Beginning a new project always feels exciting. Whether it’s working on a hobby, learning new things at work, or pursuing FIRE, motivation at the start often runs high. But eventually the honeymoon period ends, and what was novel eventually becomes routine. Whatever it is that you’re working towards, the mundane and uninteresting aspects of that thing will eventually become the norm. And once we enter that “Boring Middle”, it becomes difficult to stay motivated, making it even easier for stagnation to creep in.
When you want to go from point A to point B as quickly as possible, every road you choose will have some sort of problem. Choose the slow path and complain about how you won’t achieve your goal soon enough. Choose the fast one and instead complain about how difficult it is.
To one focused on achieving goals rather than walking the Path towards them, the “Boring Middle” becomes an inescapable reality. A reality that the Keymaster—the avatar of our self-imposed entrapment—is more than happy to lock us inside.
So how do we overcome the discontentment of the boring middle? How do we attain the keys to overcome stagnation?

Life Update: Back to Work
Before we discuss that further, I’ll share a quick life update.
If you’ve met me at a FIRE event (either in Australia or in Bali!) you may know that I’ve recently returned to work. It’s a casual contract role where I have a large amount of freedom in how I complete assigned tasks. But it’s not gone as smoothly as I would’ve liked.
I’m working on some excellent projects with excellent people. And the work ensures my career skills stay sharp. Best of all, I largely get to choose my own hours, which gives me immense freedom over most jobs. It feels good to be back at work after 8 months without a job. But while this sounds good on paper, it invited in some bigger challenges.
I’m working casual hours on a system implementation project. As a result, my hours are extremely variable. As I settled into the role, I kept myself available at all times throughout the week in case I was needed. This approach backfired, and caused me to drop positive habits I had formed while I had more sovereignty over my time. Rather than planning my time accordingly, I simply made myself available to my employer, and neglected other aspects of my life (including my writing).
Having mastery of my time made me mighty, and is what I’ve focused on cultivating over the last 12 months. While I worked and kept my time free for work that might not eventuate, that mightiness began to diminish. For the first time in a long time, I felt as though my work was causing me to wither away.
This isn’t a fault of the work that I’m doing nor the people I work with. Allowing the possibility of work to control more and more of my time was entirely my own fault. And worse still, as my hours were ad hoc, I wasn’t getting paid either!
While the cold Melbourne winter didn’t help my habits, my issues stemmed more from inefficient time management than anything else. I fell into a stagnant rut as I readjusted to work. Thankfully, I’ve recognised the damage this was doing to me and have returned to the Path. But the effects of that stagnation have run deep.
Stagnation
When I wrote about stagnation previously, I described it as occurring when you do nothing over a long enough time horizon. By refusing to engage with reality for too long your health and wealth become ruined by entropy and inflation.
A desire to keep moving forward is necessary to solve the problems you have in your life. If you need money for food and shelter, you must work to earn that money. If you have a health condition (or age) that requires maintaining a certain level of fitness, then you must exercise. The actions you take should push you towards a better future for yourself (and ideally others). Slowing down risks losing momentum, opportunities, and earning potential, all of which make your future life much easier.
That said, there are times where pause makes sense. I personally went through this two years ago when I left my corporate career. After walking away from my job, I spent 6 months of my life rediscovering what matters to me and how I want to spend my time. The unburdening I felt on that final day of work was unlike anything I have experienced before. And the period of rest that came after helped me realign my approach to work, life, and meaning.
Of course, the pursuit of Financial Independence is what made this possible. But if you have faith in your skill set, resourcefulness, and network (plus a healthy savings buffer), you can “retire” from your career much sooner than you might think.
But stagnation doesn’t encompass every aspect of your life all at once. You can stagnate in some areas of life while progressing in others. During my career, I made massive progress towards FIRE, but my health and wellbeing suffered. Everything has a cost, and every decision you make has trade-offs.
A level of sacrifice is necessary to build your financial foundation early on. The law of compounding shows how saving money early on will earn more than dedicated savers can contribute later in life. Building a portfolio as soon as you can is essential for long-term success, as you can rely on it growing over a long enough time horizon. There are plenty of things to invest in for different reasons, and finding investments that work for you is just as necessary as stumping the funds to invest in them.
Life forces sacrifice, and you have to choose what you sacrifice wisely. The most important sacrifice you can make is avoiding excessive spending early in life. The compounding of interest on consumer debt alone will destroy your chances of building a comfortable level of wealth. And this is before you begin to unravel the need to overspend. But of course, chasing FIRE and letting your health stagnate only works for a time. Eventually, that stagnations begins to affect more than just one aspect of life.
Stagnation in the Boring Middle
Let’s say you’ve begun on the path to Financial Independence. You’ve developed your personal financial system and gotten debts under control. You’re saving, repaying, and/or investing diligently. All you have to do to solve the money problem is keep showing up at work while you build your portfolio… for the next few decades. Do you really have to do the same thing over and over just to watch the number on the spreadsheet go up?
This topic is often described in the Financial Independence community as the “Boring Middle”. While it appears as though you are making good progress financially, it leads to another form of stagnation. Yes, good things take time, and you can’t expect your life to change after you get your first dividend. But it’s easy to fall victim to stagnation as you enter the boring middle.
When you have created a plan that allows you to retire earlier, the motivation to make it happen early on is like a drug. Getting to a position where your financial position is comfortable and thriving is an incredible high, that only gets better as the investment accounts continue to grow.
The problem is that as the motivation fades and the money saved doesn’t make an immediate impact on our lives, it can cause us to lose that motivation. Eventually, even as the account balance goes up, we notice nothing changing around us. We slow down and begin going through the motions of working and stacking more investments. And we still don’t have the control over our lives we were doing this for in the first place.
We are all too willing to accept stagnation in other areas of our lives as we continue chasing market returns and filling up our accounts. Health and relationships with family can lag as the dollars keep stacking. Worse still, we avoid interacting with our investments, knowing that we need to reach our beloved 4% rule before we change our lives.
In this scenario, the game is solved and the pieces are set in motion. But you must wait for your number, your boss, to tell you that you are free. Blind pursuit of FIRE deifies your portfolio, birthing a god that you must pray to before it gives you the ability to live as you choose. You have chained yourself to your goal, and surrendered your freedom to the whims of the Keymaster. Is one truly free if their actions and beliefs do not allow them to live a good life every day?
Overcoming Stagnation & the Boring Middle
A few of my previous ideas come to mind when thinking about overcoming the Boring Middle:
Build Community
Community gives us strength. It is a powerful tool for building friendships, accountability, and support for one another. As the world marches towards an individualistic outlook on life, it can be easy to disregard the benefits of community. But they can offer both advice and opportunity.
Getting more involved with my local FIRE community has been a blessing. And the friendships that have blossomed from it have truly changed my life for the better.
If you’re pursuing FIRE and struggling to keep the flame burning, find people who are also on the journey. Whether it’s online or in person, knowing that there are people working through the same challenges you are is reassuring. Knowing you’re not alone encourages you to keep moving towards your goals, and learn alternatives that you may not have thought of.
Never Stop Learning
Continuous learning is an essential aspect of life. The world is constantly changing, and if you’re not moving with it, you are falling behind.
This isn’t a “hustle bro” idea. It’s just a fact. And if any part of your strategy relies on earning an income, investing, or any type of engagement with others, then learning is non-negotiable. You cannot expect everything you know to last forever.
Creating a lifestyle that rewards you for learning is the simplest way to solve this problem.
Be Bold
I wrote the majority of this article in a wooden hut on a small island called Nusa Lembongan in Indonesia. We’ve had no electricity for the better part of 12 hours, with an overnight temperature of 27C or 80F. And my poor laptop is almost out of charge!
In the moment I thought, “I wouldn’t have come to this island if I knew we’d have sweltering heat and no electricity.” But this is exactly why I should be here.
It’s very easy to get used to comforts from home. Reliable power and accessible drinking water are barely acknowledged in the West. It’s just an assumption that we have them, and one that’s very easy to take for granted.
Travel, new experiences, and doing things outside of your comfort zone require you to be bold. New places and opportunities broaden your mind and humble you, and put you in uncomfortable situations. But even if it’s uncomfortable in the moment, it’s better than never experiencing hardships.
As Seneca said:
Set aside a certain number of days during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while, “Is this the condition that I feared?”
How I Avoid Stagnation
The Third Journey is my personal philosophy of action. It demonstrates the steps I took to transform my dissatisfaction with traditional FIRE and live a slower, more intentional lifestyle. But discovering traditional FIRE is still a necessary step (it’s a large part of the “Second Journey” after all). FIRE teaches you that a life without mandatory work is not only possible, but surprisingly simple. All the strategies, stories, failures, hopes and dreams of those who’ve achieved FIRE are a testament to its ability to fundamentally change your life. And as I’ve learned from my time in Bali, FIRE can literally save your life.
Methods to transform your time from slave to sovereign are rare, and achieving the means to do so is difficult. For that reason, I believe solving the challenge of money should be the primary goal. Thankfully, modern conditions make it easier than ever to build and grow wealth. Knowledge of FIRE is therefore the key to the sovereign life many aspire to live.
The problem is that FIRE is all-consuming. Earning enough to fully FIRE can quickly become the focus, rather than living the good life that full FIRE promises. I can’t tell you “it’s not about the money” when to a point, it obviously is. But chasing FIRE leads people down the path of chasing money, rather than making positive changes to their life in the present. But discovering this fact is extremely personal; it’s a feeling that must be felt. Everyone in the FIRE space brings this up, and I feel everyone has to realise this simple truth for themselves.
This happened to me near the end of my permanent working career. After a tough period at work that ended fruitlessly, I asked myself the question: “what am I working for?”
After weeks of pondering that single question, I realised that I couldn’t even answer it. That was the moment I knew that my Second Journey was over, and when the Third Journey began.
You may find yourself in a similar situation in your career, and if you aren’t sure why you’re doing what you’re doing, you may need time away to figure that out. My career break gave me the time to understand exactly what mattered to me and is something I fully recommend doing.
Closing
Don’t allow yourself to stagnate with your old opinions and ways of doing things; be open to the possibilities of the world around you. Trying new things and learning from others is the secret to staving off stagnation and the Boring Middle.
Once you find a freedom that works for you, take it. That freedom will allow you to pursue whatever you desire and change your life for the better.
To stagnate is to invite chaos into your life. FIRE’s Boring Middle is simply stagnation given contextual form. And overcoming this stagnation comes to those who choose to change their life; those who choose to spiral upwards out of the Keymaster’s grip.
Thank you for reading.