10 Things I Learned From Being My Own Boss

On October 10th, I hit my six-month milestone of being self employed. "Lauren, you crazy," you'll say, "Why are you celebrating six months and writing about it? Shouldn't you wait until at least a year has gone by?"

I think it's because deep down I always had the anxiety that I wouldn't make it this far, that I'd fold within the first month or 90 days. But more than that I wanted to celebrate this small milestone because I've already learned more about who I am as a person, (and you know...business stuff) in the last six months than I have in my entire life.

My friend Paula shared this little nugget of wisdom with me when I was about to leave my job. "Time flies once you stop watching the minutes count down on the clock in your cubicle," she said. "It's all going to go so quickly."

And boy was she right. Time has flown so quickly that it's thrilling and a little bit scary all at once. Perhaps this is why I wanted to pause at the six month mark and write it all down: out of fear I'd blink and miss it if I didn't. So, I want to add to Paula's wisdom by sharing 10 important lessons I've learned from being my own boss.


I tossed around the idea of making the switch from side hustler to full time solopreneur for years. Whenever I thought about it, it never seemed like quite the right time. Finally my bandwidth got so maxed out I had to make a decision: pull the trigger on working for myself, or let some clients go.

Maybe it's the fact that once you do, in fact, become your own boss you're thrown into a chaotic mess of to-dos that need to get finished and don't have time to think about what you're doing.

But making the leap, actually putting the plan in place and acting on it?

It's been the easiest part of my journey so far.

So for all of you contemplating making a switch of your own, my advice is to save your pennies and just do it.


I was working with another contractor on an email campaign for a shared client of ours, and our weekly calls with the client would become so annoying I started to dread the call. During the call the other contractor would reference some process document, and if we didn't have one, she'd take time out of the meeting to discuss and brainstorm creating...wait for it...another process document.

Every time she would do this, I would roll my eyes and think, "processes are for corporates. We don't need that here."

But after a few months I realized maybe there was a nugget of truth in her crazy extreme- processes aren't all bad, they exist for a reason. Even if it's as simple as having a formal on-boarding process or "what to expect document," those constructs let clients and customers know you mean business.


I love all of the items on this list, but I feel number three is most important for bosses everywhere. It's certainly the area where I feel most empowered and proud of my personal growth.

I wouldn't say I'm one to shy away from conflict, but sometimes the "eager to please" part of my personality kicks in, especially when money gets involved. In the last six months I've found myself in projects or commitments that aren't always to my benefit, the best use of my time, or at the level of compensation I'd like.

It's a learning curve, but eventually you'll realize that being easygoing all the time is taking a cut out of your bottom line.

I know, it sucks at first when you realize that there there is literally NO ONE else to have those tough conversations like there was at your old job. This is where the grit of being your own boss comes in. You can go crying back to corporate if you want... it's definitely nice there sometimes.

But if you want to be your own boss, you have to grow a backbone. Not a fake one. A real one.

I thought the world would implode if I "made someone mad at me." Trust me, it doesn't. I also realized that me questioning something, or double checking and clarifying a point in an agreement, didn't make me difficult. It just makes me a business owner.


We're all raised with a healthy fear of authority. After all, it's how we get through school, receive an education and become functioning members of society. For the first few months of being my own boss, I was treating my clients like they were still a "boss" of some sort or an authority figure in my life.

Sure, clients are important. They butter your bread and pay your bills and its important to keep them happy. But a big part in standing up for yourself (see number three) comes with realizing that there are no longer any authority figures in your work life.

It's just you, and you get to set the rules.


After working full time for an employer, writing this blog, and hustling on the side for clients for over three years I (foolishly) thought that working for myself would be a step back in a lot of ways: more free time + less expectations = less stress, right?

Nope. Nope. Nope.

Being your own boss is stressful (sorry, it just is. I'm not going to candy coat it for you.) This is mostly because every aspect of your business is all on you. All of it. 100%. It's sink or swim. Feast or Famine.

But that's not to say the stress won't lessen over time, or that the struggle isn't worth it. I've had some of the most stressful weeks of my life since becoming my own boss, but I do know that I've never been as challenged, engaged, or in love with my career.

Stress is just a part of it. Own it. Or as my fictional BFF Mindy Kaling says in her latest book, "Lean into the curve."


If I had a dollar for every time I skipped a workout or yoga class because I was caught up in an article or wanted to accommodate a client's request for a phone call, I probably could retire. Finally, after weeks of feeling gross and stressed out, I began carving out time to walk my dog for 40 minutes each day and attend a yoga class three times a week.

I thought that working for myself meant I'd automatically have more time for daily yoga class and working on a hot summer bod. I mean, I work for myself and dictate my own schedule every single day. Exercising, meal planning and doctor's visits should be no problem, right?

Except it's not as easy as all that. Just like when you worked a 9-5, you'll have to schedule in time for yourself. It's even more important because your business depends on your well being, but also important because wellness will never work for a solopreneur unless you set some boundaries.


Perhaps the biggest surprise of all in my short six month journey is how horrible I am at working from home.

This was a shocking revelation because I've dreamed (pretty much since I graduated college) about being the type of writer who works from home in her PJ's, netflix on in the background, simultaneously doing laundry and knocking out client projects one-by-one. It would be quiet and still and I'd write the most amazing blog posts of my life and never have to fight Atlanta traffic again.

And I was that writer for the first three months I worked for myself. But she wasn't glamorous and productive-she was easily distracted, disorganized and behind from the moment she woke up.

So I tested out working from coffee shops and eventually found my way to a co-working space. And I realized that I actually like getting out of the house, having a place to go where I can focus, and even mingling with a few folks from time to time.

"Lauren, you've worked so hard to break free of an office with fluorescent lighting and coffee pot small talk," my psyche thought, "Why are you willingly paying for an office again?"

Because that's just how I work best. It's business-y self discovery and that's okay, too.


Ask any solopreneur or small business owner what their biggest issue is and I guarantee "bringing in the money," is somewhere near the top of the list. Eventually your processes become more streamlined and efficient, or you may outsource bookkeeping and invoicing to someone else, but there will always be the clients who take forever to pay you, kick up a fuss when you want a 50% deposit, or (and I guarantee this will happen at some point in your career) not pay you at all.

If you weren't comfortable with those tough money conversations before, you will be after becoming your own boss. They'll never be a breeze 100% of the time, but it does get easier.

And another thing that's important to note here is how the money I'm making means more to me now. It's different when someone else hands you that paycheck, but at the end of every month I look at the uptick in my business income and think, "hey! I made [x] amount this month on my own. All by myself! That's pretty bada*s!"


We're all familiar with the old, "you are you hang out with" cliche. Whether or not you believe there is any truth to it, your networks become even more vital when you run your own business. Sure, networking is a great way to socialize and meet new folks who can (hopefully) bring you new clients, but networking with other entrepreneurs has been one of the most invaluable keys to my (albeit small) success these last few months.

From Kenzie, my beautiful client who has mentored the crap out of me to several group mind shares and masterminds I'm a part of on Facebook, these groups have allowed me to vent, ask questions about something I'm working through, and most importantly, learn from others who traveled the road ahead.

It's important to surround yourself with good allies, team members and contractors as well. This will free you up to do the bigger and better things you left your job for in the first place.


One of my favorite quotes about business owners and entrepreneurs is this: "I'd rather hustle 24/7 than work 9-5."

Work-life balance is crucial at any point in your career, but it can be elusive once you become your own boss (see point #5 above.) Especially in the beginning when you're working to get something off the ground and into flight. I've taken breaks and vacations in the last six months, but I've never been able to completely leave my business behind or drop work at the door come 5:00.

Okay, as a blogger-hustler I've never quite been able to do this, but as my own boss the boundaries between work and life continue to persistently bleed. Rather than let it stress me out I choose instead to embrace this mess.

After all, nothing worthwhile ever comes easy, and I know the mess is enabling me to work toward a far greater reward than I'd ever get working for someone else's business or cause.