Thinking of Being Your Own Boss? Here’s 10 Ways to Ease the Transition

On October 10th I hit my 6-month “being your own boss” milestone.

“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?”

Well for two reasons: 1) because it's my blog and I'll cry do what I want to.

And 2) 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. 

You see….

Moving to NYC with no money also taught me a great deal, but that was five years ago.  So I guess it's been five years since I really, truly stretched myself by doing something even I didn't think was possible.

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.


1. Being Your Own Boss – The Initial “Leap” Is Actually the Easiest Part

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.

2. Processes Aren't All Bad

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. I struggled a good bit with adding “legitimacy” to my business and managing the expectations of my clients when I swapped from side hustler to FT #girlboss. (I wrote about it in this post, here.) Processes were a huge part of making that shift, and it took me longer than it should have to realize it.

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.

3. You're Gonna Have to Grow a Backbone….Like, a Real One.

I love all of the items on this list, but I feel #3 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 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/clarifying a point in an agreement didn't make me difficult. It just makes me a business owner.

RELATED: 40 Pieces of Advice from Real Girl Bosses

4. Disregard Authority Figures. You are the Ultimate Authority Figure of Your Business

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. I'm NOT recommending you go ham on someone or disregard authority just for the sake of doing so, but I know for me, 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 it's important to keep them happy.

But a big part in standing up for yourself 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.

I was crying on the phone to my Mom after a particularly hard and stressful work day a few months back, agonizing over a decision.
“Lauren,” she said, incredulous I was even upset, “You work for yourself. Give yourself permission to do what you want to do.”

And I realized that she's right.

Give yourself permission has become one of my daily mantras because it works both in business and my personal life.

Giving yourself permission to do the things you want to do, without waiting on someone else to give you the keys to your happiness.

5. It's Stressful (but worth it)

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 (even if you outsource important parts of it, and I'll get to that later) 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, “Lean into the curve.”

RELATED: How to Deal with Sneaky Money Stress

6. You Have to Prioritize Your Own Well-Being

If I had a dollar for every time I skipped a workout or yoga class because I was caught up in something or wanted to accommodate a clients 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 also (foolishly) 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.

7. You'll Discover How You Work Best

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 on literally everything.

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 mingle 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.

8. Accounts Receivable Will Always Give You the Heebs….but the Money Means More

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. That's pretty badass!”

Also, keep in mind that when you are your own boss your earning potential isn't capped like it is in someone else's business. I think this was one of the most important reasons I left my full-time job; I knew I could be making more if I went out on my own.

9. Who You Surround Yourself With Is Crucial

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're out running 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 bigger and better things.

10. Boundaries Will Bleed Together

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 bleed. Shutting off for a few hours each day is something I'm continuously getting better at, but 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.


10 of the most important things you'll learn during the first few months of being your own boss. It's amazing and terrifying all at the same time.


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  • MakintheBacon
    November 6, 2015 at 8:22 am

    I love hearing the lessons and the experiences that people go through when they are their own boss. The more I hear about it, the more I get curious and wonder if I should try making that leap in the near future (meaning in a few years). Making a recent career switch was the biggest leap for me thus far and I couldn’t be more happier. Who knows what leap I’ll take next? 🙂

  • tbaxter
    October 21, 2015 at 10:13 pm

    I’m looking forward to reading your post. Unfortunately, the type is so light and lacking in contrast it was too hard to read online, so I have to copy it into a Word doc to read it. If you’d like help with correcting this problem, I design web sites and would be happy to lend a free hand. 🙂

    • Lauren Bee
      October 22, 2015 at 6:44 pm

      oh no! I appreciate the feedback. feel free to email me.

  • Christina Scalera
    October 21, 2015 at 12:30 pm

    Thanks for the honesty Lauren! It’s nice to feel like I’m not alone.

    • Lauren Bee
      October 22, 2015 at 6:44 pm

      No one is out there alone, and I am so looking forward to seeing you next week. I go out of town and you start three new businesses 😉

  • Emily @ evolvingPF
    October 20, 2015 at 9:36 pm

    Thanks for sharing these thoughts! I have had many similar revelations over the past few months, though have probably taken less action than you have. I also was very surprised to find that I wasn’t working out regularly, like, automatically. I need to be more conscious about making that part of my daily/weekly schedule. For the most part I enjoy not having firm boundaries between professional and personal time. I took a long weekend away from work last month and it was very difficult to both tear myself away and get back into the swing of things. I miss my work when I put it down for too long (in a good way)!

    • Lauren Bee
      October 22, 2015 at 6:45 pm

      Yes, it’s your “baby” so the time you spend with it means more for sure. I get that. I don’t mind the bleed, but I do worry about letting it run away with my life.

  • Giulia Lombardo
    October 20, 2015 at 11:25 am

    Great lessons and alls very encouraging for someone that would like to be boss of myself but I still haven’t courage to do it, maybe between 10 years for the moment I’m following my real estate passion as realtors…however thanks for sharing!!!

    • Lauren Bee
      October 22, 2015 at 6:45 pm

      You’re welcome- thanks Giulia!

  • Money Beagle
    October 20, 2015 at 9:22 am

    Good for you, sounds like you’ve come a long way fast. Look forward to continuing to read about the successes and challenges that will come your way as you continue to move ahead.

    • Lauren Bee
      October 22, 2015 at 6:45 pm

      Thanks MB!

  • Dia
    October 19, 2015 at 11:36 pm

    Happy anniversary! These are all great lessons and I’m taking notes for when I get there. I do worry about the time management part because even as I write this it’s 30 minutes past the time I told myself I’d shut down the computer for the night. Sometimes I’ll get so into what I’m writing or trying to network or find inspiration I get caught up and don’t balance well. But I’m working on it. Thanks for sharing your experience.

    • Lauren Bee
      October 22, 2015 at 6:45 pm

      You’re welcome, Dia! Thanks for checking in. Let me know if I can ever lend a hand.

  • Cat Alford/ Budget Blonde
    October 19, 2015 at 4:49 pm

    I love this post! These are all great lessons that I experienced too when I went full-time with my business. Thanks for sharing them!

    • Lauren Bee
      October 22, 2015 at 6:46 pm

      Glad you took a moment from your busy day to read Ms. TV star!

  • Stefanie @ brokeandbeau
    October 19, 2015 at 12:48 pm

    The timeline for getting paid as a freelancer is ridiculous. I now plan my budget only around payments RECEIVED the previous month, not work done. That way I’m not spending with income that hasn’t come in yet. A lot of great lessons here. Happy anniversary!

    • Lauren Bee
      October 22, 2015 at 6:46 pm

      Thanks for that tip- I should definitely start doing that. Grrrr.