Why should I leave?

I’ve been thinking more about how good employees are willing to quit.  It’s a big topic, and one that’s uncomfortable a lot of the time – most of us like to believe, deep down, that we’ve found a career that will last forever, we’ll always be happy, and we’ll never need or want to leave because we’ve got life figured out now, and nothing will ever change.

So we approach professional life with a couple of assumptions:

  • We should be employed all the time.
  • Outside of egregious offenses, we should stay at a single employer.

I’d argue that both of these are false – or maybe not false in the sense that the opposite is true (That people should actively seek unemployment, and should hop from job to job for no reason), just means that these assumptions are invalid.

Any relationship works best when all parties are on equal footing.  By accepting either or both of these assumptions, the employee starts at a disadvantage – assuming that they should always be employed (as opposed to self employed, or, you know, bummin’ around) and that leaving a job requires valid cause means at our most basic, we assume we need an employer.  This taints the relationship from the start.

 

Working under these assumptions, the question to ask is “Why should I leave”?  I think the correct question to ask is “Why should I stay”?

Obligation is the wrong reason to do almost anything, and assuming that the default is to stay in a job – to stay at an employer because you’ve been there for a while, because you owe them something, etc – is obligation.  It doesn’t get the best work out of anyone, and it breeds resentment, left unchecked.

The beautiful thing is that a shift in perspective here – going from the vague feelings of obligation and guilt that your job conjures because you think you’re supposed to be there, to the acknowledgement that you’re there for a reason: Maybe you really enjoy the work, or the people you work with, or you’re learning a lot, or maybe you just need the money (which is a completely valid reason to stay at a job) – can change your attitude completely, and clarify in your own head what you’re doing.

Alternatively, maybe you realize that there is no good reason to stay – that you really are just staying out of obligation, or because your mom likes to tell her friends that you’re important because of your title.  In which case, you can acknowledge that it’s perfectly acceptable to go figure something else out.  You don’t need a boss who sexually harasses you, or a job offer for twice as much money elsewhere – you just need an acknowledgement that there’s no good reason to stay.

Figure out why you do what you do.  It’s important.  It takes a lot of your time, and you only have so much.  You owe it to yourself to be honest about why you’re spending it the way you are.

 

Good Employees

I used to run a business that handled backups and security, or hack mitigation for websites and small businesses.  It was a good business, and I enjoyed it.  It started from nothing, and slowly grew until it could support me full time, without much extra.  But right around that time, I started running into issues – the business needed to grow, and in order to grow, it needed to change – to be lower touch, and scale better, larger.  We were at the limits of what I (as the only technical staff) could provide.

But that’s not what happened, because I needed money.  And when you need money, you start making the wrong decisions – prioritizing one-off deals that provide short-term cashflow over the slower, steadier work of scaling the business.  So that’s exactly what I did – a lot of individual deals, a lot of individual work that would get us by, month to month, but didn’t provide any lasting benefit, and didn’t really help the business grow.  Because we needed the money, we needed it to work, we stalled, and couldn’t continue growing.

I’ve been an employee now for several years, but I can see that the same concept exists here – with different consequences, different symptoms, but similarly dire outcomes.

Good Employees are not warm bodies

I’m grateful to not be in a business that just needs a warm body in a specified location, following well defined directions.  I’m paid not just to blindly follow instructions to get something from point a to point b – I’m paid because I’m a person with thoughts and ideas, who can offer insight and solutions to problems.  I don’t think I’m particularly unique in this.  My particular field, and employer do a good job of emphasizing autonomy and the idea that everyone is expected to think critically about the business – but I think deep down this is basically universal.  I think good employees, in most positions, and most fields, are hired not just to accomplish tasks, but because they’re smart, driven, and willing to give themselves to the problems and challenges a business faces.  An employee who just does the work asked of them as it’s laid out is a very smart robot, and will soon find themselves replaced with just that.

But I need this job

But there’s a conflict here.  Employers want their employees to be happy and productive.  Employees want to feel secure.  But often employees feel like they are tied to a job, to a company, for whatever reason – maybe they’re living paycheck to paycheck and don’t think they can afford the time it would take to find a new job.  Maybe they’re afraid they can’t find a job with benefits they’ve become accustomed to.  Maybe they’re afraid of starting over somewhere new.  It doesn’t matter.  As soon as someone decides that losing their job is a real risk that they’re unwilling to take, they’ll start acting to protect it – in ways that are often counter to the best interests of themselves and the business.

Honesty

Conflict is difficult for most people, especially conflict with superiors.  However – conflict, used constructively, breeds success.  A workplace without any conflict at all – opposing ideas, heated discussions, impassioned cases – is doomed.  Even smart people have dumb ideas, and if no one is questioning the people making plans, everyone will be worse for it.  If employees aren’t willing to stand up for what they believe in up to the point of leaving a job for it, it’s a loss for them, and for the business.  Passionate people do good work.  Agreeable people have a pleasant, comfortable time making garbage.

Balance

Relationships are subtle things, that require delicate balance.  To achieve full potential, that balance constantly has to be checked and tweaked, making sure that both sides are happy and committed.  The moment one side falls down and admits that they need the other too much, that they’re willing to accept too much compromise, that they’ll do work they don’t believe in as long as they keep getting paid, the balance is lost.  It doesn’t matter if there are good, caring people on both sides of the equation – when one needs the other more than is reciprocated, it’s impossible to work as well as it could.

Good employees are willing to quit

This is not to say good employees should quit jobs often, or early, or that an employee who has been somewhere a long time is bad – rather: in order to maximize productivity and satisfaction for both sides, the employee has to be as ready to quit as the business is ready to fire them.  Part of the employee’s job then, is to make sure that they’re always in a position – financially, emotionally, whatever – to be able to leave, and survive until they can find a new position.

So I don’t know, the least you can do is conspicuously keep a “go-bag”  with a couple of days worth of clothing and some beef jerky in it by your desk.  Just to let everybody know how ready you are.  When your boss gets out of line, just subtly point at it and raise your eyebrows.  Or, I guess, get your finances in order.  Less fun, but probably more effective.

The Treachery of Optimism

I used to own a business. It was successful, and I’m very proud of it – but it wasn’t a home run. Most of the time it was just successful enough to not be a failure. I paid enough of my bills every month to avoid serious discomfort. When things were good, we caught up. When life was expensive, we fell behind.

The service I offered – a backup and security product for WordPress websites called CodeGarage – came with stress. The code didn’t always work right, and when it went bad, people were occasionally left hanging. If customers got hacked, or new customers needed help cleaning up the mess left by hackers, they were impatient to see results and have things get back to normal. I worked a lot of late nights, cleaning up problems and helping customers. I enjoyed the work, but the stresses it created were not trivial.

Over time I grew tired of the endless financial stress, and felt like I was stagnating professionally. I wasn’t growing as a developer or a business owner, I was just keeping my head above water. In an effort to figure out how to keep moving forward, I applied to, and eventually sold CodeGarage to Automattic (the company behind WordPress.com), joining them as a developer. Personally and professionally, this was a huge victory; vindication that the hard work of the prior years was worthwhile. To top it off, Automattic was (and continues to be) a dream job — a company I had watched and admired for years, which turned out to be even better on the inside than it appeared on the outside.

Overnight, my lifestyle changed significantly. I had gone from a struggling small business owner to an employee. I knew exactly how much money I’d make every month. It was enough money, every time. I knew when it would hit my bank account. I even had health insurance. Real health insurance.

Not all the change was financial. I slept more, and I slept better. I was easier to be around. I could take time off. I lost weight. I could go an entire weekend without working. The release of stress and the accompanying benefits was not slow and gradual – it was abrupt, and obvious.

But somehow, things felt off. I was restless. Uncomfortable. In spite of the fact that I was making enough money to live comfortably, my work/life balance was better, and my stress was way down, I couldn’t shake the idea that something was missing.


My entire adult life had been about hustle: after eeking out a high school diploma, I floundered at community college. Soon after, I found myself working in a factory. I was unhappy, and I knew I could do better. So, in those long nights on the factory floor, I convinced myself that things could get better. Hard work could create a better career, a better life.

Struggle became my life, my mantra. Each step along the way was a victory – the first time I convinced someone to let me build a website for them. The first time I won a job on rentacoder.com. The first paying customers for my SAAS business. The most crucial piece though — the thing that made it all tolerable, even exciting — was the dream. Owning a big, self-sustaining business. Thousands of customers. Financial freedom. The big payout.

Struggling to get by, and to convince myself (and those around me) that owning a business is a good idea, I felt like I had to dream big. Working long hours and dealing with constant stress (financial and otherwise) didn’t feel worth it if the payout was just an unstable income, and less flexibility than a normal employee has.

As a business owner, it’s easy to believe that you’re just one big deal, one solid marketing campaign, one killer feature away from massive growth. This optimism isn’t necessarily irrational. CodeGarage saw at least 2 occasions that worked exactly like this: events, ideas, or sales that singularly propelled the business to a new level. Without the continuous belief that things will continue working out, and continue growing, I’d have quit or failed long before any money was made. This was the required mindset in order to keep going. However: it came with side effects.

Since I was convinced that I was just a few good decisions, ideas, or turns of fate away from greater success, I knew that these things would come to me. They’d happen, and probably soon. Success was not a question of if, but when, and more than that, it was “how soon”.

In practice, that meant I knew that within some period of time, the business would be successful enough that any of my current problems — work/life balance, money, stress — would disappear. So why bother worrying about them?

Assuming that impending success will solve all of your problems is a bit like praying instead of going to the doctor. It gave me the acute ability to ignore, or at least postpone dealing with problems. Financial problems (say, the massive expense of childbirth without maternity coverage, or poorly calculated tax liabilities) in particular were easy to ignore, as I was convinced greater success would soon solve them.

Of course, living like this is precarious. I slowly realized that while it did just take a few events to massively change a business, I might not have the requisite skills to facilitate those events, or I might not be able to learn them as quickly as circumstance demanded. Most terrifying, they might come too late. I was fortunate to land at Automattic, where I can continue to learn and grow. Maybe someday I’ll end up running a business again – this time with a new array of skills and tools to find success.

This brings me back to the vaguely unsettled feeling I developed after a time in my new, stable job. I had grown to believe massive (and most importantly, financial) success was just around the corner, all the time. In many ways, moving to my current job is that success I sought. However, it’s not “buy a yacht” success. Or “Own a second home at a ski resort” success. It is “Improve your skills working on interesting projects with smart people while not having to worry about whether your child can go to the doctor next month” success.

Having a job with a stable income, and compensation not tied directly to performance (at least, not in the way it is as a business owner) has meant accepting that I’m not going to buy a yacht next year. Conversely, it meant that I could buy a comfortable house this year. Much more importantly, it means that any financial problems I run into actually have to be dealt with, and not put off until the next theoretical deal can erase them. It’s a bit like losing touch with an old, fun loving, terribly irresponsible friend.

I’ll miss you, buddy.