4 Things I Never Thought I'd Love About Being Self Employed

When I first realized that I needed to become a business coach, I immediately also realized that it'd necessitate that I be self employed. This definitely came with the feeling of "oh god, I'll have to be self-employed." That feeling of dread about self employment seems to be not uncommon in the general population, and I'd like to posit that it may also not be uncommon among entrepreneurs. Even though I'd already formed my first business, I had not yet ever conceived of earning my living solely from my own business, and it did feel daunting. In the process of facing that fear, I've discovered many unexpected things about being self employed that I positively love. I offer this list in the hopes that prospective entrepreneurs might also discover a way through that daunting, fear feeling. 

Earning Each and Every Dollar

One of the most nerve wracking things for all prospective entrepreneurs, is where does the money come from? How do I land work that equates to 40hrs per week, without working 80hrs per week trying to find the work? This is also one of the easiest fears to dispel.

Here's the magical secret: when you charge more per hour, you can work less hours and still make the same amount. Let's say you're currently in a job making $50k per year working 40hrs per week. That means you're earning about $24/hr. So, if you're planning to be self employed in a service industry that charges $48/hr, then you can work approximately 20hrs per week and earn the same amount. Most service industries charge far more per hour; at $96/hr you could spend as little as 10hrs per week working in your business. (Or work a few more than 10hrs and give yourself a "raise"!) 

Obviously there's overhead expenses, marketing time, and taxes that need to be taken into account, but it's clear to see how the math works out in your favor. To ball park it, you need to figure out how to land a quarter of the work you're currently doing in order to break even. A quarter seems like a much more manageable number than earning every dollar.

Now that you have the secret, the unexpected win here is pretty obvious: work less, and earn more! 

Unstructured Time

When I was first looking down the barrel of self-employment, the "freedom" of not having a typical "9-5" did not seem like a good thing. I had enjoyed going into an office to work. Saying "Good morning" to co-workers was nice, and meeting the boss' objectives was a comfortable boundary to work within. I didn't "need" the "freedom" of self employment, and it sure seemed like there were some downsides in reduced focus and productivity. 

Unstructured time is definitely one of those things that trips up the self employed. You do have to have your own drives and impose your own sorts of structure. And just being aware of it is a huge help, plus there are tons of tools and tricks. Furthermore, if you're one of those independent type workers who doesn't need a lot of direction, then you'll do quite alright at managing unstructured time! 

As for not "needing" this level of freedom: sure, I guess I don't "need" it. And it's a really fabulous luxury that I never would have expected or asked for! I set my own hours which means I indulge my night-owl tendencies, and when clients cancel, I get extra long sleep-ins. I get to be outside during the day. I regularly cook myself lunch at my home. When I have a block of time to work on things I get to decide if I want to work from my sofa, a coffee shop, or my office. Sometimes I even take a nap in the middle of the day. This isn't to say that there aren't days where I'm not excited to work on the thing that really needs to get done, but I have options. And it's really easy to buck up and do something less pleasant when most days I sleep in and do work I thoroughly love.  

Business All the Time

I used to have this image of entrepreneurs as "always working" and that it took long hours and lots of stress. And that in order to "make it" you had to put every waking hour into the fledgling business. 

I'm here to say that is patently untrue. Do you have to put in a lot of time? Sure. But the funny thing is that now I have far more time to do the things I love. I think this is for a few reasons:

As I've already described, the number of hours I need to work *in* my business is relatively low, so the remainder of my "work time" is spent working *on* my business. And that time can often be organically broken up into non-eight-hour-day chunks and/or done at any time of day (or night, since I'm a night owl.) 

Working on your business can also coincide with other activities or chores, and can be timed for optimal efficiency. For example, laundry can be done while working from home on other projects, and a brain-break can coincide with a mid-afternoon trip to the grocery store, when lines are extremely short. 

I think we undervalue the time it takes to decompress from "9-5" work. In my self-employed life I rarely, if ever, work for 8 hours straight,  I'm doing things I love,  and I chose an office close to my home, so I spend almost no time commuting. All of these things mean I spend almost no time "recuperating" from my work day and that adds up to a lot more time that can be allocated towards productivity or recreation. 


I used to believe I was too risk adverse to become an entrepreneur. I had fears that I think everyone has when they contemplate self-employment: What happens if my business fails? I'm not in control of if my business succeeds or not, that's up to "the market." What if I can't pay rent? I have no safety net. I need a spouse who can support me while I launch this business; I can't do it by myself. 

Each of these fears makes sense, and that doesn't mean we need to listen to them. We can take a real, honest assessment and make a plan so that they are not true. 

First off, we always have to remember that we can go get another job. Maybe not our "dream job," but we can find some kind of work, pay rent, and move forward from there. We humans are a resilient folk, so we would only need to tap int that. 

Make a plan and have benchmarks and thresholds. This means taking an honest look at your resources and knowing when to call it quits (and knowing when to celebrate!) For example, when you've expended a certain amount of your savings, that you're closing up shop and taking the "get a job" route so that you're not destitute. Equally so, know when you're ready to leave your day job for self employment; you probably want to have some savings and a plan. Or know how many clients you need to break even and keep that goal in mind. As you get more on-the-ground experience, you'll probably adjust your plan. Make sure your benchmarks and thresholds adjust accordingly. 

Do a realistic resource assessment, and design and exit strategy. What funds do you have available to start your business? How much are your bare bones expenses (business and personal)? What options are available to lower expenses? What options are available to earn more easily? What back up funds are available? What's your plan if you close your business and your job search takes longer than expected? 

Finally, the truth is that you're not in complete control of if your business succeeds or fails. There are three ways of mitigating this fact: (1) having a well thought out plan (2) stress management tools such as meditation (3) turning this anxiety into the dedication to get things done. 

Managing the risk and the fears it inspires has left me with an unparalleled sense of confidence. I learned once that "self esteem" actually means to not only know what you do well, but also be aware of your weaknesses; it's an accurate whole picture of oneself. Being aware of the strengths and weaknesses surrounding my business has given me a type of self esteem about my business and a knowledge that if it fails, that does not mean I am a failure. 

Why Bother?

In summary, being self employed isn't for everyone, and I think it is far more attainable than people typically assume. In fact, many of these fears and potential pit falls are wonderful experiences that I hope everyone get's the opportunity to have some day. So, if you're thinking about starting a business, start making your plan. And if you need some help with that plan, well, that's what I'm here for. :)