Sometimes placing two words together completely changes their meaning in surprising ways. Add the grimness of rain to the, uh, curviness of bow, and we get a beautiful rainbow. A charging bull plus a sleepy dozer makes a relentless pushing machine.

And, the violence of slash plus the tedium of career makes for a fascinating way to live your life. But don’t worry—a slash career isn’t about serial killing. It’s a concept from Emilie Wapnick’s book to describe mixing interests into a unique profession of your own, as in “I’m a teacher slash juggler slash personal trainer.” Similar in concept to a “portfolio career,” this is a popular career model these days.

I discovered this idea over a decade ago, as I sat in a coffee shop and dreamt of how my life might look if I made the scary decision to quit my full-time job. I vividly remember realizing with some surprise that my next step didn’t actually have to be another full-time job. I dared to ask myself—for the first time ever—if I could work part-time while writing books and teaching and giving talks and experimenting with other projects and…

It took some years, but I was eventually able to live my slash career dream. And, at times, it really was a dream. I loved always being able to choose how to spend my energy.

But it was also hard. Not only did I have to contend with the difficulties common to everybody—namely, there was never enough money, time, or energy—I also had troubles particular to the slash career. After about seven years, I was ready to make another big change, and last year I—gulp—returned to full-time work.

Happily, this wasn’t a complete retreat from my dreams. I now have a traditional job which is full of variety, and which gives me the freedom to dabble in occasional fun projects on the side.

Now that I’m firmly into this new chapter, I’ve been reflecting on my slash career experience. I’ve realized there are several things I consistently lacked during those years, and I wish I’d known about them in advance. If you’re in a slash career of your own, maybe you’ll recognize some of these too?

1. Lack of mentors & colleagues

The closest thing I had to colleagues during those years was the Puttyverse community. But even with their friendship, it was lonely being the world’s only custard-based mental health comedian/programmer. My fellow multipods understood the difficulty of juggling disparate disciplines, but few understood the specific mix of things I was dealing with. 

I also found it impossible to find mentors within any particular area. Advice from other comedians was rarely helpful because our problems were so different. I wasn’t trying to build up my comedy reputation, get bigger gigs, or get onto tv. For me, comedy was about having fun while doing sporadic paid gigs. Similarly, the advice I often got from other writers and software developers was to be more dedicated and to write/code more. This was great advice in their context, but it only served to make me feel guilty—I was inevitably always neglecting something.

As a result, I struggled to find anybody who could reliably tell me when I should be shifting my focus, and I was left to rely on my own imperfect guesses about what to prioritize.

I never found the perfect answer to this problem, but two things did help. First, even though multipods were juggling different sets of activities, talking to them was always useful. They shared my problems of loneliness and difficulty choosing where to focus, and it was helpful to have both a sounding board and a place to vent. 

Secondly, I found it invaluable to mentor others—both multipods and people within each of my areas. Not only does mentoring benefit the overall community by solving my original problem of “too few mentors,” but focusing on others’ difficulties often helped to shed new light on my own problems. I’m sure you’ve also had the experience of giving somebody else advice only to realize the same advice would be helpful to you? Mentoring gives you the opportunity to learn from your own advice on a regular basis!

2. Lack of safety net

What counts as a “safety net” varies massively depending on the culture you live in and the circumstances of your life. But prior to adopting a slash career, I was accustomed to many of the trappings of “proper jobs” in my country: nearly two months of paid leave every year and automatic pension contributions, for example. 

On leaving my full-time job, I was suddenly responsible for my own long-term savings. Worse, time off meant less money, so I was constantly either stressed, or guilty… or both.

Clearly, this isn’t easy to solve, either at the community level or individually. If I could have single-handedly instituted Universal Basic Income in my country to unlock the potential of these sorts of careers, I promise I would have. Unfortunately, all non-systemic solutions involve unrealistic levels of luck or generational wealth, like a medium-sized lottery win or surprise inheritances from distant relatives.

Assuming societal change isn’t within our immediate power, all we can do as individuals is make rational choices given our circumstances. I was lucky, in that some pillars of my slash career were capable of supporting the others. In particular, writing software was able to support writing books. I was able to dial up and down those two aspects according to my needs at the time. And later, as my speaking career took off, I developed two aspects that could support the others.

In short, the lesson here was that it was crucial to ensure my slash career always included at least one aspect that reliably brought in income. This may sound obvious, but its inherent tradeoffs make it less so. Generally, these income-generating pillars are the ones we are trying to move away from—often because they’re difficult, unpleasant, tiring, tedious or uncreative. It feels counterintuitive to rely on these aspects when we may be trying to escape them.

Money is always a thorny issue but these choices are all about tradeoffs, which means we need to be aware of their inherent dynamics.

3. Lack of growth

The nature of juggling disparate careers is that you’re only ever growing in one at a time. Months spent writing a novel would cause my programming skills to fall behind. Months on a large programming project would atrophy my public speaking skills. Worse, it was common that my most reliable income was highly repeatable, so I spent a lot of time churning out similar work for different clients, and I struggled to grow in that arena too.

Paradoxically, I have also written about how to juggle many skills without falling behind. It’s easy to say now, but looking back I wish I’d been more conscious about pushing myself to grow in each skill, and been more creative in smooshing skills together.

What to do when you’re struggling with a slash career

All of these disadvantages may sound grim, or even fatal to our dreams. Certainly, years of living with any kind of significant deficit can leave us jaded. At times, I got pretty disillusioned and I often wondered if I’d made the right choice.

This is okay, and it’s normal. To be fulfilling, any career model has to be an intentional choice—and we have to keep choosing it, disadvantages and all. If our career style isn’t fulfilling any more then maybe that’s a sign that it’s time to take stock and consider other options.

These options are, briefly:

Be positive

It’s worth remembering that we get into these slash careers for a reason. To steal a nice quote, we choose this lifestyle not because it is easy, but (partly) because it is hard. 

And also because it’s super interesting and fun! Sometimes I had to remind myself of how great my lifestyle really was, even in the midst of disillusionment.

Identify the problem(s)

Looking back, I often lacked clarity about what was sapping my morale. The problems above seem obvious to me in retrospect but weren’t always visible at the time. For example, figuring out that I was lacking mentors might have helped motivate me to go out and find some!

Accept the situation as-is

Tradeoffs are inescapable, and sometimes the benefits are worth it.

Experiment

Portfolio careers almost always require revision and evolution to make them work. It takes time to find the right combination of part-time revenue streams to get enough money, meaning and variety. Switching one slash for another can provide a much-needed boost of motivation—and hopefully success too.

Switch models

Eventually, something came along for me which fit better with my goals and circumstances, and I’m loving my new model right now.

Whether you’re deep in a portfolio career of your own, contemplating a switch, or are simply interested in how others live their lives, I hope these reflections on my own slash career experience are helpful!