6 Lessons I've Learned in 2 Years of Self-Employment

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Today marks exactly two years since I quit my full-time job to become self-employed.

Exactly two years ago, I was saying my good byes and packing up my office to head home for the last time.

I was scared, nervous, and excited about my new adventure. I’m sure many people thought I’d fail.

Taking the leap to self-employment with $148,000 of debt and only a meager $3,000 in savings (emergency fund and business savings combined) was the scariest and best decision I’ve ever made.

Most people “didn’t get it”. Some still don’t. They don’t understand that real money can be made online, even though I’m making 5-6X as much as I was at my day job.

But, even though I’m earning more than I thought possibly from my blog and online business, I’ve still got lessons to learn. I’ve learned a few the hard way already and I want to share them with you so that you might be able to learn from my mistakes and avoid them. 🙂

Here are 6 lessons I’ve learned in 2 years of self-employment.

1. You Have to Work to Get Paid

Duh! Right? Well, let me tell you, one of the hardest things to learn when you’re self-employed is that you have to work to get paid.

There are no more paid days off, sick leave, etc. You don’t get paid for sitting in the break room talking to co-workers or surfing Facebook either. The only time you’ll get paid for is the time you spend on billable projects.

This is why it’s so important to limit the time you spend on unpaid tasks. You’d be surprised how many tasks are unpaid. Seeking new clients, preparing proposals, sending pitches, promoting your published work, writing for your own blog, and sending invoices.

These things are all very important to keep your business running. But, you need to make sure to do them as efficiently as possible since they are unpaid.

In my two years of being self-employed, I’ve learned to use a few tools to help me save as much time and money as possible. One of my favorites is Freshbooks because it helps me save a ton of time and money.

You can try Freshbooks free for 30 days with my link.

2. You Have to Earn More Than You Need

This is something I talk about almost every month in my online income reports, but I’m going to say it again. You have to earn more than you need when you’re self-employed.

What I mean is, I don’t get to keep every penny that my business earns and put it into my personal budget. In fact, I probably get to “take home” 50% or less of how much my business earns each month.

A lot of people forget that you have to put aside 25-30% for income taxes.

Plus, when you’re self-employed, you have to pay for 100% of your own health insurance, retirement savings, etc. These are things that traditional employers usually help out with.

You’ll also incur business expenses to pay for training, conferences, outsourcing to contractors, new tools, etc.

3. You Don’t Have as Much Freedom as You’d Imagine

Another tough lesson to learn is that you don’t have nearly as much freedom as you’d imagine when you’re self-employed. Because you have to work to get paid, it’s much more difficult to take a day off and have a flexible schedule that you think.

At least until I’m debt free and caught up on some of my other financial goals, I have to keep working a full-time (or more) schedule.

I can raise my rates to help me earn more for the same amount of time and effort. But even with higher rates, I still have to be creating and producing content for my clients in order to get paid.


They don’t dictate that I work certain hours, but I do have deadlines on certain days. Plus, that combined with the fact that my friends and family work traditional M-F 8-5 schedules means that’s pretty much when I work too.

When I first became self-employed, I imaged that I’d have time to go to the grocery store in the middle of the day, clean my house, workout, and more.

But, the truth is, I tend to still do most of those things outside of normal working hours – in the evenings and weekends. Plus, I usually end up working more than 40 hours week because of #1 and #2.

4. Diversifying Income Helps With Slow Times

A big lesson I’ve learned from self-employment is that diversifying your income can help a lot with the traditionally slow times of year. For me, that tends to be during the summer.

To combat this, I’ve built my business to have lots of different types of work to help ensure my paycheck is as “steady” as possible. My bread and  butter is freelance writing and blog management/Virtual Assistant work.

But, I’m building the income stream I earn from my own blog, too. This includes income from advertising, partnering with brands, affiliate marketing, and I plan to create and launch a course soon. I’ve also started a coaching program to help people up-level their freelance writing and Virtual Assistant businesses.

Find out more about my coaching program here.

5. Networking is Key

Building relationships with people in my niche has been a game-changer for my business. Knowing the right people helped me grow my business quickly off of referrals. Without those, I wouldn’t have been able to fully replace my day job’s income and quit my job only 12 months after I started freelancing!

Looking back on that, it’s amazing I was able to do that so quickly. It felt like it was slow going, but now I realize my business was actually growing very quickly.

Networking has helped me gain new, higher-paying clients. Plus, it’s given me an audience to go to with questions and for support when I need it.

Even though I consider myself mostly a solopreneur, it’s nice to have a network of other people in the same general field so we can all support each other. I also know I’m lucky because not all niche’s are as supportive as the personal finance community. 🙂

6. It’s Ok to Pivot

Finally, I’ve learned that it’s ok to pivot and make changes to your business. Although I started out making 100% of my income from freelance writing and Virtual Assistant work, I’m now working on making a pivot away from so much of those types of projects.

I am trying to build my community on Facebook and my email newsletter. This way I can connect more closely with those of you who’ve been here since I started back in 2013.

Pivoting is a natural way to change your business as your needs and interests change. Plus, it’s not a bad thing to switch things up now and then.

Why Are These Self-Employment Lessons So Negative?

I like to paint a realistic picture of what self-employment looks like, at least for me.

I don’t want you to think that being self-employed is all about sitting by the pool, jet-setting on vacations, and working 5 hours/week to make 5 figures/month. That is absolutely not realistic for most self-employed people.

Unfortunately, I think too many of us who are self-employed make it seem easier or more luxurious than it is by sharing only the best parts of our lives on social media.

If you ever decide to pursue self-employment, I want you to know that it’s going to be hard. It’s not glamorous most of the time either.

Most days I barely have time to brush my hair and prepare healthy-ish meals. I work my a$$ off to succeed, because I don’t have (much of) a safety net. And I’ll be damned if I’m going to fail because I didn’t work hard enough. #toughlove

What’s Next?

As I kind of alluded to, I’m hoping to make some changes to my business during year three.

I’ve opened up 5 spots for new coaching students. Plus, I plan to pass on some of my current clients, and future job requests to my coaching students. This should help me free up some time. Then, I can focus more on coaching, creating my course, and building this website and community instead of only freelancing.

I feel like it’s a natural pivot for my business. After all, I didn’t quit my job to help make other people’s businesses succeed.

I quit my job to be my own business and help my business succeed. I feel like I’m kind of capped out at what I can do with spreading my own message and building my own business unless I make a change to focus on less freelancing work.

If you’re interested in my coaching program or the up-coming course, drop your email below to get updates and exclusive content from me:



  • Everything you said here has been completely true in my experience as well. There’s a huge difference between simply working from home and working for yourself (regardless of location). I think not having any benefits is probably the biggest negative since it causes so much pressure to continue working and earning to cover everything that would have been paid by an employer.

    I’m glad you mentioned pivoting, though. So many people stick with what they started doing because they don’t allow themselves the time to reflect on where they (and their business) should be heading. And as we all know, that just leads to burning out. Can’t wait to see what happens when you put your business first!

    • I agree! Not having benefits is a huge downside to being self-employed. But, I still prefer it over working for someone else. If I were to ever go back to working for someone else, it would have to be an amazing fit and great offer.

      Pivoting and changing direction can be so hard! I think people sometimes think that changing what they offer or what they do in their business is kind of like admitting failure. But, I disagree! I’ve definitely been successful with freelancing (in my opinion, haha). It’s just time for a change! Change is hard, but so good!

  • Kayla, I’m so excited for you! I’m not at the point where I’m ready to take things to the next level but maybe one day in the future. Congratulations on setting strong goals and really going for what you want. I’m looking forward to seeing all the changes in the coming year.

    • Thank you! I hope that you continue to be inspired and achieve your goals! Stay motivated!

  • Loved this Kayla! As someone who’s just starting out on the self-employed path, it was great to get a snapshot of what it’s been like for you – AND that you started out with debt. This is where I’m at. I also struggled with the idea of what services to offer and realized that I need to just offer something and then pivot or add/subtract.
    Thanks for sharing this and wishing you more success!!

    • Thanks Michelle! I totally get that. I think the key is to just get started with SOMETHING. You can always change your business offerings over time. 🙂

  • Loved this post Kayla! Thanks for painting a real picture for a newbie like me!! I definitely see what you mean by pivoting! I’m sure it may be hard to go out of your comfort zone, but you’ll never know unless you try! I’m so thankful you’ve help my little business along and you’re one that I definitely look up to!

    • Aww! Thank you Gretchen. I’m so happy to be connected with you and I can’t wait to see your business succeed over the long-term. 🙂


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