An Overthinker’s Guide to Making Life-Changing Decisions

Getting out of despair and learning to love life - Part 2

Read Part 1: How I Avoided Getting Killed and Killing Myself

It’s uncomfortable to admit that you’ve been a scared person for most of your life. Scared to take your life into your own hands. Scared to make any decision on your own. Always waiting for someone else, or life itself, to choose your direction for you.

That was me.

But how does one go from being such a timid creature to making life-changing decisions on his own?

How does one go from being paralyzed by insecurity to quitting his job, moving to the other side of the world, and betting on himself to make a living with his passion That’s what I want to talk about because that’s the journey I took.

However, this is not going to be “5 steps to go from insecure overthinker to master of your life” type of essay. Not every story can nor should come with a clear action plan.

So if you started reading expecting an actual step-by-step guide, well… I hate to disappoint you, but this is more of a field report from someone who walked his own path—and wants to help you walk yours, not follow his.

As you read, I suggest you look for patterns that are bigger than my story and can be applied to everyone's situation rather than focus on the specific decisions I've made.

Essentially, this is a story about taking responsibility for the finite experience that is your life and making independent, authentic decisions for it. How similar or different your life and dreams are from mine doesn’t matter.

To save you time, I won’t give an introduction to who I am and why I’m writing this series of essays all over again. You should read the first essay for that.

In 2021, I made multiple life-changing decisions. Not life-changing in retrospect but at the moment of having to make them.

Each time, I had to sit with myself and make a decision with full awareness that it was the single most important decision of my life up to that point.

In January 2021, I declined a promotion that I’ve been working towards for years and which would solve all my financial questions for life before I’m 30.¹

In October 2021, I decided to quit my job and restart my life on the other side of the world.

Soon after, I had to decide how I would make a living, which would then inform me where I would move. Although I didn’t have many attractive options, I chose the most chaotic and unpredictable one - trying to make a living from my online writing with no safety net or plan B.

My past life - Air Traffic Control

The first two decisions might seem like no-brainers if you’ve read the first essay and have gotten familiar with my situation.

If there was potential for my life to be in danger, of course, I was supposed to refuse the promotion that would tie me to my country for the next 6 years.

After I found out that my life definitely is in danger, of course, I was supposed to quit my job and leave my country. That’s the only thing that makes sense, right? If anything, I should’ve left sooner.

Well, wrong.

You need to understand that, in Montenegro, plenty of other people in situations similar to mine decide to stay. They decide they would rather spend their life having to look behind their back for a gunman than have to start again from scratch.

It would take a whole other essay or a book to dissect the Montenegrin mentality and how it has been shaped by my country’s history. But it’s enough to say that, as common sense as my decisions might seem to you, they weren’t so common sense to me or most people around me.

But it’s not just that these were difficult decisions as they were. I’m not sure I ever made a single independent, fully authentic decision up to that point in my life.

So, what happened? How did I gain the confidence to make these decisions and not be paralyzed by the fact that they are life-changing?

Looking back, I had already been preparing myself for these decisions in the months leading up to them. Those who have been reading my work for a while might notice a shift in my writing during 2021. I went from obsessing over philosophical texts and writing in a more abstract and intellectualized way, to focusing on the importance of making decisions and taking action in the face of uncertainty.

To my fellow philosophy nerds, it probably seemed like a move away from the depth of my previous topics. But for me, there was nothing deeper—nothing more serious—than finally engaging in my life. But I was writing to myself, trying to push myself toward the very decisions I had to make.

I was beginning to grasp something I had long resisted—the idea that life doesn’t grant you clarity before you act. That waiting for certainty is an illusion. I was starting to understand that action itself generates clarity, that the only way to get feedback from life is to step forward and make decisions.

I was beginning to grasp something I had long resisted—(self)knowledge come from engaging in life, not the other way around. Action precedes clarity and confidence.

“Decision is the little magic word that existence respects.” - Søren Kierkegaard

Life gives you feedback when you make a decision and take action on it. You get to observe how your actions play out in real life. If you’re moving in the right direction, you keep going. If not, you course-correct. To think that you can perfectly analyze and understand your situation before you make a decision is an overestimation of the power of human reason.

Today, this is the idea I’m most “famous” for. When I interact with my readers, so many of them say that “life gives you feedback,” “action before clarity,” and “jump into life” is exactly what they needed to hear when they came across my writing.

The decisions I made in 2021 felt like my first real leap into life. But, as I would later come to learn through deep suffering, I hadn’t committed fully to this leap. Making a few major life decisions doesn’t exonerate you from the responsibility to continue using your human freedom to make decisions and shape your life. Once you jump in, life doesn’t stop asking you to choose.

At the time, though, I knew that something in me had shifted. For the first time, I wasn’t just thinking about life. I was participating in it. That shift led me to the next question: How do I make decisions that are true to me?

I didn’t expect to learn how to make “the right decision” every time, but an authentic one. If I’m going to make a mistake, let it be my mistake.

That’s when I started caring about my soul.

Me caring about my soul isn’t a religious statement, at least not in the conventional sense. I didn't make these decisions thinking how they would influence where my soul goes or how it’s treated in the afterlife. I’m not criticizing or opposing those who make decisions that way. But I didn’t.

I’m talking about the soul as (almost) synonymous with the psyche. I’m talking about the soul as something affected in this life by how you make decisions about your life.

I’m talking about the soul as something that, if neglected, manifests its deterioration in the form of psychological and spiritual suffering.

The idea that transformed my life, the idea that got me to start taking care of my soul, is that a life of inauthentic decisions, which usually stem from fear, leads to spiritual, psychological, and emotional degeneration.

As Abraham Maslow wrote, people who ignore their destiny, their call in life, and their capacities, "perceive in a deep way that they have done wrong to themselves and despise themselves for it."

“I have frequently seen people become neurotic when they content themselves with inadequate or wrong answers to the questions of life." Carl G. Jung

“Fear is unavoidable, but a life where fear calls the shots is one that results in terrible malformations of the soul.” -James Hollis

Caring for the soul demands that you look at the inner effects of the decisions you’re making, not just the external cost-benefit analysis.

With each decision I mentioned, I asked myself the same question: Who will I become?

“Who will I become if I stay in Montenegro for the next 6 years?”

“Who will I become if I take the risk and leave?”

I saw I would become a resentful person if I kept living like a prisoner in my own home. As rich as my inner life was during those 2 years I spent mostly in my room, my life had outwardly stopped.

Visits from a couple of true friends and interactions with colleagues reminded me that life kept moving outside my walls. But my life was stagnant. I wanted to live. I wanted to love life.

I understand that some people might read this and think it’s easy to focus on your soul while making life decisions when you don’t have a family to support. And that’s a valid argument. It’s true that the fewer obligations and attachments you have, the more risks you can take in life. But that wasn’t my case.

My family was the reason why I didn’t leave Montenegro sooner. I wrote before about how being a pillar of support for my nephews gave meaning to my life.

The real question was, “Who will I become for my family, most importantly my nephews, if I stay in Montenegro and keep living like this?”

Do I want to be an uncle who is there and can buy them anything they want but hates life? Do I want these two boys, who already have so many unavoidable challenges lined up for them, to have me as living proof that life can turn people resentful and bitter? *And all of this with the assumption I would stay alive.

Or do I want to be an uncle who is away most of the time, cannot help them financially until he finds a way to stand on his own two feet (which could take years), but loves life and is able to encourage them in the face of any challenge they face?

I won’t say that the “correct” choice is clear. I’m not asking you to support the choice I made. But I’m telling you how I made it. Love for life and care for the soul took priority over everything.

When I decided to leave, I told my mother, “I want to be the living proof that you can create your life out of any circumstances and love it. Because they will need it.”

Regardless of my commitment to my family, I know this isn't the same as a father or mother who are reading this and cannot leave everything behind to start a new life. But, as I said at the beginning, it’s about the patterns of the story, not the exact decisions I’ve made.

No matter how many constraints there are in your life, you still owe it to yourself to ask, “Who will I become if I make this decision? What kind of person will I develop or degenerate into?”

Now, I want to introduce another idea that’s been helping me make life-changing decisions, especially since I decided to leave my home. Death.

“Though the physicality of death destroys us, the idea of death may save us.” - Irvin D. Yalom

Once it was clear I was leaving Montenegro and, with it, my job, it was time to figure out where and how to restart my life.

At that point, it had already been clear for a long time that I wouldn’t be able to continue working my air traffic controller (ATC) job anywhere else. The countries hiring foreigners wanted controllers with experience in bigger airports than where I worked. This left me with two options. Or, actually, it left me with one poor option and one insane idea.

The only thing where I had skill, competence, and credentials outside of ATC was physical training. In 2020, I started considering it as a backup plan since I had years of experience, (self)education and a PT license.

Fast forward to November 2021. After around one hundred applications sent for fitness industry jobs worldwide, I had one concrete option. I could go to UAE to start working on the gym floor as an instructor. The pay would be just enough to pay the bills, but there’s potential to work my way up to becoming a successful PT. Not the most attractive option, but a concrete and secure one. Amid my life's chaos, this would provide some well-needed stability and predictability. However, there’s a catch.

The schedule presented to me showed clearly that my passion project, the Recovering Overthinker, couldn't be sustained. If I were to fully dedicate myself to advancing in the highly competitive fitness industry, I couldn't spend nearly as much time on my writing as I have been up to that point.

The second option, or the insane idea, was to go somewhere far away and cheap enough to buy myself some time to figure out this online stuff.

At that point, I’ve been writing online every day for 1 year and 11 months already. I never tried to monetize my writing in any way. I couldn't wrap my head around the concept of making a living with my writing. But I saw there were people who cared about what I had to say, and they seemed to trust me. "Maybe I can figure this out. Maybe I can start making money from my online presence in a non-sleezy way." - That was the whole idea.

But what does death have to do with all of this? Well, "maybe I can figure it out" isn't exactly a strong argument to make a life-changing decision.

Death helped me decide. However, my unusual situation wasn't the only thing reminding me daily of how unpredictable life is and that it can end at any moment.

Before existential psychologists like Rollo May and Irvin Yalom pointed out the benefit of confronting our mortality, ancient philosophers, most notably Stoics, spoke about the same thing.

“Let us prepare our minds as if we’d come to the very end of life. Let us postpone nothing. Let us balance life’s books each day. … The one who puts the finishing touches on their life each day is never short of time.” -Seneca

“You could leave life right now. Let that determine what you do and say and think.” Marcus Aurelius

Inspired by the Stoics, I adopted the practice of Memento Mori meditation - a daily reminder of my mortality for the purpose of remembering to live. The idea of documenting my experience with this practice is one of the things that finally pushed me to create the Recovering Overthinker and start writing online.

But back to the story. The idea of death, both in the form of structured reflection and life's unwanted reminders, helped me understand what I had to choose to stay true to myself.

The idea of death fleshes out the reality of your unique life.

If I don’t know how much time I have left, I must honor what is in me - I must honor my soul - while I’m still here.

The only way to honor my soul was to keep writing. In retrospect, if I hadn't kept writing, I would’ve taken my life in 2022. You’ll understand that better through upcoming essays.

But how did I know what was in me? How did I know what I was supposed to do to honor it?

Let’s finally make this more concrete and practical because you all want that. (Thank you for sticking around up until this point).

I had that level of self-awareness because I would meditate on my death and think about what my regrets would be if I knew I was about to die.

“If I knew my end is near, what would I regret not doing, or not doing more of, not fully giving myself to?”

“If I knew my end is near, what would I regret doing too much, caring too much about, spending too much of myself on?”

For me, the answer was clear: expressing myself. Besides my loved ones, the thing that gave me the most joy in life was expressing myself through writing.

While allowing myself to feel the discomfort of imagining my dying moments, it was clear to me I would regret not giving all of myself to writing. I would regret not spending myself on the mission of touching other humans with my words.

It was equally clear I would regret caring about “how well I’ve done for myself” and how my material success compares to my friends and acquaintances. I would regret spending myself trying to make up for the money and social status I lost by quitting my job.

If I was about to die, the only thing that would matter would be if I honored what was in me.

When you find something that touches your soul, you must hold on to it for dear life. It just so happened that, in the situation that I was in, holding on to writing required me to make a living from it. That’s why I said don’t focus too much on my specific decisions and steps. Recognize the main pattern - that you must honor your life and soul before it’s too late. Because if you don’t, you will punish yourself from the inside, or rather, your psyche will punish you. You will suffer psychologically and spiritually if you betray what is in you.

So this is how I made the most important decisions of my life. This is how I decided to buy myself time and try to figure this writing thing out. It took way more than I expected, and I’m still figuring it out in many ways.

But I can wake up and know that my main task is to write. I can wake up and write!

Thank you for helping me. By reading what I write, you make my life choices seem a bit less crazy.

Friends, let me leave you with this. If it’s not obvious, making these decisions was terrifying. But for the first time in my life, I felt fully alive. And that’s the feeling I want for you.

Next time, I’ll tell you how an older Australian gentleman shattered my romanticized view of the adventurous life—one of the most sobering lessons of my journey. An important lesson, especially in our Instagram age where everyone seems to be traveling around the world. And crucial in the context of my story, where you might be tempted to think that the traveling is the coolest part.

Until next time.

1. I have to mention that, a couple of months after I declined the promotion, a gentleman from the very top of the company proposed that I be given a temporary contract without the restrictions that caused me to decline the promotion in the first place. The increased pay during that period before leaving Montenegro gave me much-needed time to find my way in the world. I'm forever indebted to that man.