How To Be Stress-Free And Self-Employed: 5 Lessons I Learned About Being My Own Best Boss

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Download the free worksheet below (See Lesson 2) - “Calculating A Job’s True Value - Is That Job Really Worth Your Time and Energy?”

The Sunday blues are real, but they don't have to be.

You can actually be excited for a new work week, with just a few simple tools that will help you manage your workload and stress so that you can be the best damn you, you can be!

I used to hate Sundays. I would get major anxiety, maybe even a bit depressed, about having to go back to work.

At the time, I was working full-time (plus evening events) as a busy communications professional, and during the last few years of my career, I was also working up to 20 hours per week as a part-time Pilates teacher.

I took the leap to become a full-time Pilates teacher. Now, you might think, 'you teach Pilates... not exactly a stressful job.' True. I am lucky. However, I also had to pay the bills... as a Pilates teacher. (Cue the stress.)

It was a rocky start, and I had to learn some important lessons about how to create a life that made me happy and paid the bills.

I can honestly say, I am now excited for Monday. I can't wait to see my clients and just welcome another awesome week. I have very little stress, and the stress I do have, I eliminate or manage.

Here are five of the most important lessons I learned during those first years as my own boss.

I think they can be applied to many situations, whether you are managing a side hustle, or your kids' activity and social calendar, and I hope they help you eliminate a little stress in your life.

If you have any to add, please comment below!


1. Diversify. Don't let one client, employer, account, or situation "own" you:

When I first started teaching, I threw a lot of eggs in one basket, and that basket was a complete headache.

This one particular area of my work world was polarizing, causing me tons of anxiety and stress, and affecting all the other aspects of my professional life.

It was making me unhappy. And let me tell you, I didn't choose this profession to be stressed out. For that, I'd go back to the corporate world and get way better benefits.

I realized that the best way to deal with the situation was not to leave it completely (there were parts I really liked about it), but to give it less importance in my psyche by giving it less importance in my big picture.

I cut my hours from that basket and diversified my income portfolio. And it helped. That basket has since been rearranged and it is now my absolute most favorite basket (did I lose you on the basket analogy?)

Anyway, the point is, I learned that if I knew I could leave something at anytime, it couldn't cause me stress. Make sure that if any one thing changes or goes away, you will still be ok.


2. Time is money.

In the spirit of diversifying, I was running all over town trying to get as many hours in as I could.

Since I don't have a car, I was paying for Uber. Sometimes I would teach just one class, but waste three hours with travel time.

When I ran the numbers including travel time, and subtracted my Uber rides from my pay, I might as well have been paying to work.

I learned to calculate the true value of every opportunity with travel time. I would also consider the wider the promotional/marketing value of the opportunity (could this lead to more business in some way).

And finally, I’d think about how much I actually liked the job. Didn’t it cause me stress or make me happy? Was it fulfilling? Was I learning and growing because of it?

I would divide the pay of each opportunity by the real time, and if it didn't make sense I would cut it out. I now can work fewer hours, making more money.

Make sure you are calculating your actual hours on a job; not just time physically working on that job, but also the time it keeps you from being able to work on another. Marketing value, stress or happiness, educational value, contacts it brings and other non monetary factors should also be part of the equation.


Download the Worksheet

Is That Job Really Worth Your Time and Energy? Or could you be making more money, working fewer hours, and with less stress?

Use this worksheet to quickly calculate the true value and actual hourly rate, including non-monetary considerations like stress and marketing value, of any job opportunity.


3. Set your limits.

When I took the full-time teaching leap, I felt like a slave to my clients' needs. I was at their beck and call and would make myself available according to their needs and schedule.

My schedule was like a checkerboard, and I was running around like a chicken with its head cut off.

It wasn't working. I was tired and snappy, and I wasn't happy.

I learned to make blocks of time when I wanted to work, and to fit my clients into the schedule that worked best for me.

If they couldn't do it, then they weren't a client for me. (But most did.) I considered how many hours I could work in a row before needing a break, what times of day I was most "on," and how many hours I wanted to work.

I found clients that worked within the parameters that I set for myself, and learned to say "no" to things that didn't work for me.

You can't pour from an empty cup. Learn to say "no" to things that don't work for you. Refer the business out to someone who is a better fit. It won’t be a wasted opportunity. Both the customer and the person you refer them to will likely remember you in a positive light and may return the favor. If you want to be 100% for your clients and customers, you have to establish your limits and stick to them. Read: 5 Healthy New Years Resolutions You Can Keep


4. It's ok to let some clients walk away.

There was a time when I felt like I had to "sell" Pilates to everyone, and move heaven and earth to keep my clients.

But over time I found that the people I had to convince or made exceptions for often didn't stick around that long anyway, and they definitely didn't see or experience the full potential in the work.

I learned that if people don't see the value in what I do or don't value my time (disrespecting late cancel policies, asking for discounts or free classes, etc.), then they're not my clients.

The stress that I would feel from certain clients would carry over into my other sessions and it wasn't fair to my other clients. So, I learned that you can't force it.

It can be scary to let people walk away, but it‘s necessary in order to make room in your schedule and life for a better and more natural fit for you both. Don't burn any bridges or leave clients with negative feelings about you or your business in any way. Leave the door open. And, you'll be surprised how many people actually come back, ready.


5. If you don't value what you do, no one else will.

Friends and contacts are the best source of new client business, but it can be uncomfortable when it comes to charging them or talking money.

I have learned that you have to set your rates and stand by them.

None of that, "...well, I generally charge X, but for you...." NO. Just don't do it.

A small, consistent discount across the board for a certain population that you carefully manage and calculate is one thing. But never let people negotiate your rates.

Stand by your policies and don't make exceptions. State your rates with conviction, cut out the stuttering and backpedaling, and know that you are worth it.


These are hard lessons to learn, but once I implemented them in my work, everything fell into place. Have you had any similar learning situations? I would love to hear them in the comments below!

Early version originally published November 1, 2018.

Read: My Pilates Story: Pilates Saved My Life