
During my first two years in business, I worked full-time at other jobs (school secretary at a Head Start for a bit, office manager at a construction company after that). I ran my business and met with clients on evenings after work, weekends and holidays. When I was first able to go full-time with my business, I was straight out giddy for months. I have a vivid memory of driving down a street in a neighborhood I lived in, smiling and giggling for no reason other than that I was finally out on my own. (And if an old school hip hop song came on during my giddy moments? Fuggetaboudit. Damn near lost my shit in a happy way.)
But as the years went by, I lost some of that excitement. The further away I got from working for someone else, the more I forgot how miserable that made me. (Nothing against anyone in particular–in fact, my construction company boss, Ralph, was incredibly good to me and I learned some business tips from him that I still use today.) You know when you get a new car/new apartment/new boyfriend and it’s so awesome at first three months later you have a ready-to-share list of annoying things about it? That happened to me, the excitement phase lasted a solid year or two.
I have always been grateful that I have my company and have maintained that I could never work for someone else again. The thought of someone else being in charge makes my skin feel clammy. But I think I sometimes get bogged down by the sheer amount of work to be done or the frustrations of running a business and that makes me temporarily forget how friggin’ good I have it.
But I haven’t totally forgotten how dope it is to be my own boss. Being a business owner has become a huge part of my identity. I feel lucky that I am able to be where I am today without some of the roadblocks other people have had to encounter. I don’t take this opportunity to be an entrepreneur lightly, and I work hard to make sure it keeps happening.

The written word is extremely powerful to me, so I want to do this post as a reminder to myself–and maybe other business owners who’ve been at it a while–that there are a lot of things to be grateful for in boss life. And if you’re in the Early Struggle Years of running a business–where money is tight and you don’t know if your business will even stay afloat–maybe you’ll find this helpful too. If you are not already at some of these points, they very well may be there for you, possibly even sooner than you expect.
You know I love a good list, so here goes.
Schedule Freedom. When it comes to my schedule, there are some commitments (weddings, commercials, events, classes I attend) that require me to be there at a certain time. But other commitments–makeup lessons, wedding trials, meetings, classes I teach–are partially dependent on when I want to do them. And what I call my “admin days”–days with no clients, meetings, classes or appointments–are completely up to me. Today is one of those. I got up when my body wanted to (7:30am) and have been working from bed. I’m leaving soon to walk to the bank (work-related), then I’ll go Staples (work-related), laundromat (personal) and grocery store (personal). When I get home, I’ll work until I decide I need a break, then I’ll go for a run. I often end my work day around 9:00pm, but my personal stuff is sprinkled in throughout the day. I’m very grateful that on my walk to the bank, I can stop in a store and pick up a birthday gift for a friend or take care of some other task on my personal To Do list. No one is breathing down my neck, timing my return to the office, ready to freak out on me because I walked in two minutes after my break ended. No one can tell me I can’t do what I want to do when I want to do it. Timing-wise, it’s not really work/life balance since I spend more time working than not working. However, it is a type of balance in the way that I don’t have to cram all of my personal errands and appointments into nights and weekends. This schedule freedom is one of my favorite parts of being an business owner, as you can see by the length of this paragraph.
Job Freedom. When I first started doing makeup, I wanted to be a freelance, one woman show. I thought I could work in film and maybe do some weddings on the side. I soon realized working in film wasn’t the right path for me, so I changed course. And that’s something else I am immensely grateful for–the freedom to choose the direction of my career. I don’t have to climb up the corporate ladder to get to where I want to be. I just decide, This is what I want to do, then I go for. It doesn’t always work out, but I’m at least able to try. This career freedom is something I take for granted until I hear someone talk about the constraints of the structure at their company and how they are not always able to work the job they want to be working. Creating my own job description and changing it when and how I want to is exactly what this little INFJ craves.

Working from Home. Not only do I get to decide when I work and what I work on, but on admin days (or partial admin days), where I do my work. In Rhode Island, I have a office where I meet with clients, but I normally work from home. In my current winter home in South Carolina, I sometimes work at the desk in my studio apartment or, like I’m doing right now, from my bed. (What? The desk chair is uncomfortable!) If I want to work from a coffee shop for a change of pace, I can do that too. Raining, snowing or cold out? Unless I have clients, I don’t have to leave my house to go to work. The convenience of it all is just too good. The freedom to choose my workplace in combination with my schedule freedom makes my job feel more like part of my life than a separate thing I have to go to at a place not of my choosing. When I hear friends say they had a nightmare three hour commute because of black ice but they had to go in anyway, or how their company requires them to go into an office every day even though 95% of their work can be done from anywhere with a computer and a phone, I am reminded of how lucky I am. I love that more and more companies are allowing telecommuting so even if you’re not a business owner, you can get some of this flexibility. It’s a game changer.
Ability to Change the Job. When you’re the captain of the ship, you can decide how you want to run it (or sail it? I don’t know). I’ve worked at jobs where I knew there was a better way to do something, but I couldn’t make changes because of rules, policies, prideful bosses, whatever. But with my company, no one can tell me I have to do something a certain way. When I started AB Beauty, I took what I didn’t like about the beauty industry and some small businesses in general and changed it within my company. Sure, there will always be laws and tax code I have to abide by, but I can create my own systems, style of management, methods of client communication, etc. This is something else I sometimes take for granted, because it is now so natural to me to change something if it’s causing problems. Again, I can’t always do that–and there are plenty of things I do that I don’t like because it makes things easier for my clients or Independent Contractors–but there is a lot I can change when I want to. And guess who I have to get permission from? NO ONE. It’s glorious.
Boss Pride. If you are doing a good job at whatever you do, I think you should be recognized for it, and I think you should be proud of your work. I have what some consider a harsh theory and it is this: 70% of people are bad at their jobs. I stand by that. When I have an interaction with someone who is doing a good job, I write a review, email their manager, leave a big tip–whatever. I think it’s rare for someone to be great at their job, so those 30-percenters deserve a thank you, a pat on the back and recognition. As a business owner, your company may win awards or be recognized in another way, but that doesn’t always happen. What you can do–and this is a hard one for me and I’m sure many other business owners–is be proud of the business you’ve created and the successes you’ve had. And at least in my experience, this pride feels different than the pride I felt when I got good performance reviews or raises when I worked for someone else. The boss pride is cool because you can say “I did this. I made this happen.” At my company, our success is in big part due to my team. I absolutely could not do it without them. So I hope they are proud too! But I do recognize that I played a part in each transaction that has ever happened at AB Beauty. I really feel like I worked for every penny that came in. There is no phoning it in as an entrepreneur (if you want to stay in business, anyway). Maybe this one seems weird to say, but I am grateful for the opportunity to feel proud of making a living for myself.
Friends & Family Time. You know that schedule freedom I talked about? That goes hand in hand with Friend & Family Time. If I want to make plans with a friend or relative and they can give me some notice, I can build my work day around them. For example, my parents came to visit me in SC recently. I can’t take a full day off, but I was able to do some work until noon, hang out with them all afternoon and into the evening, then catch up on work when I got home. I didn’t have to take personal time or play hooky so I could go on a Charleston carriage tour with them. I just got a lot of work done in the few days before they arrived to prep and then worked short, spread out hours on the days they were in town. I’ve said it before and I’ll say it again–being able to see my friends and family as much as possible was one of my two main personal goals when I opened my business. I still miss some things due to working weddings on spring, summer and fall weekends, but I’m grateful that this ladyboss gig gives me the schedule freedom to spend time with my friends and la famiglia.
Financial Freedom. On one hand, it is nice having consistent paychecks. For budgeting purposes, it’s so much easier to know exactly when you’ll get paid and how much your check will be. And a bad week at work for an employee doesn’t necessarily mean the same as a bad week for a business owner. An business owner’s bad week (or month…or quarter…or year) can mean severe financial stress and pressure. But a good week, month, quarter or year for a business owner? That can mean a bank account bump up you couldn’t get with six promotions at an employee job. There’s no income ceiling for bosses. My paychecks are the payments from my clients, and I can get more or bigger paychecks by booking more jobs, expanding the company, offering more services, etc. I have my ups and downs like any business owner, but I am thankful I have the chance to increase my income without a cap on my earning potential.
Charleston Snowbird. My second personal goal when I opened my business was to eventually be cold as little as possible, which means leaving New England during the winter. It took a long time, but I was able finally do it in 2017. I choose beautiful Charleston, SC as my (working) snowbird home and I LOVE IT HERE. It’s not tropical, but that’s okay. High 50s and 60s in the winter is fine with me (and it’s been even warmer than that lately). Unless I found an employee job that was a 100% telecommuting position, it’s unlikely that I would have had the chance to do this if I wasn’t a business owner. I mean, the only other people I know who winter somewhere warmer are retirees and people who work in the boating industry (and I get too seasick to even consider the latter as a career). Not only is the Charleston winter climate far superior to Rhode Island’s winter nightmare, but being here gives me the time to focus on my big picture business work, as I don’t really take clients here. It’s the perfect refresher and start to each year for me, and I am beyond grateful that my boss life allows me to do this.
A lot of the things I love about my life are due to my business. I feel very lucky that I’ve been able to create the lifestyle I want. When I’m feeling down or in a rough patch, this will be a good blog post to go back to. If you’re considering opening a business, these are some things you can look forward to potentially having at some point too. And if you’re already there, congratulations! It’s easier to quit than to push through, so if you’ve made it out the other side of the Early Struggle Years, props.
Have a beautiful day 🙂