In the last post, I gave you the cheat sheet on How to be Extraordinarily Ordinary. I wrote that post largely due to my own personal experiences and observations. It represents a path I have so desperately sought to avoid, and so desperately want you to avoid: mediocrity.

Today, I offer the first step of the antidote.

  • If you’re dreaming about leaving the job you hate but can’t quite imagine a scenario in which you’d actually take the leap, here’s the first chapter of your playbook.
  • If you’ve ever gazed out from the window of your office, wondering what it’s like to really experience all that life has to offer, here’s section one of your manual on how to do it.
  • If you’re scared to approach your boss about leaving your job due to any number of irrational fears, here’s unit one of your guidebook on what to expect.
  • If you desperately want to find meaningful work, I have the blueprint for you. I’m living the blueprint as we speak. I’ll show you the promise and the pitfalls, the risks and the rewards. But it all has to start with one decision.

Today, I offer you a window inside the day that I made that decision to say no to mediocrity. It was the day I took a huge personal risk that changed my life forever, and opened me up to a world of adventure, opportunity, serendipity, and exploration.

The following conversation is paraphrased for brevity and anonymized for obvious reasons. The bracketed numbers correspond to the lessons outlined below.

Friday, September 8th, 2016 – 3:30pm

I walk into my boss’ office to break the news that I will be leaving the payroll company and the cubicle in which I spent 40+ hours a week for three years.

Boss: Hey Joe, what’s up?

Me: Hey, I just wanted to let you know that I’m planning on leaving this job. But I’ll stay until W2 and year-end tax season is finished. I just wanted to let you know ahead of time so that you can train a replacement. [#1] [#2] [#3]

Boss: Oh. Okay. What do you plan on doing instead?

Me: In all honesty, I have been feeling limited and underutilized in this job. I don’t have a plan at the moment, but having some time to travel and explore my options is what I really need at this point in my life. I’m in my mid-20s, and I need to take advantage of this time to figure out what I really want. [#4]

Boss: I just don’t understand. I gave you this position (tax specialist), I have paid you well and given you raises. You have health insurance and two weeks of vacation. Why would you leave for such uncertainty? [#5]

Me: I sincerely thank you for everything you have done for me. I’m sorry, I just don’t think this job is for me, long term. I know there is much more in this world for me to learn and do, and none of that can be done while I work full-time here. [again, #1]

Boss: Do you know how many people I’ve turned down for a job here? [#6]

Me: I don’t know how relevant that is to my situation, but I understand that there are plenty more people out there who would love to have this job that I’m leaving behind.

Boss: Are you sure you are thinking straight? Are you sure your mind is in the right place? You don’t suffer from any mental condition? [#7]

(At this point, if there was a 0.001% chance of me staying, it quickly went to zero for this exact reason.)

Me: No, really, I feel that if I commit to a job I dislike, I’d be doing both of us a disservice. [#8]

Boss: Look, I built this company out of necessity. I don’t even like the work I do. [#9!] But as long as companies are paying their employees, we will be in business and we will be making money. If you don’t want to be a part of that, I can’t stop you. But I appreciate your consideration in letting me know so early.


Let me be clear, my former boss is a good guy and he did a lot for me during my time with the payroll company. But this conversation served two functions for me. A) it was the spark I needed to never commit to a life of mediocrity, and B) outlined the mentality of people who have committed to a life of mediocrity.

Let’s take a look at the primary lessons from this conversation. Numbers 1 through 9 correspond to segments of the conversation, and the rest are overarching, big picture lessons.

  1. Never burn bridges. Make sure to be as respectful and considerate as possible while cutting the tethers. You never know if or when you will ever cross paths with your boss again. You never know what opportunities or in what capacity you may need to call upon them in the future.
  2. You have decided that you value your time, abilities, and untapped potential more than your boss does. Be as clear and direct with them as possible. Leave no room for confusion. You have no tolerance for mediocrity. You are taking control of your life, and no one should be able to talk you out of it.
  3. Sooner or later, you need to realize that you are replaceable. If they can train you to do the job you do, they can easily train someone else to do your job for cheaper. That day will come. And with each passing day, it will come sooner than you might imagine.
  4. If you’re thinking of one day quitting your miserable job, please don’t do it before you have a plan, unless you have the time, resources, and freedom to take such a risk. (But also guard against using prudence as an excuse for not taking action).
  5. Your boss will most likely be taken aback, especially if you’ve been a reliable employee for 3+ years. Level one of their defense will be summarizing what they have done for you. Listen closely–they will show you their exact repertoire of tools most companies use to keep employees firmly entrenched in a career of paper-shuffling. (Because why would anyone choose this kind of work?)
  6. Level two: they will use social proof. They will employ the “finish your food because there are hungry people out there” strategy that you might have heard from your parents during your childhood. Don’t let that fool you. You are replaceable.
  7. If all else fails, the boss will begin to question your sanity. As stunned as I was to be asked such a question, I recognized it for what it was: a get-out-of-jail-free card. There was no going back at that point, and this question helped me to never regret it.
  8. Keep a level head. Remove emotion from the equation. Stick to the truth. Understand what many bosses can’t: if an employee isn’t happy, it will negatively impact the operation of the business. Sometimes loyalty and dedication can’t be bought.
  9. This is one of the all-time memorable lines in the history of boss-employee interaction. Whenever meaningful work is on my mind (which is often), I can still hear him repeating “I don’t even like the work I do” in my head. At least he was honest! This is the clearest lesson to be careful about which path you take. Get too far down the wrong path, and you’ll spend all of your life either retracing your steps or hating the work you do.
  10. If you are going to set out on your own, keep an eye on your motives. If it is your dream of doing business deals, taking phone calls all the time, going on sales calls, managing employees, and the status symbol of being “boss” that motivates you, you might be condemning yourself to misery of a different flavor. On the other hand, if you are drawn to the values of creativity, helping others, and personal freedom, then you have a lifetime of purpose ahead of you.
  11. You will be tempted (in fact, we’ve all been programmed) to stay true to the safe course and take what is “guaranteed.” Refer to #5 again. The safe road is guaranteed income, healthcare, two weeks a year of vacation, and a guaranteed (and crowded) path to mediocrity and misery. The safe path is easy, which is why everyone takes it. If you want any sort of significance, adventure, meaning, or anything beyond the grey walls of your cubicle, you must be willing to make the hard decisions, do the hard things, and take full ownership of every aspect of your life.
  12. The promises of the future rarely ever turn out the way you envision. Banking on retiring to a sunbathed town in South Florida 30 years from now? Think you’ll be swimming in millions of dollars of your own hard-earned salaried work? (Here’s a surprise: when you get older and too expensive, refer to #3). Look at how much your life has been changed by COVID-19! Think these things won’t happen multiple times in the next 30 years? Anything can throw your carefully curated plan far off course. In these situations, would you rather put your destiny in someone else’s hands? Or would you rather have full say over your life and build your own path to freedom? Good news: It’s an easy answer. Bad news: it’s a hard decision.
  13. Speaking of surprises, we all love a Baker’s Dozen: If being self-employed is your objective, you will learn that running a business is NOTHING like what they teach you in business school. After I left the payroll company, I eventually went on to learn the ins and outs of business through managing a 80+ employee, multi-million dollar restaurant. Managing a multi-variate complex system like this gave me the knowledge that can be applied to anything I do for the rest of my life. Moral: don’t pay ridiculous sums of money on irrelevant business school classes. Find a way to learn on someone else’s dime, so you will be well positioned to pursue your own personal and financial freedom.

The Wolves or the Waterfall?

I envision most people’s careers to be a perpetual scenario where they are standing between the edge of a huge waterfall (financial and personal freedom), with no view of what’s below (inherent risk), and a pack of wolves (9-5 mediocrity, other people’s expectations) ready to tear them to shreds. You can test the waters all you want, but I doubt the water temperature will matter once the wolves get a hold of you.

Don’t get eaten by the wolves. Don’t live your life according to what the wolves will allow you to do. Don’t relegate yourself to a lifetime of meaningless work and mediocrity. It’s a risk almost guaranteed to fail. (At least if this scenario were real, the wolves won’t lead you on so much!)

Take life into your own hands and jump. If you position yourself to land properly, and you learn how to swim, you stand more of a chance of surviving than if you face the wolves. When you plunge into the water below, you will have a difficult journey to safety, but at least you’ll have the ability to swim your way to freedom.

Dare to Say No

While personal and financial freedom is the ultimate goal, it doesn’t just happen on its own. This post represents the spark that will send you off into deep exploration. It is not the stagnation in mediocrity, but the pursuit of purpose and meaning that will bring value to the lives of others, which will ultimately give you the freedom you so desire.

And that, in a nutshell represents what this blog is about. If I can convince just one person to take full control of their destiny, add value to at least one person’s life, challenge one person to live life at full potential,  encourage one person to live a truly unparalleled life, then I feel like I’ve done my part in moving the world forward. Because eventually, the world will move you forward whether you’re ready or not. So why not get a head start?

Say no, once and for all, to mediocrity.

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