake…


  2. I just found you blog and Congratulations on your goal! Are you retiring from your full time job at 29 years old? Amazing! I would love to find out more. I’ll check out some of your other posts and look for the details.

    I also look forward to setting goals and think you should set a new goal for yourself. Maybe you could mentor someone else that is under 30 and help them reach this similar milestone. I’m sure you friends are asking for ideas all the time. Great job!

    Scott @ The Passive Dad

  3. Congratulations!!!

    Take a well deserved vacation and then, maybe, mentoring others on a one on one basis, becoming a life coach, would be a great new venture! You would still be setting goals and would still be planning. It would just be a different set of circumstances.


  4. Incredible job. I hope I can replicate this at a young age!

    Have you read the Four Hour Workweek? Ferriss has a good chapter or 2 on this.

    It’s got to be a tough transition for sure, but it’ll be 110% worth it. You are young and liberated- you can do a lot of really meaningful things that you’re passionate about without the typical constraints of the daily grind.


  5. Congrats! I would love to be where you are; it’s very exciting! I don’t really want to retire, but I would love to be in a place where I work for pleasure, not neccessity.

    I have a feeling your kids will be able to suck up a lot of your newfound free time. 🙂

    You could also take 20 minutes and brainstorm 100 things you’d like to do before you die. Then you can put your spreadsheet jones to work to analyze the data and start working towards them.

    Sara at On Simplicity

  6. Really inspiring stuff Madison! Congrats again. I would like to hear more about your cash flow situation. Has your side income grown to the size of your “regular job” income? Do you have contingency plans in case business income turns south?

    Million Dollar Journey

  7. Wow, all I can really say is “congratulations!” — that is quite an achievement. I doubt you’ve really hit your “personal finance peak”, though, and look forward to what you decide your next goal is.

    Richard @ Student Scrooge

  8. How inspiring! I wouldn`t be ready to retire yet, either (I`m 28), but you hit your goal, now it`s just time to make some new ones. And just because you are retiring from one thing doesn`t mean you can`t do another. Like the coaching mentioned above, writing or really anything you like! Start a small business doing what you enjoy and you can sell or walk away from anytime.

    But I agree with the above poster who mentioned that your kids will take up a lot of time! They will love to have more time with you, so take advantage of this time while they still want to spend time with you.


  9. Great goal of getting out of the work force. Many more people should make this a goal. There are many ways of making a substantial income from home.

    Mark Nelson

  10. Let me see if I got this, You accomplished your goal of retirement at 29, you are financially secure, you have no issues with family, friends, etc. Okay, hmmm! I read the post again and this is what I got, you made the biggest mistake goal setter make and did not plan for life after the “big goal” is achieved.

    Okay I got it, simple solution, set the next big goal. You are only 29, keep in mind that everything going well you still have another 50 years at least ahead of you. So I will tell you what to do.

    1. Relax and enjoy the success of your big goal for a week or a month, how long is up to you. Congratulations.
    2. Take that time to discover your next big goal and then go for it.
    3. Take the word disappointment out of your vocabulary, you have accomplished what most people spend their entire lives trying to do and many people don’t accomplish. Be proud and grateful. I don’t know you and I am proud of you.

    Okay, I did not expect to go big sister on you so I will stop now, I had a lot more to say, including putting you in a headlock but I have to stop, since you don’t know me either, but since you asked and since I know what it is like to not have the next big goal lined up before you finish the current one, I simply could not help myself.

    So take doubt and fear out of your life, you spent your 20’s living like a person in their 30’s and 40’s you are already a fearless person. Take care with all those negative emotions you have no reason whatsoever to dwell on them, please please, please find something new quickly and I know in another few years we will be reading something great about you.

    Only you can know what your next big goal is, as long as you love it you will be great at it.

    I hope I wasn’t to harsh, in the event that you feel I was, please feel free to delete this comment. But congratulations and keep up the good work.



  11. Achieving one goal motivates you to set new much more challenging goals.
    Now it’s time to think what you really want to do with your life, not just what you have to do to survive.


  12. Way to go retiring at 29! I guess investing early does pay off after all..

    What’s your next goal in life?

    Online Dividends

  13. Actually, I totally understand what you’re feeling. I went through the same thing last year, at age 47. I had spent so many years preparing financially, that it didn’t dawn on me until a few months before the “big day” that I’d need some new, not-necessarily-financial goals.

    I started a list of things I wanted to do when I had more time. That helped somewhat with the “now what?” feeling. I decided to list everything I thought I’d like to try or spend more time doing, without constraints. It pleased me immensely that all but one of them were either free or very low cost.

    Be prepared for some mixed feelings when you leave, too. I still feel a bit of sadness over missing my long-time coworkers. Not enough to go back, though 😉


  14. Congrats on reaching your goal! That really is amazing.

    I agree with The Passive Dad, I think you should mentor someone else with the same goal. You probably have tons of advice and encouragement to give someone else who’s striving for the same thing.

    Good luck!


  15. Well I didn’t start saving for any goals until I was twenty nine.
    I highly recommend you go enjoy your youth before you lose too much more of it.
    What good is money if you have no happiness to enjoy it with.
    When you are in your fifties and sixties, you want to be able to look back and laugh at some of the more crazier moments of life.
    Obviously you got discipline and direction but I am sure once you cut loose a little bit, something will come up that you might want to delve a little deeper into, whether its a business or another job etc.
    All the money you have can be lost and regained, but your life happens but once.
    Who knows, maybe you can teach some kind of guidance course on money management.
    We all know how poorly our educational system does that.
    Spread the knowledge.


  16. That’s pretty impressive.

    I am curious how your financial plan looks like for 50 or more years of retirement. How does one even deal with things like medical insurance for the long term? How does your plan look with a potentially expanded family? Are your assets in accounts that you can draw down on without tax penalties or mostly in retirement accounts with tax restrictions?

    So many questions…. but, congrats. I’m impressed.


  17. Congrats! Very exciting. I’m new to your blog. Very good stuff.
    Good luck!


  18. Funny enough, as I started reading this article, the song “Where Do I Go From Here” by England Dan started playing on the radio.

    Jonathan B.

  19. Congrats! I’m open to being your project i you’re in need of one. There is NO chance that I can retire at 29. I’m 5 years younger than you are with about 100K in debt, mostly in student loans and I feel trapped in what will be my first job out of school earning less than half what I anticipated when I entered grad school. I kid you not, my hair has actually all fallen out as a result and my sleep has suffered greatly.


  20. Congrats! It seems that we are living parallel lives. I too recently left my corporate job, I’m 28 and I too have obsessed about retiring early since my late-teens. 🙂 Nice to meet you!

    Keep up the awesome content. Feel free to drop me a line to say hi, anytime.


    Tina Su – Think Simple Now

  21. First I must say congratulations.

    My first thoughts

    Idea 1

    Help others in need of financial help for a small fee. With the money you can travel around to high schools middle schools within your area. For free mentor the young adults that are serious about retiring by the time they are 29, see them to their goal and teach them to do the same thing you did for them.

    Idea 2

    Stand up for the people and try to reform the credit system.

    The credit system as I see it is a major problem and favors big business and punishes the consumer, I would even say it is anti-capitalistic. When I was 18 I bought a new car, the dealership wanted 18% interest (yea right), a different company that I applied for on the internet wanted 12% (no way) and then I applied for a loan at a credit union, got denied, asked why and it was because of recent inquires. I explained the inquires to them and they gave the loan for 7%. I was being punished for looking for the best rate. Shopping around decreased my credit score and almost cost me thousands of dollars in this case.



  22. Well done. You should be very proud of yourself. I’m not sure the goal, for most of us, is simply to exit the workforce, but to have the freedom to do the kind of work we find rewarding, whether we need the money or not. Best of luck!

    Stock Research

  23. Thanks for all the thoughts! I’m currently doing exactly what Tabs suggested: Relaxing and enjoying the success of the big goal. I’ve been off work for a month now, and I haven’t felt any absence of a goal!

    Once I get used to it I’ll work on a list like Retired at 47, Sara, and a couple others suggested. Stay tuned!


  24. I am very surprised to get to know this blog
    or you, Madison.

    I thought I was the only one. I have, apparently, exact same story as you do, same
    methodology and surprisingly same EXACT outcome. I was working since I was 20 and
    I had the privilege to be financially free
    when I was 27. I am 29 now, and even though
    I am financially free, I have decided to
    keep working, not out of necessity rather
    out of having fun at work.

    It is a privilege indeed to have the power
    to retire early in life.

    This is my suggestion for you, the things
    that I am doing myself right now:
    1. To check your true passion
    2. To find your destiny in life. What do you
    think the creator on this life (if you
    believe in one) wants you to do in this
    life in accordance with your talent
    and passion?

    I would share my “destiny” to you, hopefully
    it can help you. This is little bit heavy
    to most people, but I think you will be
    able to handle this since you have proven yourself to be able to set yourself free by the age of 29. Congrats and I am happy for you.

    Personally, I want to impact the world,
    I want to become one of the Billionaire of
    the world, not for fame, not for money,
    not for power, and not for other selfish reason, rather so that I can use the power
    of money to help other people to become
    better in their life, to help the sick,
    to build hospitals, to build schools in
    third world country and for other things
    that I enjoy in life. I personally have
    this vision since I was 15 year old.

    To do this I plan to build a holding company
    in the order of Berkshire Hathaway. This
    company will be cup holder by which all of
    the required cash flow for all the charitable
    efforts that I dream of comes from.

    I plan to build generational wealth rather
    than individual wealth. I want to pass this
    company, the money, the vision and the dreams
    to my children, my grand children and my
    grand grand children.. except of course, I have
    to find a wife first before I can have
    children :)….

    Anyhow, I hope my writing will help you….
    Again congratulation for your achievement.
    I am happy for you and your family. You’re
    about to enter a tremendous exciting
    adventurous journey to the rest of your life,
    enjoy 🙂



  25. Can I be honest? I’m having a tough time understanding how you reached this goal so early. I realize that there are limits to what you want to say in terms of actual numbers about your finances. But when most people speak of being retired they speak of needing to actively work for income. Seeing as under typical rules of thumb it takes 1 million in investment assets to produce 40K a year in income, I’m struggling to know how you reached your goal. (I must admit I haven’t read your whole blog yet.)

    So some questions:

    1) Do you and your spouse have a pretty low expectation level of what you need annually? (Nothing wrong with that. I know folks who live admirable lives on 25K a year. I’m just curious as to what you are expecting)

    2) Do you pay for any expenses out of your husband’s salary or income from this blog?

    3) Did you benefit from an inheritance or timed a boom stock or timed the real-estate market?

    I don’t mean to be skeptical. I share your early retirement goal. But given that most of us can’t touch the money in our 401Ks/IRAs for a long time unless we want to suffer tax penalties or have it run out way in advance of us dying, I have a tough time believing you have really saved up enough assets to retire early at this age, unless you got a bit lucky. Saved up enough to maybe change to a more enjoyable job, etc. Sure. Especially if you are making a nice income from this blog; self-employed retirement accounts can be quite advantageous.

    I hope you don’t mind the skepticism. But as someone who has crunched the numbers a lot, something seems quite off here.


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