Playing it safe is a slow and painful death (how to not regret your life)

In 2024 I quit my six-figure corporate job. Then I put my home in Chicago up for sale, and I left the United States to start a completely new life for myself in Portugal.

I did this because deep down inside I knew that I was getting too comfortable with life, and if I stayed in my comfort zone, then I would eventually live to regret never stepping out on a limb to create a life that I truly want for myself.

"The comfort zone is where things are predictable, secure, and easy, but it is also where growth comes to a halt. The real adventure of life begins when you move beyond the boundaries of what is familiar, when you embrace the unknown and face the challenges that come with it.” – Neale Donald Walsch

If you feel like you are limiting your potential in life because you hesitate to take risks or you’re afraid of the consequences of going against societal expectations, then keep reading because in this article I’m going to give you a strategy for breaking out of the self-limiting habit of always playing it safe.

And if you successfully implement this strategy, then you will become one of the few people who understands what it feels like to truly live life on your own terms rather than merely existing.

Let me start off with explaining my thought process for giving up almost everything, my job, my home, my comfort zone, and deciding to step into the unknown.  Then I’ll close out by showing you how to overcome any fears that are holding you back from experiencing life as you wish it to be.

By the conventional success metrics, I was in a really good place in life.

I had a relatively low stress six-figure job, I had a nice home in a good neighborhood, and I had a very stable and predictable lifestyle.

But that was the problem.  I was too comfortable.

You might think that having a comfortable life is a good thing, but comfort is a form of instant gratification, and too much of it is detrimental because it represents a state of stagnation.  Growth cannot happen in the shadow of comfort because comfort breeds complacency.

“Embrace the discomfort, because that’s where you begin to truly live." – Neale Donald Walsch

"Comfort is a drug. The more you get, the more you need. The more you get, the less you grow." — Michael Easter

I noticed that the more access I had to conveniences that made life super comfortable, the harder it became to let go of those things, and I started living in fear of losing what I spent most of my adulthood working to acquire.

This is what I refer to as the comfort trap, because the short-term gratifications of being comfortable is highly addictive. It’s very difficult to go back to having fewer things, having less money, having less identity-affirming status symbols.

These things for sure make life comfortable and enjoyable, but they do not bring the deep fulfillment that is missing in so many people’s lives.

So, what most people do is they give up on pursuing a more purposeful life that brings lasting joy and fulfilment because doing so requires them to face their fear of potentially losing what they’ve worked so hard to build. Instead, they settle for a life that’s “good enough”, but in the long run leads to regret for taking the path of least resistance.

I was on that comfortable path that leads to regret, and fear of giving up my comfortable life prevented me from creating my best life.

Fear of financial loss prevented me from leaving my job and actively pursuing my ideal of full-time entrepreneurship.

Fear of losing the status symbols that fed my ego and cemented my identity prevented me from selling everything I own and moving away from the U.S. to live a simpler and more connected life.

All of these fears influenced me to play it safe.  I played not to lose rather than playing to win. 

I fell into the comfort trap where I was complacent with a life that was “good enough.”

But as I got older and the prospects of my own mortality became more real, I had to ask myself the question, “if I’m not actively pursuing my higher calling in life, then what am I doing?”

It became apparent to me that I will eventually look back at the collection of experiences that make up my life, and I’ll realize that most of what I feared losing didn’t even matter in the grand scheme of things.

I would realize that playing it safe left me with a mountain of regrets for putting so much energy into holding onto the trivial comforts of life that won’t even matter in the end.  I’ll regret not giving myself an honest 100% effort to experience the full spectrum of life, both good and bad.

So I made the decision to give up the safety of my comfort zone, and start living a life that is way more in alignment with my ideals and my purpose.  I made a decision to start living authentically, whether it brings success or misfortune, because in either case I know that I’m not letting my fears prevent me from knowing what it means to truly live.

After I stopped playing it safe and started to experience the fullness of life, I took some time to observe others around me, friends, colleagues, clients, etc. and I now see that almost everybody is stuck so far down in the comfort trap that, unless they move with extreme urgency, they’ll forever be relegated to a life that’s “good enough” but never truly fulfilling.

This is how people end up complaining about being passed up for a promotion, feeling burned out by their jobs, or only getting a 2% annual pay bump that doesn’t even keep up with inflation, yet they stay in their jobs for years because the prospect of losing the salary, and the lifestyle that it affords is just too uncomfortable to bare.

I can’t speak for everyone because different people do have different ideals. However, I know that there are enough people out there who are experiencing life as an endless cycle of disappointment, resentment, and regret.

And living life in this way, in my opinion at least, is a slow and painful death that plays out over a lifetime.

"Twenty years from now you will be more disappointed by the things you didn’t do than by the things you did. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover." – H. Jackson Brown Jr.

If you want to stop playing it safe, and start living in such a way that when you are approaching the end of life, you look back and have no regrets, you must become fearless.

And when I say “fearless” I don’t mean that you must be free of fear. Fear is a necessary human emotion.  What I mean is that “fear” cannot continue to be the driving force behind your decisions in life.

You must have the ability to override your fear of loss, of rejection, of failure, of disapproval or anything else that comes with you stepping outside of your comfort zone.

Once you overcome your fears, you’ll be able to live fully so that you’ll have no regrets.  So, I’m going to walk you through a simple process you can use to overcome your own self-limiting fears to finally stop settling for “good enough” and start fully living.

Before I walk you through this framework, you may also be interested in knowing that I’ve created a set of A.I. prompts that fully automate the process in a structured and personalized format.  You literally just copy the prompt and paste it into either ChatGPT or into Cerebrum-X, which is the tool that I’ve created specifically for people who want to be more intentional about their lives, and it will guide you through the process so you can save your mental energy on actually implementing the strategy that’s provided here.

So if you’re interested in having access to my full database of A.I. prompts, along with the ones specific for this framework, then just click here.

With that said, the first step to stop playing safe, overcoming your fears, and living with no regrets is to…

Set the vision for your ideal life

Your vision provides direction. It’s your north star, and as long as everything that you do in life is aligned with your north star, then you can rest assure that you’re on the right track.

I know this sounds cliché, but it is really important because from my observation, most people don’t even get this first step right.  I have seen a stat floating around that 75% of Americans lack having a clear sense of direction, and if that’s anything close to being accurate then it’s a pretty good sign of how little time people actually take to live purposeful and intentional lives.

Your vision doesn’t need to be 100% accurate. You don’t have to know exactly what you want, but you do need to be directionally correct so that you can begin living and not just existing.

And as you navigate through life, your circumstances change. Your needs change. And so your vision will evolve, and you can make course corrections throughout.

Nonetheless, every decision that you make moving forward should align with your vision. This is literally the most basic requirement in making sure that you live a life that is true to yourself and free of regrets.

When the time comes for you to not take the safe or comfortable path, it’s your vision that’s going to keep you on the right trajectory when you inevitably face the temptation of staying in your comfort zone and settling for “good enough” instead of great.

Some of you may already be super clear about your vision, but if you do need a bit of help, then you can use the prompt that I mentioned earlier and it’ll guide you through a series of journaling questions to help you to define your vision. Along with your vision it’ll also present a suggested purpose statement based on your journaling, which is super helpful because your purpose is actually the inspiration behind your vision.

And once you do this, next you’ll need to …

Discover the fears that are causing you to play life too safe

Now that you have a clear vision you need to take an honest inventory of your life as it stands today, contrast it with your version of a full and ideal life, and then figure out what’s standing in between your current and ideal life.

It’s this space in between your current reality and your ideal destination that holds the clues to where you might be taking the safe path.

So at this point you need to literally write down what life is currently like for you, then write down your dream life in the form of the most perfect day imaginable.

Then you identify the specific actions you would need to take to turn your dream life into a reality.

Once you do this, you can do a bit of introspection by being very honest with yourself about why you’re not currently taking those actions. You need to dig deep, figure out the fears that are preventing you from doing what you need to do to stop passively existing and to start actively living on your own terms.

Basically, what are the discomforts you will experience for taking massive action towards your dream life and why do you fear facing these discomforts? 

For example, if you want to leave your 9-5 career in pursuit of entrepreneurship and more time-freedom, do you expect to face financial uncertainty that requires you to downsize your life? Will you risk your reputation and the possibility for future opportunities? Will you need to give up the high-status lifestyle that feeds into your identity? 

If you want to let go of toxic people that drain your energy, and start enjoying healthier relationships that elevate your life, do you expect to experience some conflict? Will you face disapproval from others who want you to stay on their level? Will you have to spend more of your time in solitude as you become more selective about who you share your energy with?

These are the self-limiting fears that, if you don’t address head on, will keep you in the safety zone. 

Your self-limiting fears are causing you to stay in your soul crushing job, or in that toxic relationship. They are leading you down a path of regret and resentment when you are older.  They are causing you to live out your life as a slow and painful death under the promise of staying comfortable.

It is super important that you commit time and energy into really understanding where you are hesitating to take action in your life based on fear, because if you’re focused on the wrong things, then you’re not going to produce the actual life that you want.  And that defeats the purpose of doing all of this.

So pay close attention to the actions that bridge the gap between your current life and your ideal life, and make an honest effort to understand exactly why you’re either not taking action, or why you’re acting with a half-hearted effort, or why you may have tried in the past but quit as soon as you faced a bit of adversity or uncertainty.

The more clarity  you can get around this, the better.

I strongly recommend creating a list of self-limiting fears, then writing down the actions that’ll align you with your ideal life along with your reasons for not taking those actions up till now.

If you use the A.I. prompts that I created specifically for this framework, then this part will happen automatically for you, so you’ll have all of this information saved and organized so you can come back to it instead of forgetting about it, which tends to happen with these kinds of exercises.

Now that you’ve identified your self-limiting fears, you’ll need to work on overcoming them, and I’ve found that one of the simplest and most effective ways to do this is by…

Answering the question, “realistically, what’s the worst that can happen?”

When you think about the downside potential of grand life decisions, you, like many other people, probably assume catastrophic consequences that will essentially ruin your life forever.

However this is an unrealistic take.

The reality is that if you are someone who has made it this far in life, then you have knowledge, and skills and adaptability to manage your downside risk.

Stepping out of your comfort zone, is uncomfortable, but if you manage it properly it you can operate in a controlled discomfort rather than in chaos.

Take for example the downside of quitting your job and going into solo entrepreneurship like I did.  The most obvious risk is that you’ll no longer generate reliable income (at least for an undefined period of time).  However, this does not mean that you will be on a path to immediate financial ruin.

There are steps you can take to mitigate and manage these risks.  I won’t list them all because they’re quite specific to each person and scenario, but in the case of no longer receiving income, one has several options, including but not limited to:

• Saving up a cash cushion before hand

• Drastically minimizing spending on unnecessary things

• Moving to a lower cost of living geography to reduce burn rate

• Finding temporary job opportunities in the event that a cash influx is needed

So when you ask yourself “what’s the worst that can possibly happen?” you should consider the reality of your life circumstance, your skills, as well as your ability to navigate and adapt to changing tides. When you factor everything into the equation, you may find that the worst case scenario is really not that bad.  Yes it’ll exist outside of your comfort zone, but it’s not anything that you can’t actively manage.

Then you should envision all of the different worst-case scenarios that you can possibly think of and come up with a response plan for each.  This helps to allay any fears you have by adding a degree of certainty and confidence that was missing before.

When you do this, you have no justifiable reason anymore to continue playing it safe.  You’ve dissected the downside risk, and set up a plan to manage those risks. 

I wish I could convey to you the psychological boost you will experience simply by doing a mental walkthrough of each worst-case scenario. Doing so dramatically reduces the perception of risk for any of those big life-changing actions identified in the previous step.

In my experience, doing this really makes me realize how much I allow irrational thoughts and fears hold me back from living a life that I can look back on with no regrets.

Now, just like the previous two steps, you need to write down, and make a literal list of, your worst case scenarios and your prevention/mitigation plans so that you can revisit them in the case you need to actually use them. 

Again, the prompt that I mentioned earlier in this article will automatically walk you through this process if you wish to use it.

And now that you’ve come up with a plan for overcoming your self-limiting fears so that you can really start living and not just existing, there’s one last piece that’ll be super helpful, which is to…

Train discomfort like it’s a muscle

At this point, you are ready to take things to the next level by training yourself to become comfortable with being uncomfortable.

I know this sounds like a bit of a cliché, but learning how to embrace discomfort is where the magic happens.

In my experience of leaving my job, moving to a new country, and starting a solo entrepreneurship endeavor, the single biggest difference maker in my life has been having a default setting that favors discomfort.

I noticed that where most people hesitate in life, I just take action, and I think it’s because I have intentionally practiced various forms of voluntary discomfort throughout my life.  So I’m somewhat desensitized to discomfort.  For those common areas in life where people are compelled to play it safe, I just don’t experience enough fear to prevent me from taking action to bridge the gap between where I currently am and where I want to be.

And you can do the same by programming both your subconscious and your rational mind to also be desensitized to fear. 

You do this through voluntary discomfort which is the practice of intentionally subjecting yourself to uncomfortable situations, and conditioning the mind and the body to be fully present and non-reactive in the face of said discomfort.

“The more you callous your mind, the stronger you become.” – David Goggins

"The only way to become calloused mentally is to do things that are uncomfortable. You have to choose to endure the pain." — David Goggins

There are lots of different ways one can practice voluntary discomfort.  One of the most common is cold plunges which I am a big fan of.  However, you’ll want to be a bit more targeted with how you go about doing this.

You’ve already identified core actions that you need to take to bridge the gap between your current and ideal life. You’ve also spelled out the fears which are holding you back from taking action along with the reason behind your fears.  So now you’ll want to adopt a voluntary discomfort practice that’s specifically oriented towards the fears that you need to overcome to turn your ideal life into a reality.

So if fear of financial insecurity is the limiting factor for you, then adopting a voluntary discomfort practice where you spend one week every month simulating frugal living conditions could be something worth exploring.

For one week you could live on an extremely small budget, take the bus around town, unplug your TV, lock away all of your “expensive” toys, and avoid streaming services as if you’ve discontinued your subscriptions.  This is just an option that I’m thinking of on the fly, but I think you get where I’m going with this.

When you do this, you build confidence in your ability to survive and maybe even thrive, despite being in a scenario that you fear.  When you get small doses of exposure to things that you fear, you start to build up a sort of immunity, or desensitization, to those things.  You start to realize that life goes on in spite of your fears playing out.

So this is the icing on the cake, so to speak.  You’ve already done the work to minimize your self-limiting fears, and here you’re building confidence in your ability to endure.

So create a list of voluntary discomfort exercises that you can practice to directly confront your self-limiting fears head on, and this will give you that final push that you need to send you over the top.

And once again, the prompts that I mentioned earlier in this article will guide you through this process and recommend a number of voluntary discomfort practices you can incorporate into your routine.

If you follow this process then you’ll for sure experience the mindset shift that you need to finally stop living on safety mode and start taking risks. You’ll find it much easier to live on the edge of your comfort zone, and I’m confident that you’ll find far more fulfillment and life satisfaction there than you would if you decided to always live the comfortable life.

I believe it was Ben Franklin who said that most men die at 25 but are buried at 75.  I take this to mean that people experience a sort of death of the soul once they enter adulthood, because they give up on creating a life they truly want for themselves and end up falling into the comfort trap where they relinquish their highest potential in exchange for trivial comforts that numb them to the full experience of a life well lived.