Do You Desire Freedom or the Pursuit of Freedom?


I had lunch with a good buddy today. Now that I’m on a leave of absence, I’ll admit that I’ve gotten into too much of a groove of doing things solo again; I’ve resorted back to my introverted tendencies, which is something I don’t necessarily want to indulge in. Being around people is a wonderful thing, and today’s meet up was a reminder of that.

As usual, we cracked jokes and talked nonsense for a good portion of our meet up. But at some point, the topic of financial freedom came up some interesting points were made. After some time, I commented to my very successful friend, “You know you’ve already won the game. You could retire tomorrow and live out the rest of your days in great comfort. Your house is worth well over $1MM and it seems to keep getting more and more valuable with each passing day.

My friend thought about this for a moment, before answering back with the ultimate deal-breaker:

Yeah, but I don’t want to move someplace else. I like it right here in the Bay Area. I want to stay where I am. And if I sell my house, I won’t be able to buy something similar for much cheaper. And the cost-of-living (COL) is so high…

This comment left a mark on me… and it made me think about many things. For starters, we are absolutely dealing with some serious first-world problems here! Even if we kept things within relative distance, I’m guessing the majority of people in this country would marvel at what a “lucky son of a gun” my buddy is to even be in the position that he’s in. How many of us could have reasonably expected our homes to appreciate by over $700,000 in less than a 15 year period?

When Luck Gets Us

Human beings are very interesting creatures. For starters, we are all highly adaptable and can adjust to many different scenarios. Economic booms. Recessions. Great Recessions. Regardless of what the world hits us with, we always find a way to bounce back and persevere onward.

Forward march.

But in the process, do we take for granted our blessings? As a freedom fighter who has been on the journey since 2012, you could say that financial independence is something that’s on my mind a lot… I’ve dealt with all the emotions and hurdles that come along with taking on such a massive life challenge; there have been many ups and downs along the way:

Joy. Frustration. Anger. Heartbreak. Euphoria.

In a sense, because the goal of financial freedom isn’t easy to obtain, it makes me push that much harder to achieve it. But what if, instead, it all magically fell into my lap at the very beginning, without the struggle. Would I still appreciate it just as much? Would I still go through with my conviction and quit my job on the spot? Or would my thoughts and actions be the antithesis of everything I’ve been writing on this blog over the last few years?

The question becomes: Do you truly desire freedom, or the pursuit of freedom?

A Different World

I still vividly remember when I was starting out my engineering career and the Great Recession hit. In an instant, most everyone’s retirement account balances were reduced to a fraction of their peak values. One gloomy afternoon, I happened to stumble into my manager’s office, and I can still recall the intensely perplexed look on his face:

Can you believe all this bullsh*t going on in the market lately? Look at my account balance, it’s all gone! Looks like I’m not going to be retiring early like I had planned…

When things get tough, people find a way to knuckle up and get things done. We get more creative. Resourceful. We work harder. We burn the midnight oil. We basically do everything that we can to overcome what feels like an insurmountable obstacle.

Along the way, we lament in all the things that we should have done:

  • Why was I so greedy?
  • Why didn’t I sell earlier?
  • Why did I stop paying attention to fundamentals?
  • How did I not see this coming?
  • I could have retired!!!

We vow to ourselves that we will never let this happen again. Greed will never control us again and we will instead count our blessings everyday. More importantly, we won’t let something as fragile as financial freedom slip away from our grasp again…

A bird in the hand is worth two in the bush.

When times are bad, and there is doom and gloom in the air, we tend to learn many things… But when the tables turn, and the pendulum swings back the other way, do we end up not keeping our very promises?

What Do You Really Want?

Fast forward to present day, and times are good again. Yes, my manager is still working. Although his portfolio and assets have recovered in value, I really doubt that he plans on quitting his job anytime soon. Ditto for my good buddy, even though both gentlemen easily could today, if they wanted to.

Which makes me tend to believe that true financial freedom isn’t what everyone ultimately wants to achieve with their lives. Even if they say that’s what they want, I’m starting to believe that it’s the pursuit of financial freedom that drives people to do the things that they do.

And that’s understandable… Human beings are resilient, but they also desire structure in their lives. No matter how much you claim to covet financial freedom, it’s a drastic life alteration to just wake up one morning and sever ties completely with a routine that you’ve been practicing for the last many years of your life.

Drastic change is not for everyone.

Also, most people just want to be comfortable. So, even though everyone says that they would retire right away if they won the lottery, I highly doubt that most actually would. And it might be surprising to learn how many early lottery millionaire retirees inevitably end up back at work…

How You Can Tell

How can you tell if it’s freedom you want, or simply the pursuit of freedom? Well, how about putting together a list of all the activities and hobbies you would pursue if you somehow found a way to free up 8 additional hours each day? Does the thought of ditching the 9-5 routine make you feel all giddy inside? Does your heart start racing at the thought of all the new possibilities that will open up for you? Can you easily get lost in daydreaming about the many hundreds of different places you’ll be exploring outside the cube? Does absolute control over your time and day mean sooooo much more to you than where exactly you live (geographic arbitrage)?

If so, it’s probably TRUE freedom that you want!

But if instead, you look for excuses and come up with a laundry list of reasons of why you still can’t retire early…

  • But I still need $X more…
  • But the cost-of-living (COL) in Location Y is too high…
  • But what about medical bills?
  • But my pension isn’t ready yet…
  • But what if the market crashes again?
  • But…

When it comes down to it, if you truly desire freedom, you will take action and make it happen sooner rather than later. You’ll kind of have to… because the thought of working for many more years is something your body can’t process or comprehend. The burning desire to do something else cannot be tamed or extinguished. Even if you don’t currently have all the answers, you just know in your heart of hearts that you’ll figure out a way to make it all work… You want freedom that badly!

On the other hand, if you need to get all your ducks lined up in a row first, you’ll probably end up playing the “one more year” game for perpetuity. That, and deep down, you probably don’t hate your job as much as you might think… And that’s all perfectly fine. We all have to move at our own pace… and some of us are more conservative than others.

Like my old boss and good buddy.

When times are bad, they’re working. When times are good, they’re still working. Yet they talk about how blissful absolute freedom would be…

But if they really wanted it THAT BAD, and they could make it happen…

Wouldn’t you?

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No Nonsense Landlord
5 years ago

As someone who could leave today, and have a near 100% certainty of living as good, or very likely better than I do now, I am going to put in the proverbial “One More Year (OMY). It’s better to lay a solid foundation while you can, because after you leave the workforce for a few years, it’s minimum wage jobs when you come back. I am a technical worker, similar to yourself. You cannot go back to a technical job after a few years of being out. You will be either too old, or your skills out of date. Make… Read more »

5 years ago

To echo off landlord,

Suppose one of you wants to build a house. Won’t you first sit down and estimate the cost to see if you have enough money to complete it? For if you lay the foundation and are not able to finish it, everyone who sees it will ridicule you, saying, ‘This person began to build and wasn’t able to finish.’

5 years ago
Reply to  FI Fighter

I forgot to put quotes. That was a saying a very famous man said. The point is let us prepare for the future and not go forward without a plan. You have successfully created a plan and are living it out.

We could all be so lucky

Reply to  Mark


At leat give credit to the scripture of the Bible you’re quoting from……

Financial Samurai
5 years ago

Great point about making hay while the sun shines. If the economy was in the dumps, I definitely would NOT be spending time consulting elsewhere as I have for 1.5 years.

The one more year syndrome is strong, and will capture the best of us. It’s hard to break out! I wrote a post exactly about overcoming the “one more year syndrome” to help people take a leap of faith.


Dividend Hustler
5 years ago

Hey FIF. Great article. Thanks for sharing. These friends of yours are in a great position and I’m guessing they wanna build up as much as a nest egg as they can before they throw in the towel. There’s usually more to the story which we don’t know about. For myself, when I reach my number in passive income, I’ll cut back and work part time. I’d like to spend more time with the family, do fun things and relax more. Work out especially. I’ll always work though if not at my business, I’ll manage the portfolio and I will… Read more »

5 years ago

Hmmm – I think people are at different places in life. Personally, I’m planning on keeping my home in the Bay even if I decide to move away and rent it out. It was a major reason why I wanted to buy a home in the first place here so that I’d always have the option of returning. For a long time I realized I could go other places, but in the past when I’ve traveled I’ve always wanted to return home. I’ve been fortunate that my family has been supportive of this and provided me with a place to… Read more »

5 years ago

Well said Fi Fighter!! Put me in category 1 of people that are striving for FF and really want it. I love what I do, but feel like the idea is flawed that you have to work at a JOB until your 60s or 70s and pass up on incredible opportunities along the way to travel or spend time with family, or build a canoe. Sure, have a back up plan, but at some point, that back up plan will be so strong that you really can pull the plug on work. Yet, people think they still have to work… Read more »

The Professor
5 years ago

Good article. I’m definitely in the pursuit of freedom camp. I would get too bored if I retired.

Financial Samurai
5 years ago

Hi FiFighter – Is your leave of absence paid or unpaid?

One of the hardest things to do is walk away from high pay. The only way I could do it is if I was able to negotiate a severance package to walk away. That’s what my catalyst was, otherwise, I would probably still be working!

5 years ago

I think having no structure to daily life would be a huge and difficult change. I could imagine doing that for a short period like 6 months or a year of being a nomad just traveling and exploring. But at some point I would want some stability again. I’m not talking about going back to a full time (or more) job, but maybe a part time volunteer position where you do something positive or help people and make a real difference in some peoples lives. I think the key would be maintaining some sort of structure while still having a… Read more »

Midwestern Landlord
Midwestern Landlord
5 years ago

In general, it is my belief that if people are working, a majority of time it is due to the fact that they still need the money. For the few that could technically retire but do not, it probably boils down to timing, goals, positive work environment, perspective, etc. Maybe they have a highly compensated job and it is hard to give that up? For me, my driving desire from day 1 was to become financially independent and have control over my day. That was more important than continuing to work and pile up more resources. Time is a resource… Read more »

5 years ago

Very interesting article which made me to look in the mirror once again and made me stronger to pursue what I always wanted to dream of. Until then, I won’t stop.



5 years ago

Well said FI fighter!

We are all excuse machines (at least I know I am), where there is always another hurdle to throw in front of yourself before you can make the commitment. Its kinda like having kids….you want there to be nothing be green lights ahead, but that just never happens. You’ve just got to trust that its there and make the plunge@!