Becoming Self Employed and In Control of My Own Life

Last Updated on January 5, 2021

Last updated: May 3, 2018.

A few weeks ago, I decided that my efforts to find a traditional job was getting me nowhere.

Despite cutting back my criteria down to simply trying to find something I don’t hate (regardless of pay, hours, or type of work), it’s been over 3 months since my last job interview. And once again, I was crushed when I didn’t hear back from the only other promising opportunity since then.

The constant rejection was getting to me.

Even though I tailored each application to the job (sometimes spending hours doing so), I’m sure my lack of confidence was still somehow evident. Every unanswered application made me want to give up – so that’s exactly what I did.

I gave up.

I gave up feeling sorry for myself.

I gave up wasting 40 hours a week obsessively checking job boards.

I gave up applying for jobs I didn’t even want.

I gave up thinking that my career potential was in someone else’s control.

Instead, I focused on becoming self employed and in control of my own life.

Unlike a lot of other bloggers I know that have left the 9-to-5 type jobs behind, my definition of “self-employment” does not focus solely on earning an income online. While working from home is extremely appealing to me as a homebody, I know I’m not ready to do just that. Being home all the time was part of what caused (or at least added to) the slump I was in, and I don’t want that to happen again. I need something that gets me out of the house, at least sometimes.

Therefore, my self-employment also includes things like babysitting, pet sitting, and tutoring.

Of these, the easiest transition for me and the most in-demand role is babysitting. Which is why it made up the majority of my income for what I’m going to call my “first month of self-employment”.

Although I’ve been supplementing my un(der)employment with my blog and related online work for over a year now, making money online was never my focus. It was a hobby that just happened to bring in a bit of income, too.

My approach was very casual. I didn’t have any goals in mind or any semblance of a plan. I just wrote about whatever was going on in my life, published posts sporadically, and hoped someone would use one of my affiliate links or click on an ad so I’d earn few bucks. This approach was vaguely successful, as I made about $500 between January and July of this year. (Although, more than half of that was from answering surveys on Swagbucks.)

When I decided to really give this a shot, I knew that I needed a plan. I needed to set a goal to help keep me motivated and accountable.

I settled on $1000 a month as a starting point.

It’s a challenging but realistic goal and is roughly equal to what I made at my last job, so at the very least I’m not moving backwards.

How did my first month of self employment go?

The Numbers

Unfortunately, I didn’t reach my goal of making $1000 in August. But I was pretty close.

I made roughly $875.

Of that income, only 20% came from online sources.

Making enough money online to replace the income of a more traditional job is going to take time. I wish it was just as easy as (finally!) posting a Hire Me page, but let’s be real. It’s a good step, but the jobs aren’t going to magically start rolling in from that alone. If it were that easy, everyone would be doing it, right?

Majority of this income has been thanks to the friends and connections I’ve made online (extra shout out this month to Vanessa and Anne!). At least once a week, someone I only know online sends me a job posting or advertising opportunity. The majority don’t work out, but I learn and gain more confidence with each exchange and attempt.

The remaining 80% of my income came from babysitting.

When I was first laid off, I thought about getting back into babysitting, as I’ve always loved working with kids. But I never pursued it. I was still hanging onto the assumption that I’d be re-hired at the college and foolishly didn’t take my unemployment seriously.

When I wasn’t re-hired, I should have explored this route instead of sort of reluctantly taking the job at the gym’s daycare. I had no idea how many people were/are looking for reliable childcare. Or that some pay more per hour then I made when I worked at the theatre!

I asked my friends on Facebook to keep me in mind if they were in need (or knew someone who was) and created a profile on a childcare website that I often saw on other job boards.

And it was literally just that easy.

Within a week I was watching an old childhood friend of mine’s kids for the weekend. Shortly after that, I was hired by a young family looking for regular part-time care for their 2-year-old daughter. This gig alone earns me about 75% of what I made at the daycare, in 50% of the time. They take off all the proper taxes and deductions, which saves me from having to tax myself. (Although using software like FreshBooks would make it easy to handle by myself, should I need to.)

And I’m not miserable, or constantly getting sick from it, either.

The Impact

Okay, so earning $875 a month isn’t great. But it is better than the nothing I would likely be earning otherwise. And it’s enough to keep the bills paid.

I’ll be honest, though. I was hesitant to include the numbers in this post because it is embarrassing to share with those that may not know my story. But I decided I need to be open about it. A part of me is hoping that in the not-too-distant future, I can look back at this starting point and see how far I’ve come.

After all, when Michelle of Making Sense of Cents started tracking her online income back in May 2012, she only made $362 but is now making 6-figures each month!

I probably won’t ever reach a milestone like this, but for the first time in a long time, I’m actually feeling confident that I can make a living on my own terms.

More importantly, though – I’m happy.

And that is extremely liberating!

I can’t remember that last time I’ve been able to say that about my work life. And I can’t believe how much of a positive impact it has already made on every other aspect of my life, as well.

This is just the beginning.


YOUR TURN: If you are self-employed or have a side hustle, do you set financial goals for yourself? If so, do they help keep you motivated or do they just cause you stress?

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Amanda Kay

Amanda Kay, an Employment Specialist and founder of My Life, I Guess, strives to keep the "person" in personal finance by writing about money, mistakes, and making a living. She focuses on what it’s like being in debt, living paycheck to paycheck, and surviving unemployment while also offering advice and support for others in similar situations - including a FREE library of career & job search resources.

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24 thoughts on “Becoming Self Employed and In Control of My Own Life”

  1. I am so excited for you!! I love being self-employed BUT I have very, very specific socialization targets/goals for each week so that I don’t become a weirdo. Basically, I have to do something social no matter what. My social life ROCKS now. As for income, the months that I tracked my income-it grew. Pure and simple. Then months I didn’t track it…it shrank and it was very easy to lose track of everything. I will always track my income from now on. I never want to feel broke again. It sucks.

  2. $875 is aweome! A step in the right direction. I’d be interested to know how much more you have to go to replace your part-time day care income and then ultimately your income at your old job at the college! Good luck on your journey!

    • After expenses, I’d say I’m about even to what I was actually making at the day-care. (Since we were spending $100-200 each month on taxis, which we don’t have to worry about anymore.) To replace the college, though… that’s going to take a while!

  3. It’s not embarrassing at all! I’m really happy to see the progress you’ve been making, and $875 can certainly make a dent in your monthly bills. Like you said, it’s only the beginning. I too have recently decided to explore self-employment, and it’s amazing how powerful your existing networks can be. I’ve gotten some amazing leads from my existing contacts and look forward to seeing where it takes me.

  4. Good for you. It’s interesting because I have followed various bloggers who have gone into the land of self-employment, the common thing is that everybody starts small. Nobody starts Day 1 making $10,000 per month. But some get there. No guarantees either way, but the point is that starting small is the standard. Good luck taking it to the next step!

  5. Michelle @Making sense is a rock star. She is very transparent about how she does it and I still don’t know how she does it. Anyway, glad the childcare thing is working out. It is so true that there are always people who need reliable childcare providers they can trust and doing it for yourself is way better than doing it for those folks at the gym. It’s a start and at least you are bringing in income. I’ll be in your Country next week. Only for a day! (btw-it’s seems so weird to me sometimes that Canada is another country).

    • Welcome to Canada! (Or have you left already?)
      I don’t really get how Michelle does it either, but I’m learning each day! And it is so much nicer to not have bad managers any more.

  6. I’m so glad that you’ve made the leap into self-employment and that you’re enjoying it! It can be tough to get over the fear of not having a more traditional source of income, but self-employment has so many benefits and no limits!

  7. Amanda, I totally feel you! Stepping out into self-employment can be scary but totally liberating at the same time. And you can absolutely be proud that you made over $800. That’s amazing! Every dollar counts and everyday you work harder on being completely self-reliant in your own small business is a successful day in my book. Thanks for sharing your journey; it gives me hope for my own.

  8. Wow, this is amazing. Good for you. In my city, quality child care is difficult to find and because of that extremely in-demand. I think it is a wonderful career path for someone who loves children, like yourself. You can set your own hours (mostly) and work as much or as little as you like. I think this is a wonderful balance. And it makes you happy, nothing is better. Keep up the good work, you are doing great!


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