It’s Not About Retirement Anymore

I'm at a fork in the road. Saving and investing is not about retirement anymore. It's about building freedom and flexibility into my life.

Traditional retirement is a suboptimal goal.

Building a career you genuinely do not want to retire from is better.

Writing those words here or in a 240-character tweet takes little effort.

But it’s an enormously complex concept for most middle-aged workers.

To say:

Hey, all you people aged 30-55, with kids, a mortgage, not-enough retirement savings, and perpetual life expenses — who don’t genuinely love the career path you fell into a decade or two ago — just build a career you love. Do that, and you won’t want to retire!

It’s not that simple.  

If 20-somethings can implement the “build a career you love” advice early, great. Experiment, pivot, and find the perfect match for your skill sets. 

But a mid-life career change is a major undertaking with significant extra effort and risk, on top of family responsibilities.

From that perspective, traditional retirement isn’t such a bad goal after all. 

Most workers will never love their careers. 

A career from which you genuinely don’t want to retire is an elusive luxury.

Financial independence is better than retirement.

Pretty easy to write and tweet those words too. 

Social media “gurus” throw these simple “pro tips” at us as if we can just make a quick change after lunch, and we’ll suddenly be successful, wealthy, and happy. 

Maybe it’s just my Twitter feed where 25-year-old money coaches offer definitive advice as if they’ve escaped the trenches and discovered the meaning of life three years out of college.

Just save and invest 90% of your income, spend nothing, and you can reach financial independence in like five years, bruh! #freedom $BTC

If you’re a parent with dependent children, be cautious taking financial advice from someone who isn’t.

About 63% of Americans live paycheck to paycheck, according to the latest LendingClub report (Sept 2022). 

Another 32% struggle to pay cash for a $400 unexpected expense.

Inflation makes each paycheck worth less, and credit usage is surging again.

Most people have limited funds to save for the future — let alone enough for financial independence

A random guru tweet or even advice from a trusted mentor will not change a financial situation.

Significant change takes massive shifts in habits, priorities, and increased earning potential.

Financial independence takes persistence and time — more than five years, bruh.

It took me about 20 years.

A Career You Genuinely Love >

Financial Independence >

Traditional Retirement

It’s taken me nine years of writing about money to understand this hierarchy.

Not that others haven’t said so already. Some of you have even emailed me about it.

We must come to our own conclusions before accepting something as true.

If I had understood the importance of this when I was 27 after backpacking around the world, maybe my follow-up career could have been more fulfilling. 

But I was too tied to my past and narrow-minded to forge forward more remarkably.

An IT career was the path of least resistance toward early retirement. I wanted to retire early so I could travel again. 

However, I realized that retirement travel was a long way off when we started having kids.

Indifference toward my career became the motivation to retire early instead of my desire for freedom and travel.

I chose a high-salary career path and considered job satisfaction a second-tier priority.

Each cubicle day validated that thinking.

I don’t regret my IT career — I learned and accomplished a lot and worked with great people.

I’m grateful for it.

The urge to retire from it motivated me to prioritize saving and investing. That led to writing about saving and investing. 

I’m now empowered to transition to a profession more aligned with my interests. 

It’s Not About Retirement Anymore

My Dad and I were fishing with my son and nephew a few months ago. I told him I was considering leaving my career to be a full-time blogger. 

His mind went to healthcare, “how are you going to cover health insurance for you and your family?”

COBRA at first (12-18 months), then probably the healthcare exchange. I’ve got time to figure the second part out. 

He paused. His second question was, “will you still be able to retire at 55?”

I said it’s not about retirement anymore, Dad.

It’s about:

  • being more available to my family
  • focusing on meaningful work that I enjoy
  • building on the nine years of effort I’ve put into my online writing business 
  • leveraging the saving and investing I’ve prioritized over the past two decades
  • prioritizing good health

I needed him to ask me that question because traditional retirement was a singular focus for a long time.

If I were to stay in my IT career for another eight years (I’m 47 now), I’m confident I could retire how I envisioned it in my 20s.

But eight years is a long time. 

I want to be a full-time finance writer now, not an IT professional.

And that’s what I’m going to be.

December 2nd, 2022, was the last day of my IT career — 189 days after my original target date. 

But this isn’t retirement.

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  1. Congrats Craig! You have done things right and I applaud your efforts. I have feared leaving my job (at 57 yrs old) due to the cost of healthcare and my lack of confidence in my ability to generate predictable income from my investments. I look forward to reading about your journey and how you overcome these type of obstacles, especially the healthcare. Thank you for all the good advice over the years.

    1. Thanks Dan. Healthcare is what worries Mrs. RBD. But we’ve budgeted for it, and I’m optimistic that we’ll find the right coverage once COBRA runs out. My son’s diabetes complicates things. But I consider it all a big financial equation. A lot of it is about confidence in my ability navigate this and trusting the numbers. I also want to be writing a lot more than I’ve been able to for the past few years, so there are many factors that have led to this milestone. I’m excited.

  2. Nancy Finney says:

    Wow. So much to say. I’m very happy for you and have enjoyed watching your evolution. I’m a 61 yr old CPA, CFO. Truly love my job. Between you and Tim Ferris’ “4 hour work week”, we started what we call “working retirement”. Negotiated more vacation, became an expert travel hacker w points and now travel a lot while working full time (in office)

    I also researched and began dividend investing, added a Fundrise account we contribute to monthly, reassessed everything over these past few years.

    Life is about seasons and there are many in life. Thank you for challenging my thinking and helping me become a better, more rounded, intentional person.

    1. Thanks for the many kind words of encouragement over the years, Nancy. I admire you for loving your job and aspire to say the same.

  3. EDWARD MILLER says:

    Congratulations! I have been following you since 2019, I have used your advice often! I’ll be done with this job after 33 years in March, I can’t wait. Too bad it took till 60 to leave, but life throws some curves. I’m thinking about a retirement blog of new places that I’ll be going to and taking up all the hobbies that I never had time for.
    Good luck with saying goodbye to corporate!


    1. Congratulations to you as well, Ed. DM me if you decide to start a blog and need some pointers. Starting my blog was a big step out of my comfort zone, but it’s be very rewarding.

  4. Congratulations! I look forward to your writings.

  5. This is so great, congrats Craig! Happy to see you taking the leap to the other side. It’s nice over here. 😉

    1. “The other side”, yeah it kind of feels like that. We’ll see if that holds a year from now.

  6. Raj Aggarwal says:

    Hi Craig, first of all congratulations on your journey. I have been receiving your emails for a while but never paid much attention till now. I full agree with you that it is all about financial freedom and not retirement. I will be paying more attention to your updates from now onwards!!

  7. It sounds like a great idea. I do not regret that I worked until I was 60 but that’s not for everyone. I also don’t regret the side gigs I’ve done in retirement though I’m mostly done with the ones that make me money. I think you know what you are doing. I look forward to reading about your new phase of life.

    1. Hey Steve, yeah I expect this milestone to open up some new topics to write about. I’ll certainly have more time to write and think about it. I’m grateful for my career and could even end up back there at some point. But even more grateful that I started a side hustle back in 2013. Life-changer for me.

  8. Nothing is forever, nothing is certain, so taking the leap now to do what you feel most fulfilled with while methodically covering your basis is a solid decision. There will always be a woulda, coulda, shoulda. Many people who left their careers to do something more interesting to them ended up making more money with it in the long run anyway.

    1. Thanks DGI. I couldn’t do this if it weren’t for the dividend income I’ve been building since 1995. Definitely gave me some confidence to consider career alternatives. Not planning to sell any of those holdings, just collecting and reinvesting.

  9. Good for you guy! If you’ve got no regrets about quitting than go for it! There’s plenty of money in writing for your cash. Plus the amount of free time you can get that’s a bonus! I’ve got 5 years to go and I can retire from my city job. I’m counting the days with excitement. Can’t wait to read about your next adventure. Enjoy sir.

    1. The only thing I would have regretted was not doing this. Even if this doesn’t work out, I will be pleased I gave it a try. There’s a Jeff Bezos quote floating out there about what you will regret when you are 80-years-old. It’s not the failures, but the things you never tried. I’ve thought about that quite a lot over the past few years. Good luck over the next five years earning your freedom.

  10. Nine years, hard to believe I’ve maintained this blog for that long. I’ve tailed off a bit in the past couple years, but now I can focus a lot more attention on it. And hopefully, the extra time will enable better writing and more thoughtful topics.

  11. I agree with all your points in this post. Especially this: “If you’re a parent with dependent children, never take financial advice from someone who isn’t.”

    Also, congrats. I pulled the plug on my longtime career at the end of 2021 and don’t regret it for a second (even if I do wish that our investments were having a better year ;-))

    1. Hi Fi for the People. I hope I can “net positive contribution to society” that is less questionable than yours 😉 Enjoyed your About Me.

  12. Congrats, Craig. I had to smile at your response to the insurance question. That was exactly my position when I decided to retired (COBRA for 18 months, then I’ll figure it out), and it worked out fine. Life’s too short to keep working strictly for the security of employer-provided health insurance. There are options out there, and you’ll find them. Sincerely happy for you.

    1. Ha ha, yeah I think I took that from your playbook! I read those posts and I know you put a lot of time into the decision. It’s funny, I have this friend who is self-employed and so is his wife. When I told him I was apprehensive about doing this because of health insurance, he was like “what, why would that hold you back. Just buy health insurance.” He’s never had an employer and just bought it for the family. I’ve heard that echoed other times. My COBRA will be expensive because it is very good insurance. But I’ve factored that in and I’m ready for it. Hopefully, we’ll find something almost as good and cheaper. If things really don’t work out, I can always go back to work.

  13. Congrats! After I “retired” from the military a few years ago, I had no idea the benefits being……so beneficial. Namely healthcare. I’m also in my 40’s and have been toying with the idea of full time “retirement”. Congrats to you and thank you for posting what you post. You should know you help a great deal of folks.

    1. Military retirement benefits are a good deal. You’ve earned it, thanks for your service. Also thanks for the technical issue you found on the website.

  14. Congrats! While our goal is still some version of FI/RE it’s really about the optionality and that’s what your diligent saving/investing over the years has provided you. Many people, especially once they have a spouse and kids, literally can’t afford to take a risk like you’re going to do but you have that choice. I’m seriously considering some different options that had we not began down this journey there’s no way we’d be in a position to even consider it.

    1. Thanks JC. You were one of the inspirations when I started this blog in 2013. Still can’t believe it’s been nine+ years. I haven’t been reading and commenting on other blogs like I used to, hopefully this new situation will enable that. Good luck with deciding on your next steps if you take that plunge. Certainly ping me any time if you want to bounce ideas.

  15. The Bludger says:

    Hi Craig – congrats and best of luck!

    I agree with your hierarchy! But the issue I have is knowing what I want to do, I flip from wanting nothing to wanting to do everything!

    Once I start looking into new careers – there is always barriers (training) or risks that make it seem way to difficult.

  16. I retired 2 years ago at 50 and went with Cobra until it expired. Then, I signed up for ACA. If I could do it over again, I would have jumped on to the ACA sooner especially since it was still open enrollment. My deductible on Cobra for a single person was $500 deductible and costs $880/month and I hardly ever go to doctor. My ACA plan is $100 deductible and $175/month with premium credits or $660/month without any credits and all my doctors are in same network. Don’t be scared to try it out. I wish I could have saved thousands by not going to Cobra route. The Dental/Vision on ACA is just as good for a few more bucks per month than my employer.

    1. Thanks for sharing your experience. For us, going to COBRA is meant to help smooth the transition so there aren’t any other major changes. Mrs. RBD did not want to deal with an insurance change, especially with our son’s diagnosis. We are paying for a family of 5 which is considerably more expensive, and we are always going to the doctor for illness or whatever. My son has very high expenses for insulin, insulin pumps, and CGMs (continuous glucose monitors). So we hit our deductible very quickly. I’ll certainly take a close look at the ACA marketplace during open season and move over if it makes sense. But COBRA is best for us at this stage.

  17. Congrats Craig Love that you are doing what works for you and your family. That’s what I continue to tell my children everyday. They both get it and know to do something that is rewarding and not always a safe option. I do believe in financial security. As a woman that ranks high for me. I have been working 21 years at a government job (pension and hefty savings account) that’s what makes me feel safe an secure. I do not need to work any longer however, I want to. That was my turning point. I am glad you have made an informed decisions for you and your family. Do what works for everyone you love and care about. You are correct in that if it doesn’t work anymore you can always pivot again and make another change. Nothing is set in stone.

  18. The ending to this article gave me goosebumps. The way you write makes the material so relatable. Congrats!