Sink or Swim: Here’s How You’ll Know When It’s Time To Jump Into Self-Employment

Dana Little

Aug 23, 2017

It’s all about losses and gains (Hint: It’s not about money)

Working for a studio, company or school in a job you mostly love is mostly good, right? I mean, if you enjoy the arena you’re in, you’re pretty good at what you do, and you get paid almost enough to pay the bills, isn’t that enough? Well, maybe.

Can we all just admit that — sometimes — we find ourselves in a place of employment that is pretty darn good…even deceivingly so, that we get blinded for a while by the idea that pretty good is good enough? Jobs like this can seem (emphasis on seem) wise to hold onto for several reasons: we want to look responsible — heck, we want to be responsible (well, most days), and most of us are out there trying to make wise, reasonable decisions with our money, time and passions, right?

If you’re with me, read on. If you’re sort of with me, just give this a whirl and see where you land:

Pretend you’re considering an employment change. You’re toying with the idea of working for yourself as a private music teacher, yoga instructor, counsellor, or in that *one* field that makes your heart skip a beat just thinking about it.

While we’re pretending, let’s just pretend your current job is a ship. (Yes, in this paragraph and this paragraph only, a BOAT is the symbol for your present place of employment and YOU are currently on that boat as the lovely, dedicated — potentially worn down, burned out — employee that you are.) So, you’re saying you want to take a leap from the ship of safe-employment and land in the sea of self-employment? Well, you can, but remember: anytime you “jump ship”, you’re going to rock the boat.

It’s an age-old reality: You risk losing stability when you leave a current job. And who actually likes instability? I mean, when there’s no ship to keep us feeling safe and secure, it’s a little risky out there. No ship — right? ;)

All ship-speak aside, sometimes even the risk of instability or loss that comes from leaving safe-employment for self-employed is enough to keep you stuck in a job that’s no longer actually best for you, for way…too…long. Logically-speaking and all pretending aside, it’s risky to leave.

But I’ve been thinking: What if you risk losing more by staying put? What if, in your current job, you’re actually losing:

  1. Sleep and restfulness? Due to stress, dissatisfaction or a pesky feeling of overall “unsettledness” in your current job.

  2. Sight of your dreams? While you’re busy supporting someone else’s dream or business by being an awesome employee, if you notice you’re feeling a tiny bit too complacent in your current job or caring a little less about the details, that’s a hint that something might need to change. Or if you’re losing your previous sense of passion, enthusiasm or drive, it might be less about bucking up or grinning and bearing it, and more about the pull of your future, dream job. Don’t push your dreams away for too long or you might lose sight of them altogether.

  1. Time and patience? If it feels like being at work is a waste of time or energy-zapper, listen to that (zap!). If you catch yourself dreading the start of your work-week or spending time fighting someone else’s fires you don’t really care about, notice that nagging. If you’re dealing with tasks and processes you know you could do more efficiently if left to your own devices or you’re stuck in the middle of a workday that never ends (and where the heck is Friday?!), then — by all means — you’re losing time at your job and your patience is probably at least running thin. Drat!

But wait, there’s more (to life).

What if what’s best for you is actually a bold, brazen employment switcheroo? If you’ve already been considering a leap, here’s a look at how you could flip those “losses” on their heads and put a positive spin on #1–3 above.

What if a change of scenery in your work (you know…that place where you spend anywhere from four to six days a week?!) could help you gain:

  1. Sleep and rest! Imagine…the chance to wake up to a job you love or go to bed resting in the fact that you’re doing what you love five days a week (or more or less…because, hey!, it’s your dream job and you’re the boss!). Doing what you love gives you peace of mind, no?

Source: Source:

  1. Vision! Can’t keep your dream job out of your sights? Seeing you have more to give? If the idea keeps popping up about going out on your own to create a job with the perfect this-and-that, listen to this (and that). Or if the daunting task of setting up a studio that “feels just right” or a Saturday trip to IKEA to buy the perfect waiting room furniture for your dream workspace sounds “right up your alley”, don’t push that aside. (Also, don’t go to IKEA on a Saturday.) Perhaps you even catch yourself daydreaming about your next job while driving to your current job (even at your current job!). If so, that’s a tell-tale sign that you’ve got more to give. You have your sights on what’s next. You’re not greedy or a bad employee — you have vision!

  1. Your time back! Imagine going out on your own, doing work that you love, that you’re passionate about. The hours you put into it each week might be mind-boggling (you’ll likely spend more hours on “work” being self-employed than you do at your leave-it-at-the-office job), but it will be more fulfilling, less of that “watching the clock” feeling, and more of a sweet perception that the time you’re spending is valuable, because it’s where you want to be! And really, if you’re sensing that the time is creeping up to put your energy, talents, skills and heart into your work in a new way — that’s not back burner stuff. That’s when you know it’s time to start making waves.

Look before you leap: Some ideas to help you navigate where and how to land

Dana Little is a singer-songwriter, imaginative entrepreneur and teacher in Seattle, WA. Her colorful, cozy home studio, The Piano Parlor, points to her serious knack for bringing out the fun and whimsy when working with her music students.

When she’s not teaching, she’s playing piano, singing and writing for indie-folk duo, The Preservation Society.

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