Quitting My Day Job: The Top 24 Things I’m Not Going to Miss

So, I’ve done it. Gone for it. I’ve left the working world behind and I’m making a run at being an author full time, as of January 1, 2020. The fates have aligned, the clouds have parted, and I have an opportunity to do this so I’d be a fool not to do so.

It will be challenging. Hell, it may even be a downright slog and I could utterly fail. But at least I’m trying.

My day job has been at my own company for the last 22 years, and if you’ve ever been self-employed you know that the one rule of running a small company is that you are responsible for EVERYTHING. Getting work, overseeing work, doing hands-on work, doing work while you are supposedly on vacation, doing work when normal humans are sleeping, getting paid, chasing down late payments, hiring staff, paying staff, fringe benefits, taxes, legalities, office culture, office supplies, leases, cleaning crews, electricity, internet service, running water, making sure we have toilet paper, etc, etc, etc…

Plus, as a digital agency, we wouldn’t exist without our clients. Which meant that the clients ruled everything. That is its own special flavor of fun.

To be clear, I worked with A LOT of amazing people, both as clients and as colleagues. The company staff was routinely wonderful, which I am ever thankful for. If there had been office bickering and culture issues, I probably would have gone insane long ago. I enjoyed countless moments with the people around me.

This post is more about the job…

So, to remind myself of the things I won’t be missing about my 9-to-5 job (that was really more of a round-the-clock job), here are The Top 24 Things I’m Not Going to Miss About Working My Day Job:

1. Pitch Meetings

A lot of authors are introverted, so count me among them. I don’t like having to be “ON” in front of spectators, unless I choose it (me playing guitar in public is a totally different beast). However, in my agency job, it was a regular requirement for me to go out and pitch new clients, basically the industry equivalent of singing for your supper. Bad pitch = no job, no job = no money. I’ve done it multiple times in a day, on back-to-back days, for projects I could do in my sleep, for projects I had no idea how to do, and in all kinds of health, including feeling like I might keel over and die while talking. I managed to have success at these for 2+ decades, so I imagine I’ve done a decent job, but still, I have nightmares where I am in a pitch meeting.

2. Conference Calls

Similar to pitch meetings, but with the added benefit of happening weekly or every two weeks. My job was typically to run the conference calls, which meant I had to know everything that’s happening, and all the next steps – not just what happens tomorrow, but everything from A to Z, so that when clients come up with a question out of the blue, or they decide their COO has to be on the call one morning, I have answers. Again, I did it, and did it well, but it was always stressful. Plus, it’s a chunk of time out of your day you don’t get back. And don’t get me started on the clients who were ALWAYS late getting started and ALWAYS ran over time.

It was said on many occasions that conference calls were just therapy sessions – that the client would vent all kinds of bizarre and unrelated things going on in their organization on a call, just to have someone to hear them. So my job meant having to know all the details of a project, and be some people’s accidental therapist. Count that as another hat to wear.

3. Being On-Call 365/24/7

When you run the show, the show can run you back. In the early days of my agency, in the 1990s, connectivity was a lot harder. If I went on vacation to the Caribbean, let’s say, it was very likely that they had little to no Internet service. An Internet cafe was the best option, and all I had to do was avoid those and pray the folks back home had things under control. Thankfully, they usually did. But later, especially into the 2010s, everywhere I went there was service. This meant that I found myself working at 3am in Barcelona, Spain, while supposedly on vacation, so that my work would be done in time for folks waking up on the east coast of the US that morning. I already noted my dislike of conference calls; you can only imagine how much I disliked doing conference calls when I was in another country and my entire family was off having fun.

4. People Who Don’t Understand My Job Telling Me How to Do My Job

As the head of a digital agency, it was my job to be on top of the technology we used and recommended to our clients. That ended up being a pretty daunting proposition, as virtually every client used something different. (Admittedly, we made it a point of pride to have diverse clients, so we sort of brought this on ourselves.) Still, I put a lot of time and effort into knowing what I was talking about. I hated most the pitch meetings or conference calls when I felt even a little bit unprepared. So when I was certain I knew my stuff, it was infinitely frustrating to have someone come along and tell me how wrong I was. Often, this was a higher-up on the client end, and typically one with debatable technology skills. I knew I should sit back and let them make bad tech decisions, so that I could charge more to clean up the mess, but frankly, I don’t like cleaning up messes. Still, it happened all the time. And believe it or not, some of the worst offenders were people in technology positions who should know better: CTOs, programmers, third party vendors doing tech and development work, IT directors.

5. People Who Don’t Keep Track of What’s Happening With Their Own Project Needing an Update on Their Project

I mentioned conference calls, above. In general, those calls were status updates, and one of the more frustrating thing was that certain clients typically had no idea what their status was. Worse, they often had zero updates from their end. Trust me, any agency project requires collaboration between the agency and the client. If the client has NO UPDATES on their end, it is very likely the project is standing still. And that creates all kinds of hell at the agency.

Still, one of the more ridiculous moments I had on a conference call was a client who was LIVID about the status of their project. Furious that we were not getting things done in what they considered a timely fashion. I spent an hour explaining where things stood, and politely but firmly pointed out how the client was not providing information and content we needed to make progress. When I finally finished, waiting for a new batch of ire to be sent in my direction, I heard silence. After a moment, I did the old “hello, hello, are you there?” at which point the client un-muted themselves and admitted they had been distracted and weren’t listening. For the entire hour.

6. Waiting for a Payment/s

So the job itself isn’t stressful enough, eh? Okay, let’s add a wrinkle. As business owner, you also need to pay attention to organizational cashflow, and oh, by the way, 6 clients are 30 days or more late on payment. But your staff still gets paid every two weeks no matter what. Fantastic. Kill me.

7. Catastrophes As Soon As Not Convenient

Everything ALWAYS worked fine when I was sitting at my desk, rested and refreshed, and ready to take on the day. ALWAYS. But put me in a car going to an airport, or taking the afternoon off to attend a baseball game? BOOM! That’s when the shit always hit the fan. I remember vividly hiding in a back room at Nationals Park (a party room no one was currently using), on my phone tediously trying to debug server issues for 2 hours while the fans cheered outside. I remember vividly using a WiFi hacking antenna to sap remote strangers’ Internet service just to finally be able to get online to fix problems while out of town.

8. Angry Clients

Look, for the most part, the clients were easy to work with. But, just as in every day life, you meet some nice folks and some not so nice. An agency needs clients to make income. You don’t often get to choose based on whether they’re “nice” or not. So, if you started a project and one of your client contacts rubbed you the wrong way, well, buckle in, because they aren’t going away. And grumpy clients at the outset often turn into angry clients if anything at all goes wrong. In the course of a six-month or twelve-month project, SOMETHING is going to go wrong. That’s when you can either work together on a solution or start fighting. The angry clients always made this experience terrible, and made their project worse for it. Was it sometimes my fault? Of course. But we spent a lot of effort to be on the ball and conscientious, so the times it was “my fault” are fairly limited. Does that matter to a client who has decided to be angry? Nope.

9. No Boss? Try Dozens!

One of the things people always say to business owners is that it “must be great to have no boss.” That’s hilarious. Sure, there was no cigar-puffing J. Jonah Jameson yelling at you from his corner office while you toiled away, but here’s the thing: EVERY client is your boss. EVERY client can fire you. And that has serious implications… Had a crappy conference call with an angry client (who may or may not have paid attention and may or may not understand that they themselves are integral to the success or failure of their project) and they decide it’s time to fire your agency? That’s money, gone. Money gone might mean people gone. People gone might mean you can’t do the next job. It’s a delicate and stressful cycle, all controlled by your many client “bosses.”

10. Random Technology Changes

Technology is always evolving, for countless reasons. Code patches, new features, new functionality, security updates, yeah. But also mega corporations deciding to reinvent themselves with no real concern what that does to a smaller organization who already put a lot of time into a product and now has to do it all over again with no additional budget. Plus, clients in general have no concept what this means. Tell a client that you need money to update their app from iOS 10 to 13, and they turn around and ask you why you didn’t program it correctly. Why it wasn’t future proof and made to last. Will they understand that Apple deprecated an important method and now advises code be altered in specific ways that have widespread ramifications? Nah. It’s easier just to be mad.

11. Random Technology Failures

This is even more fun than random changes. What’s the one thing computers are supposed to be good at? Following rules. If you code something to produce XYZ today, it should produce XYZ tomorrow, the next day, and on until infinity, assuming the environment stays the same. And yet… Ever had your laptop freeze up for no apparent reason? Ever seen a glitch where there never was a glitch before? Yep. And it’s not even a joke that the go-to response from people in tech is always the simplest: if you can do so, reboot. Three times. Bad news, though. In production environments, that can be a very, very bad idea, and no client wants to hear that you lost data (sales, user records, whatever) because of some random occurrence. They will want to know what went wrong, and they will want a sacrifice for the trouble. That was me. Have you ever asked Microsoft for a sacrifice when MS Word crashed and you lost that doc you’d been working on for 3 hours? No. But if your web server randomly crashed one day, that was clearly my fault.

12. Hackers

Even worse that any random change or failure, hackers screw up things on purpose. In my opinion, hackers are the worst of the worst. And what’s even sillier is that we’ve had massive hacker issues based on mistaken identity – I remember one group of hackers attacking my client endlessly because of the acronym their organization used. It happened to be the same as another org in another country that the hackers didn’t like. Rather than find the right one, they hit my client, hard. It takes a lot of time and effort to thwart an attack, and even more to clean up after a successful attack. Ever tried to manually scan every file in a filesystem containing thousands? I’ve wasted so many hours of my life dealing with hacking. What would I do with that time back?

13. “I Quit”

While I did very much enjoy working with my colleagues, I can tell you as the person running the show that someone quitting always hit hard. For the most part, people didn’t quit in anger, but for more money, a change of scenery, or an opportunity more in line with what they wanted to do in life. Sure, some left because they were sick of it, or sick of me perhaps – that happens. Nonetheless, when any individual quits in a small organization, it has an immediate effect; there is suddenly a hole to fill. Jobs have to be rerouted, future plans changed. I had people quit immediately after a 2 week vacation, or even while ON an extended holiday. While there’s never a great time for someone to leave a small organization, there are ways that are a little better than others. Ah well. Then, once someone leaves, the great search begins for the next person, which leads me to…

14. Finding Staff

I’d like to think I did a decent job of this over the decades, as I can really only think of one or two people who simply didn’t pan out. Still, every single time there was a job to fill, I had to solicit resumes (and figure out where to solicit, as well as how much budget to allot for advertising), review resumes, interview, and negotiate. In today’s era of automated resume submission, this meant I got a LOT of really inappropriate resumes. A lot of people submitting who really had no qualifications, or who had great qualifications for a completely different job. And I had a lot of headhunters calling me, trying to make their commissions by placing someone with my company. It always boiled down to a combination of skills and cost. Will this person provide reasonable skills at a cost my company can try to make money on? Another tricky and stressful task among so many. And that’s not even considering the ever-present issue of office culture. Hire someone to disrupt it, and it could mean someone else wants to find a new job. Like juggling chainsaws. That are on fire.

15. An Avalanche of Email

I am well aware that email addresses get snatched up and sold in bulk all the time, and this only gets worse the longer you have an email address. My company email was set up (by me, of course) in 1997, and remains unchanged to this day. That means that I’ve had my email address sold to untold numbers of related organizations, marketers, and of course, outright spammers and would-be-thieves. On a daily basis, I would have hundreds of messages that I had to sift through because they were at least somewhat relevant for me. That’s not counting the literal thousands of spam emails per day. Thankfully, I have tools in place to make the vast majority go away before I even see them, but the flood continues. Now, as I change my job focus, I am blissfully unsubscribing to anything and everything I can, plus, as you would expect, my volume of legitimate work email has dropped dramatically. I can’t explain how liberating it is…

16. Constant Contact

As technology evolved, so did our ability to annoy one another without delay. Still, while I always carry a smartphone, and I’m pretty much connected 100% of the time, it never failed that the moment when someone needed to talk to me was the exact worst moment. For example, given that I was the business owner, I intentionally made my home and office very close together – 1.25 miles to be exact. That meant that my commute was no more than 5 minutes. And invariably, in those exact 5 minutes, when I was driving and unable to answer, my phone would endlessly buzz in my pocket. Not one little buzz, but eight or ten in a row. Sure, I could check messages the moment I arrived, but to know that somehow, some way, the moment to contact me was exactly the wrong one? Ugh. Plus, having constant access to email and messaging meant that anyone – colleague or client – could contact me at any time, weekday, weekend, day, night, home or away. Clients would routinely ask me for my personal cell phone number, so they could get in touch with me whenever they wanted, and while I never, ever liked doing it, I always gave them the number because I ran the agency, and that’s what you had to do to make the client – you know, one of your MANY BOSSES – happy.

17. The Quirks of an Old Office Building

Obviously, this is specific to my job, but I bet I’m not the only person who has dealt with a creaky building. Our office, built in the 1940s, had the kind of electrical service where running the microwave and toaster oven at the same time would not only blow the fuse to the kitchen, it would power down an office where someone was working. Oops, there goes 3 hours of work, sorry.

Not to mention the water issues. Over time, water finds its way everywhere, meaning sometimes it’s running down walls, sometimes it’s dripping on heads.

Between electrical updates and water-proofing, we spent a ridiculous amount of money and time, and there remained issues.

The worst situation I ever faced was an evening of torrential rain. I had built a server room in the office basement, and intentionally had it raised 6 inches off the main floor, assuming that it would save me from up to 6 inches of unexpected flooding. One night, I had TWO FEET of flooding, and absolutely foolishly jumped in the water to save my servers from their demise. I managed to do it, knowing that if those servers were destroyed, my business was likely done for. In retrospect, I could have very easily been electrocuted that night. Thankfully, it didn’t happen. Still, sleeping on the floor of the conference room as a tiny pump tried to overcome pounding rain water by shooting it out an open door… that was no fun at all.

18. Wearing All the Hats

Jack of all trades, master of none. It’s both true, and not the entire story. I’d like to think I mastered a trade or two, but my job involved trying to be competent at virtually everything. Of course, I had strengths. Of course, I had weaknesses. But when you run a small company and you only have the people you have, someone has to pick up unexpected slack. Take a look in the mirror, friend. That slack picker-upper is you. Programmer, designer, writer, marketer, network engineer, database developer, SEO expert, systems integration specialist, project planner, presenter, client liaison, hand-shaking networker, HR chief, office culture czar, QA tester, debugger, on-site inspector, analytics agent, feedback translator, head of the team, and decider of all internal decisions. Chief cook and bottle washer, at your service.

19. Developing a Great Process, Only to Need to Dismantle It and Start Over

This goes along with the randomness of technology changes above, but I can’t even count how many times I spent the effort to create an effective process only to have to redo it relatively soon after. Internally, examples include the many, many hours setting up networks and servers to support the staff, only to soon need to upgrade them all (which was never a simple upgrade, but more like a do-over). Eventually, I outsourced them all to the cloud, but that was like another complete re-do. Externally, this means creating de facto guidelines on how to develop a client project, outlining exactly where to start and what to include, only to have the next half dozen projects have such specific needs that my guidelines no longer applied.

20. Better/Cheaper/Faster

That’s the old adage: better/cheaper/faster, pick two. Yet I know of so few clients who actually understood this. Almost universally, they wanted all three, even if they said they understood that getting something cheaper would mean they weren’t buying a Ferrari. How many times did I hear, “well, we understand our budget doesn’t support the complete functionality we want, but how do we get it anyway?” Actually, that means you DON’T understand. Often times, this would involve passing the buck. “Our board of directors is demanding the project have all the features we want, and be done at this budget, in time for their next board meeting.” I’ll admit, I probably tried to accommodate too many times. I don’t like to have relationships where I disappoint people. But over time, the realities of how this sort of work impacts everything made it impossible. There’s only one answer to an unreasonable question: No.

21. “We’re out of toilet paper”

This is a catch-all for all the mundane, necessary-but-stupid tasks required of a small business owner. I’ve replaced toilet paper, paper towels, light bulbs, ceiling tiles, batteries, computer mice, keyboards, monitors. Climbed under desks in a suit to figure out wiring issues. I’ve climbed on the roof to squeegee excess water toward the drain. I was in charge of specifying and buying every computer – desktop, laptop, and server – we ever bought. Plus, the supply closet doesn’t fill itself. I’ve had to keep on top of buying that toilet paper, and pens, and paper clips…

22. No Time to Focus

Every project I ever worked on required focus. Whether I was simply managing the project (“simply”? ahahahahaha) or doing development work myself, there absolutely had to be uninterrupted time devoted to that single project. Yet, the needs of the day continued to happen – colleagues needed my input or help, other clients needed information, things caught on fire, and even just random, unimportant conversations broke out. Any one of those things could derail me for a few minutes to a few hours to maybe even days.

Focus is critical. I’ve heard it said that there is no such thing as multitasking – there is only single-tasking with rapid changes in focus, meaning each task is done a little worse than it would be if you just spent time on a single thing. I think that’s true. Bouncing from one task to another very quickly diminishes the time and thought given to each task, to their detriment.

In writing, it’s the same. I have to consciously hide email and social media while writing, or else I’ll find my focus wander when that next email comes in, or when that next post shows up. At the least, this makes the task (storytelling, now) slower; at worst, it stops the flow completely, and you have to try again another day.

23. The Domino Effect

One thing bumps another and another and another, until they all fall down. Like when I had to take 3 hours out of my day to go to a pitch meeting, meaning that I couldn’t be present to oversee important work on another project before a critical deadline, potentially resulting in a problem that delayed delivery… which in turn might have stirred up a client’s ire, and delayed payment. And, once one project wasn’t completed on time, the next one couldn’t begin on time, so its deadlines also get pushed, as did payments for meeting those deadlines. Each domino knocks down the next, trickling off so far into the future with so many permutations that it’s almost impossible to anticipate them all. So you manage what you can, and you put your foot on the gas wherever you can. Sometimes you make up lost time, and sometimes you plow into another speed trap. John Muir once said, “When we try to pick out anything by itself, we find it hitched to everything else in the universe.” The same is true in agency work – if any one thing goes wrong, you find out it’s hitched to everything else you’re doing.


All of the above add up to one major thing in life: stress. If there is one single thing I’m looking forward to, it’s a serious and significant reduction in stress starting in 2020.

So here I am, beginning something wild and new, but happily shedding all of the above in favor of trying to succeed in something I enjoy. A new role of creativity that is placed on my shoulders, to succeed or not.

That’s it. Twenty-four things I won’t miss as I embark on a new career, an Act Two as it were for my working life. Maybe some of these resonate with you. If you’re a small business owner with staff, I suspect a lot do. What did I miss? In 20+ years, there are things that have come and gone that simply have fallen out of my brain…

There are countless happy memories from the past couple of decades, and there are some moments I never want to think about again. Nonetheless, it’s over. Next.

And now, back to writing my next novel.