Things no one tells you about following your passion

It’s now been exactly two months since I quit my job to pursue writing full-time, something I consider to be my passion and, like any good Millennial, should therefore follow. These past two months have been my learning curve, my awkward adjustment period, my h0ly-crap-what-am-I-doing-with-my-life-now flail. One thing I’ve learned is just how unprepared I was for the mental adjustments that come with leaving a “normal” 9–5 job. I knew life was going to be different, but I didn’t appreciate how very different freelancing is, often in ways that are much more subtle than being able to schedule doctor’s appointments during the day and needing to find my own health insurance. Here are four things I’ve come to realize in the last 60 days of “following my passion” that I wish someone had told me ahead of time (I don’t regret my decision at all, but it would have helped me gird up my loins against the challenge).

  1. Being your own boss is really, really hard.

When you work for yourself, you have to be your own employer and employee. You have to do both the high-level, strategic thinking to define projects and set priorities, as well as the day-to-day tasks and meetings and progress reviews that actually get things done. There’s nobody else to set expectations, give you recognition, impose consequences, or provide structure to your day. You become your own taskmaster, gopher, cheerleader, and HR department, on top of actually doing your work.

*(O.o)* ← Apprehensive panda

When you work for somebody else, your work tasks take priority over other things you might want or need to do, both because completing them pays your bills and because those tasks carry the added pressure of someone else’s dependence on you to get them done. If you don’t do them well, you let someone else down, which is added incentive to prioritize those tasks. As a freelancer, there is no “someone else” to let down: it’s only yourself. Your expectations are now the only expectations, and you have to hold yourself to them. This is very difficult when you’ve been working in an environment where the impetus to complete a task comes from a boss’ directive and the potential consequences if you don’t complete it.

I thought that I’d be instantly more productive at writing when I wasn’t answering to anybody else’s demands. But I discovered that with only my own subjective opinions to guide me, it’s hard to determine the relative importance of any one task. Is it a better use of my time right now to work on drafting a pitch of a story to an editor, or to realphabetize the spice rack? There’s no objectively correct answer, no existing policy to determine which has the better return on investment. Life is essentially a blank slate, and all possibilities are effectively equal until I determine my own priorities and implement strategies to achieve my goals. It’s a monumental responsibility (one that’s given me a whole new level of respect for good CEOs), and the struggle not to let myself slack off in the face of it is very, very real.

2. You have to create your own value.

Working for yourself means that many of the things you’re doing don’t have any intrinsic value to anyone but yourself. That’s one of self-employment’s most attractive features (finally, I can devote time to doing what’s really valuable to me!), but also one of its potential ideological black holes. With no validation that any of the things you’re doing matter in the grand scheme of the world, they can seem pointless, selfish, and a waste of time. Some people have a very strong sense of personal value and can just blaze ahead in these contexts, secure in the belief that because what they’re doing is valuable to them, it’s inherently worth doing. Would that we were all so self-assured.

When you work for a company, there’s a certain amount of value placed on your work. Generally, if you’re given a task to perform, it means that the company (or at least your boss) thinks that it’s valuable and, therefore, worth your time and your salary. The company’s goals and values become yours by extension, which is one of the most common sources of worker dissatisfaction: a disconnect between what the company values and what the employee values. However, without an employer defining what is of value, suddenly your own personal goals and values become the driving force of your entire life. This is simultaneously empowering and terrifying, especially if you’re someone who is used to putting employers’ values and tasks first, at the expense of your own (me).

Having a “normal job” masked the fact that I was chronically failing to achieve my personal goals because I was prioritizing tasks that my employer determined had value. Now, without that external determinant of value directing my activities, I have been forced to recognize that I’ve been consistently letting myself down, that my personal values have been subjugated because it was easier to let my employer determine them for me. Now, I am that employer, and I have to determine the value of pretty much everything in my life. It’s not an easy task. Also making it more difficult is that I have to re-train myself to treat my personal goals and values with the same respect and authority that I gave to those set by employers. Essentially, I’m trying to live out Polonius’ maxim, “This above all: to thine own self be true.” Easier said than done.

3. Relationships are important, even if you work better alone.

I’ve always been someone who’s gotten more done on their own. In high school I was that kid who would sit on the floor of the hallway to study during free period while my classmates hung out in the common. In college when I had to work on team projects I ended up doing the majority of the work, because my teammates were less focused than I was on getting the assignment done well and efficiently, which further turned me off to working with others. Then, when I entered my first “real” job after college, I was suddenly faced with 60 coworkers with whom I was expected to work and socialize, often at the same time. In my head I had consciously separated those two activities completely, and I didn’t really know how to wrangle them into co-existence. If I put my head down behind my cubicle walls and worked for a few hours straight, I felt like I was missing out on the office social scene and inviting the labels of “antisocial” and “not a team player.” If I lingered at a friend’s desk on my way back from the kitchen or joined an impromptu yoga session in the hallway, I felt guilty that I wasn’t doing work. The end result was that I felt constantly on edge when I was at work, no matter what I was doing.

I thought that becoming a freelance writer would resolve that issue because I could focus completely on my work without the expectations imposed by having coworkers, which would then allow me to relax and socialize with my friends knowing that I’d put in a good day’s work. But being alone for so long has made me realize that, actually, having people around you when you work is important. There are several reasons for this:

  • Being part of an organization or team working toward a common goal generates camaraderie and provides an underlying connection that is difficult to create with people de novo. You might not share your cubemate’s penchant for fantasy football, but if you’re both doing a similar job at the same company, you probably share some skills, values, and interests that allow you to have good conversation over drinks together after work. Your coworkers might not become your close friends, but they’re a group of people with whom you share something significant (namely, your livelihood and how you’ve chosen to spend 8+ hours of your day) and who can provide the human connection we inherently desire.
  • Because coworkers are not necessarily people you would have chosen to hang out with on your own, you can learn a lot from them. In a team setting it’s expected that everyone find ways to work together effectively, which means team members have to learn about each other and build a rapport that allows them to do their collective job well. In order to simulate your brain with other minds, voices, and opinions, you have to go out and find or create your own community, on top of doing your work as a freelancer. Goodbye, pajamas; hello, real clothes.
  • No matter how hard you work on your own, teams are just inherently more productive than individuals. Everyone has strengths and weaknesses; when people work together, they help fill in the gaps in each other’s abilities to collectively function like one big superhuman. Yes, Steve Jobs is hailed as a genius who came up with many of Apple’s life-changing products in his own head. But without a strong team around him to implement those ideas, he wouldn’t have gotten very far. That’s why companies exist: to achieve something that no one person is capable of achieving. When you work by yourself, your productivity is limited by your own skills, time, and energy; something that can be frustrating to realize and make you feel like you’re not reaching your full potential.

Basically, relationships with other people are important, and coworkers come with the built-in potential for relationships, both in the work environment and beyond. It’s entirely possible to create relationships when you’re working on your own, but it takes a lot more effort.

4. Work is still work, even when it’s your passion.

A lot of articles and books targeted to the Millennial generation, which is routinely perceived to be suffering from crippling uncertainty about their careers, espouse the advice attributed to the ancient Chinese philosopher, Confucius: “Choose a job you love, and you will never have to work a day in your life.”

Having tried this for a few months, I’d like to respectfully call this out as bullshit.

It’s not that simple. Just because you have chosen a job you love does not mean you don’t have to work. It doesn’t mean that everything will suddenly be easy and you won’t have to make sacrifices. It just means that the satisfaction of doing your job will outweigh the challenges and difficulties you face in doing it, so that you achieve a higher level of overall happiness. You still have to work.

When I started my foray into freelancing, I was excited about actually taking the time to do all the things I had been putting off for months or years. I was going to finally write and publish my travel blog posts that are nine months overdue! I was going to make a personal website! I was going to organize all my photos and put them into nice albums on said website and make prints available for purchase! I was going to play the piano again! And without anything else demanding my time, life would feel like one long weekend, where all my time was spent doing what I wanted to do. But now, two months in, I haven’t done any of those things.

Why? It turns out that weekends are much less productive than the work week. To convert your personal and leisure activities into your career, you have to treat them with the same discipline and effort you would a “real” job. Yes, freelancing allows me to go to a Zumba class at 11:00am if I want to, but that means I have to write for two extra hours in the evening to make up for that break in the middle of the day. Sometimes I have to say “no” to weekend Ultimate frisbee tournaments because I want to write a feature article for Medium. The distinction between “work” and “leisure” exists because they’re both necessary for getting things done: passion-following demands the discipline of a job and the enthusiasm of a favorite hobby.

There are good and bad aspects of re-casting passion as profession. On one hand, it can make you dislike something that used to be a unilaterally positive experience. Writing, which I used to only do when it gave me enjoyment, now sometimes feels like a chore. However, on the other hand, pursuing your passion professionally means applying a certain kind of work ethic and attitude that can allow you to actually excel at it, which provides a level of satisfaction and achievement that you simply can’t reach if you’re in a job you don’t love. But it’s still a job, and don’t let anyone tell you differently.