Quitting Your Job Without A Plan: Employment Mistakes to Avoid

A B Taelor
9 min readSep 8, 2020


Most individuals will work at multiple jobs throughout their life. The motivation in ending one is typically to start another — and indeed nearly everyone would recommend finding a new one before ending the current one. But, that’s not how I do things… It takes a lot to leave reliable income, this for those of you seeking to learn vicariously from my situation or that are considering taking a leap of faith.

My Motivations

Despite what some may imagine, I didn’t hate my job — I actually enjoyed the work itself. Of course, some aspects were undesirable; but overall, it was a good job. However, over the course of nearly two years the situation slowly deteriorated. I went from standing as the top member of my department to the third on the totem pole. This wasn’t a sudden change, but rather a series of events that eventually led to the inability for me to continue working this job. If I could do it all over, I’d certainly change some things… I learned from many of my mistakes and I hope my employer learned something also.

Lessons Learned

Throughout my tenure with this company, I made mistakes that could’ve kept the strong perception my superiors had of me and enabled me to continue enjoying the workplace environment:

1. Don’t Burn Yourself Out — Over the course of several years I often worked sixty plus hours per week. I even worked over one hundred hours for six straight weeks at one point. Besides this, I was on call 24/7/365. I spent my entire workday working. That seems obvious of course… but I mean that I didn’t take breaks; I didn’t text friends or family or otherwise find distractions. This means I did not even eat lunch! I wasn’t tied to a clock and had to stay until the work was done, so, the faster I got it done the sooner I could go home. My motivation was drained, negatively affecting the quality of my work and changing my focus to minimize work as opposed to improving the operation.

2. Remain firm on decisions that are important to me — My managers wanted to promote someone internally that had reported to me in the past into a position that would report to me once again. Seeing as I had worked with this individual in the past, I did not want to move forward with them. However, my managers insisted this individual would be a great addition to the team so I relented. Flash forward and this individual was extremely knowledgeable and contributed a great deal to our operation’s efficiency — but they also created a lot of drama, misinformation, backstabbing, and general discontent. And, for a year and a half I had to deal with that… it made my life worse and everyday I was reminded of a time when my managers didn’t listen to me and when I didn’t stand my ground.

3. Hire people with a variety of experience — When our facility relocated, I hired two college recruits to fill out my team of four. While these individuals were talented with potential, it was too much for me to train them and for them to get acclimated. The operation suffered as a result, as did my reputation. I should have hired one of them and held out for an experienced hire that would’ve provided greater knowledge and contributions as soon as they got started. Not only that, but it would’ve allowed the individual to grow more measured instead of trying to rush their development.

4. Maintain professionalism — I allowed by displeasure with my managers affect how I treated the organization’s initiatives and people’s perception of me. It was not egregious, but on several occasions I should have reeled in my comments. I should’ve realized that people outside of myself were not aware how bad the situation was. By acting out, I was showing them that I was the problem, not my manager. Additionally, considering how dissatisfied I was, I should have left the organization far sooner.

5. Don’t indicate you’re thinking about leaving — Building off my frustration, I asked my manager if he thought it’d be better if I left. It shouldn’t have been a surprise to me that just a couple weeks later they announced they were hiring someone for me to report to. Again, considering how disgruntled I was, I should have left then since I was unable to kept my emotions to myself. By disclosing that information, my manager was given a reason to no longer prioritize my development (what little he gave me previously!).

Equally deserving of lessons learned, I hope my employer picked up on these items:

1. Communication! — Throughout my tenure, the communication within the staff was greatly lacking. I would often find out about new initiatives from someone other than my manager. Our corporate office would also release new policies or requirements without telling us and then we’d be blindsided trying to catch up. Not only demoralizing, but also dysfunctional.

2. Keep your team members in the loop — Carrying on the theme of poor communication… organizational changes should 100% come from no one other than your manager. But that wasn’t the case. On four separate occasions over the course of three years the company went in a different direction and I had to find out from peers or subordinates. Not only does that make me feel stupid and uniformed but truly unvalued as a high-ranking member of the operation.

3. Give all departments an equal importance and equity — Upper management and corporate stakeholders gave other departments greater importance, more information flow, and perceived favoritism. I don’t want to continue harping on communication, but I would often find out new developments from my peers in other departments (sometimes about my own department!). Additionally, other departments were invited to meetings about the operation and given perks (such as lunch) that wasn’t offered at all or as often. Everyone should be treated with respect but individuals at the same level should be granted the same amount of insight and decision making opportunities.

4. Don’t Waste People’s Time — Throughout my tenure, upper management set us on a path of projects that were not worth their while. But one stood out as especially egregious. Our corporate team put together a pricing efficiency program that we were meant to follow. That is all well and good, and understandable for financial goals, but the expected benefit only measured a few hundred dollars per month when our site’s revenue was typically north of $2.5 million. The program didn’t work well and we had to spend hours each week notating why it wasn’t working and explaining that to our corporate team — that’s in addition to the hours spent trying to implement this program that only angered our ground level employees. Finally after about a year and a half, they decided to pull back on the program and implement a softer version with nearly 80% of the benefits but hardly any manual intervention from the management team — now that makes sense! But the fact upper management isn’t willing to listen to the warning signs is beyond frustrating as it meant we had to waste our time on something that wasn’t worth it instead of improving things that actually mattered.

5. Create anonymous means of feedback from all levels of the organization — My organization was great at receiving feedback from the ground level, but not so much from their site leaders. It’s a bit of an oxymoron that the upper management would stress feedback so much and yet ignore it from their reports — but that’s what happened. Even when I got the feedback from the ground level and was filtering it up, I would get shutdown, ignored, or indirectly disciplined. My manager during my annual review told me to not say if I disagreed with direction but instead think “that seems stupid, but oh well…”. My managers were actively seeking to quiet any feedback I may have. Perhaps for good reason — if I was given the same opportunity to review my manager that my reports had to review me…

In the end, my decision to quit was due to disrespect at the workplace, disengagement with my day-to-day, and the desire to learn something new.

My Situation

To state it bluntly, I quit my job without having another lined up or even an alternative income stream. Taking this type of “leap of faith” would make most think I was doing pretty well financially. And I was, but not as amazing as you may think. I calculated out my monthly expenses and determined if everything went wrong, I’d be able to survive for 10–12 months without selling my house or dipping into my 401(k). If I did need to do that, I could survive for another twelve to eighteen months without securing a source of income.

I also set a limit to confirm when my dreams weren’t working out and I’d have to find a reliable source of income to continue my standard of living. With this understanding, I set forth with a plan for several ventures that I would attempt to gain financial freedom.

Given my lifestyle and reserves, I would have about four months to create a living for myself before I would need to hang it up and move on to something else. I resolved to set my eyes on “failing fast” — as much as I want to make this new lifestyle a reality, I was also afraid of becoming that years-long-failure who doesn’t know when they’ve lost. You have to take your hits as they come, rebound as best you can, and admit defeat when it’s apparent.

All of this is to say that I had the mindset prepared for this endeavor. Any other philosophy would be sure to fail, or fail to start. There’s no way I could’ve approached this differently. To not know my financial situation would be foolish and potentially disastrous. And to not understand that I could very easily fail would be pompous, which would in and of itself likely lead to failure. But knowing that I could fail, and still get up afterwards, was a relief and a lifeline. I would not be any less of a person, or any more, for having undertaken this initiative, regardless of the outcome.


So I didn’t completely quit without any idea of what I was going to do — but I did quit without a plan of how to do it. Considering my previous situation, I wanted to create income for myself (ie. Not have a formal / traditional job). I had to think, what ways are possible for me to make money without a boss? What will get me up in the morning? What excites me?

I came up with a few rough ideas — writing, stocks, business startups, free lance, coding. The problem with all of these is that they are all gambles and intermittent. None provide a steady paycheck. That was the biggest hurdle coming to an understanding with this decision — am I okay not making a steady paycheck? Ultimately, I was willing to take the risk and commit myself to struggle in the name of creating a better life for myself.

As is surely obvious by this point in the article, I am working to make a living by writing (enter critics stage right… and stage left… and center…). Luckily this has never been easier or more accessible as we have platforms such as Medium and Twitter, which have virtually no barrier to entry. It has cost me no additional capital resources and only time spent in order to write articles and post them — that is incredible.

I am still working to establish new income streams, and am working to find what will work for me. There’s no blueprint for this, no path to follow and only I can figure it out. Whether I fail at writing and try something else, or I fail at something else too, I’m confident that I will enjoy this time and that I will look back with some form of admiration (or ashamed laughter) at my decision and my time spent. As many have said in various forms, the journey is more rewarding than the destination.


“These Days, We’re All Disgruntled Workers.” Mark C. Crowley, 26 Mar. 2012, markccrowley.com/these-days-were-all-disgruntled-workers/.