The Real Life Office Conversation That Changed My Life Forever

Note: These are paid actors. Not the actual office I worked at.

I’m sitting across a table in the office of my CEO. My heart is beating a million beats per minute wondering why I’m even here. Am I being promoted? Am I in trouble? Did I ding his car in the parking lot this morning?

After I sat there for what felt like the most excruciating 10 seconds of my life, he rolled his computer chair over to the table and got right to the point.

CEO: “You know what your problem is. You’re arrogant, and you assume everyone else is incompetent.”

The rest of the conversation was a blur as it felt like I’d just been emotionally punched in the face. I think I kind of went into an out of body state as I only vaguely remember being berated for the next 15 minutes on the topic of my arrogance and how little I knew about anything design related. But the exact words of that opening line have stayed with me for over 8 years.

In terms of most fear-inducing work conversions, I think that conversation is second only to the time a coworker/pseudo-manager at another company threatened to kill me for something I had said to our mutual boss that he thought made him look bad.

As I walked out of that office, I felt such a cocktail of emotions… fear, anger, despair. I wasn’t being fired, but I knew I had stepped on a company landmine that would forever alter my career path.

So one might ask, what precipitated getting such a verbal beatdown from the CEO of the company you work for?

One email.


The company I was working for then was venturing into an industry they had never worked in before (web design/development) and I had been instructed that I would be working on this unique project. At the time, my job there was mostly server testing, but I had worked in web development all the way through high school and college and I loved it. The company owners knew that because the way I had gotten my start in computer testing was developing and running a website called Excessive Hardware, a computer hardware news and reviews website. They were also aware of this because as a testing intern I voluntarily rewrote their website in modern HTML/CSS in my spare time while I was waiting for tests to finish. At that point, the website had been created and was being updated with Microsoft Frontpage, and the old code that tool was generating was frequently having browser compatibility issues as newer browsers like Chrome/Firefox were coming into the foray and slowly overtaking Internet Explorer.

So now that I recall the first web development run-in at that company, maybe I should have seen the landmine I stepped in that day coming. My recollection now of that first web project was that when I sent the rewritten version of the website to the company owners, they seemed more concerned about how I had so much free time to be able to have written all that code. They never used the rewritten website for reasons that I won’t get into here (hint: It had nothing to do with improving the quality of the website). And for the record, the way I had so much free time was that as a tester, there are hours and hours of waiting for tests to finish and most of the staff would just surf the web during those hours. It’s an unspoken perk of being a tester: Yes. You might “work” an enormous amount of hours, but you get to spend a lot of that time doing whatever you want as a long as you looked busy on a computer.

The Email

Before I wrote this infamous email, I had just been sent the mockups from the graphic designer of what this new website was going to look like and it would be my job to turn those designs into HTML/CSS. Honestly, as soon as I saw these mockups, I was disgusted. I thought it was one of the ugliest looking websites I had ever seen (it still ranks up there). I shared it with a few graphic designers I had worked with on freelance websites in the past, and there was universal agreement that it was just patently ugly so I felt like my opinion wasn’t unfounded.

This new website was a pet project for the CEO of the company because he had an existing business relationship with this client. So I sent him an email that said something along the lines of “I’ve been freelancing in web development for a while now and developed a number of websites over the years, and this design just isn’t very good. [INSERT COMPANY DESIGNER] isn’t experienced in web design/user experience.” (He wasn’t. He had mostly been making graphics for reports) “I think we should hire someone who has experience in web design to do the mockups for this website since we haven’t done a lot of other web projects and want it to look as good as possible.”

Silly me thought, “This is the CEO’s pet project. Obviously, he’ll agree with me wholeheartedly and thank me for my feedback because we all want this site to be as beautiful as possible.”

Nope. The next words I heard from him about this project were “You know what your problem is. You’re arrogant, and you assume everyone else is incompetent.”

Lessons learned from a sucker-punch

That day and that conversation was a very formative moment in my life. I’ve learned a lot by thinking on that experience over the years. Long term, I think it sent my brain into the mode similar to when a child puts his hand on a hot stove of, “Wow. That really hurt. How can I prevent that from ever happening again?”

One answer to that question would be to just keep my head down and never again question the quality of someone else’s work. That’d be the safest thing. And that’s what I was being told to me by the CEO: Don’t swim out of your lane. Just write the code you’re told to write.

The problem for me wasn’t so much the true quality of the work I was questioning (design aesthetics can be very subjective). The issue was realizing that even questioning the quality of someone else’s work could subject me to such derision from the highest levels of leadership at the company. And I didn’t want to have to compromise my personal principle of trying to produce the best work possible to maintain the principles I was being told by the company’s CEO of “Just do your job. Don’t question others.” So my answer was to start asking “How can I work in an environment with the independence to try to create the best finished product without fear of being attacked for it?”

And that question started me down the path of getting serious about how I could change my life to give me the space to produce the best work possible.

The risk of just one job

One thing I quickly realized from that incident, is that when you’re working for just one company, you have so much financial risk at stake with losing that one job that you’re not really in a safe position to truly be honest when you think the company isn’t producing the best work. You might gripe to your coworkers about it, but talking to anyone above you could get you canned. This is especially true at small companies where your boss might be the CEO/owner so they can essentially fire you whenever they want, for whatever reason.

And the price of your honesty could be that your income will go from $4,500/mo to $0/mo. I didn’t have any kids, but at the time my then-wife was a full-time student in university, and she had a lot of health conditions that required insurance, so I felt an obligation to provide for her and make sure she was taken care of and I knew that COBRA insurance after you get fired is ridiculously expensive. That obligation wasn’t something I begrudged. It was a commitment I had made that I needed to take into consideration for any decision I made.

I know the way a lot of people achieve the freedom I’m describing is by saving enough “f — you money” (a.k.a. an emergency fund) that if they ever get fired or quit they’ll have plenty of money to live on until they can find a new job. Having savings to allow for that is a good idea, but at the time I didn’t have much savings because I had only recently graduated from college and was supporting someone else, so it was a very gradual process to build up those savings at the time. I also didn’t like the thought of the instability of going from job to job. Not only does it look bad on a resume and is pretty stressful, but when your employer is providing all kinds of benefits like health insurance, 401k, and disability insurance, it’s a major hassle to have to start at new companies and fill out mountains of paperwork to change all that over every time.

So rather than being so reliant on a single job from a single company I decided I wanted to start doing lots of little jobs for lots of different companies. In financial terms, I wanted to “diversify my portfolio” of jobs so that if anything happened to my working relationship with any one of those companies, I would still be okay financially.

How to get there and stay there

But don’t read this and quit your day job today to start freelancing. Then you go from 1 income source to 0 income sources. That’s the *wrong* direction. Fortunately, most full-time jobs are only 40 hours/week, so that leaves a lot of extra time to start adding on these small jobs. Every single job you get makes you slightly less reliant on all the other jobs.

Your end goal is to never have a single job that’s “too big to lose.” I’ve turned down huge projects because I felt like it put me at too much risk of being dependent on a single client. The bigger a client you take on, the bigger risk you have of compromising your principles.

And I think one way a lot of freelancers get themselves into trouble down the road is that they see the allure of landing a big job with a big new client and they just drop all their other small clients to dedicate their time solely to the big client. They may also inflate their lifestyle because of the income from this single client. Once you do this, that company is no longer a client, they’re an employer. And you’re no longer a freelancer. You’re just a contractor that this company can fire at any time without even having to pay unemployment benefits.

How this works in practice

I had a situation recently where one of my biggest clients was pushing on me to make some exceptions that I wasn’t making for any other clients. And while I did make a few accommodations for them because I value them as a client and want to maintain the best working relationship possible, I still had to draw the line in a number of ways to maintain my principles. And if I wasn’t in a position to lose them as a client without majorly affecting the business or my lifestyle, I don’t know if I’d be able to draw that line. In the end too, I think they appreciated the things I pushed back on.

Another advantage of working for lots of companies is that for every single company/person you do great work for, you have a potential new referral source. Sometimes even big referrals can come from small clients. There’s a great network affect. But when you’re just working for one company at a time, your potential new referral sources are very limited. And my experience is that those bigger clients are a lot less likely to refer you too because often big companies have legal requirements preventing them from referring you and there can sometimes be the sense of “This is our guy. We don’t want to lose him to another company.” It becomes more like when you have a full-time job and your boss gets a call to be a reference on a new job you’ve applied for.

There are struggles as well that come from working for lots of people, but in my experience, the advantages far outweigh the disadvantages of truly having the independence and freedom to do the best work you can, uninhibited.

I want to put a disclaimer in here that the instance described above with that CEO is only a snapshot in time from many years ago. People can change and company culture can change. Had I sent that email today, it’s very possible I wouldn’t have gotten the same kind of response as I did back then. The purpose of telling the story of this event isn’t to disparage that company, or it’s CEO, but to tell others what I learned from that event and how it changed the direction of my career and my life.




eCommerce Web Developer (Magento/Shopify). Remote Worker (currently working from Miami Beach). Business Owner ( Cat Lover (Cookie/Fender).

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Mark William Lewis

Mark William Lewis

eCommerce Web Developer (Magento/Shopify). Remote Worker (currently working from Miami Beach). Business Owner ( Cat Lover (Cookie/Fender).

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