5 Lessons Learned After 2 Years of Self-Employment

Yes, It’s been two years already that I’ve been working for myself. My first day of self-employment was September 1st, 2016 and it seems like it was just yesterday.

I never thought I’d quit my job to start working for myself, but I never felt like I fit in at other jobs. I never felt like working for someone else was the right fit for me. I started my blog in December 2014 on a whim. It was either a personal finance blog or a resume writing blog and business. Did I ever openly share that? I didn’t think so.

Needless to say, this little blog was one of the best things that ever happened to me. In unlocked a new passion and purpose along with a more fulfilling lifestyle and career.

It hasn’t been all roses and unicorns, however. Here are 5 lessons about self-employment that I learned in the past two years.

1. Working For Yourself Isn’t the Key to Happiness

I find it hard to convince myself that I fun a small business. Sure, I freelance and some people may say that’s not a business, but it basically is. It requires so much work just to stay on top of everything. Plus, I manage a small team to help run me this blog which I treat like a business.

There’s this big push for people (especially millennials) to chase their dreams and start a business. We see people sharing their best highlights of entrepreneurship on Instagram. I can’t go on Facebook without seeing an ad from a successful “guru” who is offering a free training to do this and that.

They all promise or imply the same thing: that you will be happy, fulfilled, and experience true freedom when you take the leap from your boring and mediocre 9 to 5.

This isn’t necessarily true so don’t get your hopes up if you’re considering full-time self-employment. In the past 2 years, working for myself has only made me about 25% happier overall.

That happiness stems from the fact that I no longer feel anxiety on Sunday nights because I don’t have to drive to a job I hate in the morning, along with being able to do meaningful work that I love and the ability to be more present in my son’s life.

I can take field trips with him, pick him up from school each day, and spend more time with him now that I set my own hours.

However, I still work and I still have bad days just as often as the good days. Entrepreneurship won’t bring total and complete happiness in your life. If that were the case, successful business owners wouldn’t be identifying with depression and heads of big brands wouldn’t commit suicide, unfortunately. Money and the freedom having a business provide doesn’t solve all your problems.

Happiness is a choice, and it’s already inside of you. Last year, I read The Happiness Dare which has some spiritual elements to it, but it’s a must-read for anyone who’s trying to consciously focus on improving their level of happiness.

2. It Can Get Lonelyyyyyyyy

Being able to work at home in my pajamas is wonderful, but it can get lonely. After two years, I don’t miss office politics, but I do miss interacting with more people on a regular basis.

It’s so easy to get caught up with work and talking to my online entrepreneur friends that I forget the whole day has almost passed and I haven’t even left the house. Sometimes, my saving grace is knowing that I have to pick my son up from school.

About a year ago, I started a meetup group for local bloggers, but it was more like a mastermind and it was difficult to get a consistent schedule and attendance.

Now, I know I just need to focus on getting out and being around people more often. If you’re self-employed, you need to try coworking, meetups, or simply hold yourself accountable for taking the time to hang out with friends, and other people. Don’t let deadlines run your life. There will always be something to do in your business.

I will probably be trying another coworking space in the near future.

3. Time is Money

If you want to become self-employed and be successful at it, you’ll need to become great at time management. Time is money but this is especially true when you start working for yourself.

If I don’t work, I don’t get paid. It’s up to me to generate streams of income to keep my business afloat. When I want to take time off, I need to make sure I’m still meeting my minimum income requirements.

There’s no one to monitor me to make sure I get a certain amount of work done or stay on track. This puts more pressure on my to focus and be productive.

I’m not going to lie, sometimes I fail at this and have super unproductive days.

I often view my success in terms of time. I’ve learned to cut out distractions, set working hours and say no to requests that occur during those hours. Just because I’m in control of my own schedule doesn’t mean I can drop what I’m doing at 11 am and run an errand for a family member.

I thrive when working during mornings and daytime hours so I now know that lost focus and lost time often translates into lost money.

4. Set Your Income Goals High to Create Consistency

I’m sure everyone wants to make more money when they transition from 9-5 to self-employment. I’ve read income reports before where people talked about wanting to make HUGE amounts of money. Now, from one perspective, that may make them seem greedy, but I totally get it.

When you work for yourself, you basically have to make more money than you think you need. There are tons of expenses you may have to cover to keep your business running. Plus, taxes are higher and you’ll need to cover your own benefits like health insurance, retirement, and time off.

Since your expenses will likely increase, your income needs to increase right along with it. It sounds crazy, but for someone who’s self-employed and has a family, $8,000 a month ($96,000 per year) may or may not be a sustainable enough income.

If you set aside around 25% of your earnings for taxes, that’s $2,000 you’d need to put away. Then, say your business expenses are around $1,000 per month. That already brings you down to $5,000 total profit. If your rent or mortgage is $1,500 per month, that leaves you with $3,500 left. You see how it goes from there.

Also, it’s important not to forget that your income will fluctuate all the time when working for yourself. To keep things consistent, it helps to set your income goals high so you can save some of the surplus for slower months. I’ve gone without having a checking account buffer or savings stash and it can be stressful when my monthly earnings come in lower than expected.

Related: Why I Left a Stable Paycheck For an Uncertain Income

5. Narrowing Down Your Niche Is Important

When I started playing around with the idea of becoming self-employed, I just wanted to make money and prove to myself that it was possible. I said yes to everything and tried to serve anyone and every with this blog.

It took a long time, but I finally came to the realization that I need to niche down in order to reach my long-term business goals.

I just came back from a conference last month and that was the most important lesson I learned there. I stumbled over my pitch when meeting others and eventually realized that I just sounded confused and generic. I knew that after blogging for almost 4 years, that shouldn’t be the case.

It sucks that it took me years to realize that, but now that I know, I’m looking forward to niching down with this site and my freelance work.

If you are thinking of becoming self-employed, choose a specific niche or two that you want to focus on. You may think this will limit your capabilities, but it will actually do the opposite. When you are clear on who you serve, you can start to become an expert in your field and offer more value to your target audience.

Those are just 5 of the key lessons about self-employment that I’ve learned in the past 2 years.

Did any of these things surprise you? If you’re self-employed, did you also find some of these lessons to be true?


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