20 Lessons You’ll Learn When You Become Self Employed

On April 10th 2016 I celebrated being in business for myself for one year. I wanted to do a post to commemorate the occasion, but then life hit and I got behind on what I had to do for clients and the milestone passed without much fanfare. Waiting awhile to celebrate has allowed me the opportunity to really sit and think about this past year, everything I’ve learned, and what it’s meant.If you take the 6 month, “10 Things I Learned Post” and add it to this one that’s 30 (!!!) things I’ve learned in one year.And these are just the highlights.

But the long and short of it all is this: I’ve never learned more this year than in any other of my entire life. Being your own boss is many, many things and so I tried to put it all down on paper, but probably did a terrible job 🙂

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Being Your Own Boss Requires Absolute Clarity

#1 – Clarity is Crucial

When you’re not the boss, you don’t have to think about things as much. That’s why bosses get paid the big bucks; it is their job to provide clarity, which can often be the hardest thing to find. You can run a business you’re unclear about, and even make money doing it…but you’ll never thrive unless you know – 100%– what it is you’re doing, selling, who you’re selling to, and why.

#2 – It’s Totally Different From Running a Side Business

I kind of fell into being my own boss when I ramped up my “side hustle” during the 8k in 90 day challenge. You can totally take your side hustle or side business and turn it into a full-time endeavor (that is often the goal of setting up a side biz in the first place!), but running one is completely different from running the other.

Admittedly, I was a little naïve on this point. You have to treat a full-time business differently than you do a side one, there’s just more moving parts.

#3 – There are Ebbs and Flows

When I first started, it never occurred to me that with digital marketing and content there could be “busy” and “slow” seasons just like any other business.

“People want to read new content all the time!,” I thought.


Every business has ebbs and flows, peaks and valleys. Running a business (and you know, preserving your own mental sanity) gets so much easier when you are able to tell when those times are.

 #4 – Saving Up Enough is SO Important

I wrote in this article for Grow that one of the biggest mistakes I made was not giving myself enough financial runway. Here’s why: your first year of business, you don’t know yet when your busy and slow seasons are yet (see above).

I wish I’d saved more money so I could’ve spared myself the nail biting time that was this post-December's dip in new business.

#5 – Listen to Your Creativity

In one of my “About L. Bee” personal essays, I talked about how I completely had to pivot my business this winter because I wasn’t feeling creative and inspired by what I was doing.

Sometimes it's when things are cloudy and confusing our creative impulses tell the largest truth.

By listening to mine (or rather, lack thereof) I was able to shift the business and work out something I felt much more pleased to run. If my new monthly income reports (read April and May) are any indication, it's been working out well—when it comes to both income and job satisfaction.

#6 –Articulate the “Why” Of It All

When things aren’t going well with your business, it’s important to remember the “Why.”

  • Why are you doing this?
  • What is all this hard work for?

If you can’t clearly articulate the “why” behind what you’re doing…well then, why do it?

When you become self-employed you'll have to be humble..

#7 – Nothing Prepares You

Over the last year I’ve had the chance to network with a lot of entrepreneurs.

Some are like me, who stumbled their way into it from some pretty unexpected places (hello, I used to be a working actor…) and others who went to fancy business schools and have MBA’s hanging on their walls.

One thing we all agree on? Nothing can prepare you for the reality of actually running a business.

#8 – Education is Key

If there is one thing I’ve been guilty of this year, it’s been not seeking out educational opportunities for myself so I can continue to learn and grow. I'd been a big ol' lazy bum.

Back in January/February when I was pivoting my business, I finally figured out what I wanted to do and why, but was still stumped on how to get there. This is when I committed to seeking out resources: blog posts, e-books, courses, meet-ups that could help me attain my goal.

Side bonus? It’s been a lot of fun learning. I forgot how fun it was to learn new shit.

#9 – Structure Isn’t All Bad

I wear a lot of polka dots and smile a good bit, so sometimes people are surprised to learn that there is a tiny anarchist inside of me that hates being told what I can and cannot do.

I also especially hate authority and people who take what modicum of it they have too seriously.

“When I start my business, I won’t have any of these bullshit process documents…and NO CONFERENCE CALLS.” I thought.

I was wrong. Processes and structure aren’t always bad and they actually do serve a purpose. Most importantly, they keep you from free floating into the abyss and from spending your entire days on the couch with Netflix.

#10 – No Job is Perfect

Big myth: Everyone who hates their job and works in a cubicle thinks what I get to do is a walk through mythical, magic unicorn land.

And don’t get me wrong, I love my business, but every job has parts of it you’re not going to like.

For example, chasing people down for money or those aforementioned conference calls.

I don’t want to paint with a broad brush, but I think a lot of millennials struggle with this one point: they seek that one, perfect job that’s full of all the things they love and devoid of all the things they hate.

But with every job, whether you’re an assistant getting coffee or a CEO calling the shots, you're going to have to do a few things you’re not going to like. (I know, I was surprised too.)

The trick is to find something where you get to do as little of that thing you hate as possible, and if you work hard enough, maybe one day you’ll become boss enough to get to outsource that awful stuff to someone else.

#11 –You’ll have to Use Your Analytical Mind

Maybe it’s a bit different for businesses where there are multiple people in a shop, but as a solopreneur, I have to wear all the hats. Most days are spent with me doing a deep dive into the data of running a website: my Google Analytics, Mailchimp conversion numbers, Click Thrus, etc. This has been a huge surprise to me.

It's definitely a part of my brain I didn't use much in previous jobs and if you'd told me as a high school senior that my job in ten years would be mostly data and analysis driven, I would've laughed, but my blog was experiencing zero growth until I began to learn both which questions to ask and where to look to answer them.

Data, baby.

#12 – It Will Take About a Year To Feel Normal

I've been honest about how I've floundered around a lot this year, and watched more TV than any normal human should. I've experimented with my routine and what I want my days to look like.

But somewhere around the one year mark I began feeling more at home and at peace with my routine and what my work life looks like now. I guess it just took a bit of time for the new normal to begin feeling like the normal-normal.

#13 – Managing Money Will Be an Ongoing Process

Running a personal finance site it's difficult to not write about money, although you may have noticed I haven't written much about my own personal finances this year.

That's because working for yourself makes managing them…well, a bit more complex.

I'm still trying to figure out the best way for me to budget and save with my new solopreneur income. It's a process, but I'm trying to be gentle with myself. Managing money after all, is a lifelong journey. 

But Being Your Own Boss Will Also Give You All the Feels

#14 – It Will Feel Amazing…

I don't like to brag because I realize what a privilege it is to get to work from home, be my own boss, AND do something that I love that fulfills me creatively. Being your own boss is like everyone says, it's amazing and freeing and the flexibility is incredible.

#15 – And Other Times Feel Like Shit

I wrote about this a lot in this post about the peaks and valleys of being an entrepreneur, but yeah…it's stressful and sometimes it doesn't feel very good.

And some days you wake up and feel like you're not getting anywhere at all. I never remember feeling that way when I worked in a cubicle. Mostly I was just staring at the wall wondering when I could go home.

On days when I want to pull my hair out, I find it's best to commit to educating myself, so I bury my head in a course or an e-book, so I feel like I'm doing something worthwhile.

#16 – Watch Your Emotional Bandwidth

If you're wearing all the hats and doing everything, then doesn't it make sense that when you don't feel good, your business doesn't do well?

It's true.

If you're going to be your own boss and want real success, you're going to have to limit distractions, energy drains, and things that pull on your emotional bandwidth. This includes friendships, relationships, toxic people, and stuff that just isn't worth it.

Before I worked for myself I used to loooooove superficial drama, but I had to grow up because honestly, now I don't have time for it.

Worrying if I'm going to survive or thrive with my business is real drama, and so there is little room for anything outside of that anymore.

#17 – Self Care is Crucial

I've been sick more times in the first year of working for myself than any other. My doctor recommended I start taking vitamins and a probiotic, and you should too.

Because when you run your own business, when you're down with sickness, heartbreak, whatever…everything goes down. I'm thankful I've been able to implement new streams of revenue, like digital products and affiliates that are more passive than writing for clients, but it still doesn't feel good when you need to stop and you can't because you're running things.

#18 – Surround Yourself with People who “Get It”

Sometimes I like hanging out with my Lady Boss friends because I can vent about things that others wouldn't understand. This is okay. It's my version of a close work friend. Having a support system is especially important when you work from home too and I doubt I would've survived the last twelve months without the people I've been lucky enough to network with.

#19 – Fake It Till You Make It WORKS

People respond positively to confidence, so the more effort I've put into projecting this aura, the more successful I've been. And suddenly because you're doing better, you feel better, and everything just comes together.

But if you don't have it to begin with, faking it works too.

#20 – It will Change You

Like any big experience, being your own boss will change you. And not in the “I Work from home and have a different routine way,” but as a person too.

I'm better at some things now (critical thinking, taking my emotions out of things..) and worse at others (remembering dates, places, etc. and being in large groups of people because I'm so used to being alone…) but I recognize that's also where I'm at in my journey right now.

In another year it will probably look completely different.



Running your own company is tough. Here are the 20 most important things I learned and that you'll learn being your own boss.

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  • Dia
    June 9, 2016 at 1:26 pm

    So happy for you Lauren. I really hope to be there one day. Your blog and example has taught me so much.

    • Lauren Bowling
      June 13, 2016 at 3:20 pm

      Dia, you are so sweet. Thank you!

  • Colin // RebelwithaPlan
    June 8, 2016 at 7:25 am

    “Surround yourself with people who get it” YES! It’s so much better when you have people around you that really understand the frustrations you have.

    The realization that nothing prepares you for running a business is a huge realization. No amount of business books, articles, and other things will fully prepare you. It’s both scary and sort of thrilling to realize that.

    • Lauren Bowling
      June 8, 2016 at 12:22 pm

      I think to run a business having the right type of personality for it is the most important part. And tenacity!

  • Julie @ Millennial Boss
    June 8, 2016 at 1:00 am

    Congrats on a successful first year! I idealize what it would be like to work for myself and it’s good to know that there are bad days when you’re working for yourself too! Level set expectations. 🙂

    • Lauren Bowling
      June 8, 2016 at 12:20 pm

      a) I don’t like to brag but b) I also want to keep it real. Working for yourself is amazing, but there are bad days too.

  • Cat Alford/ Budget Blonde
    June 7, 2016 at 6:43 pm

    I couldn’t agree more with these things. Congrats on your anniversary!