Dos and Don’ts of being your own boss


Kelsey Cruz

Kelsey Cruz

Blog author Kelsey Cruz

Kelsey Cruz is a feminist blogger from the city of brotherly love who is obsessed with bourbon, black blazers, and blow-out bars. She loves to cook and is always up to swap smoothie recipes. Mostly, though, she likes long walks on the Philly streets with her pit-boxer Henry of whom she will definitely show you pictures. Follow her on Twitter @kelsey_cruz.

Published March 3, 2016|8 min read

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Ever since I was a little girl, I’ve loved reading and writing. I read all day, scored so much pizza from those Pizza Hut BOOK IT! programs (remember those?!), and filled countless journals and Xangas with quotes I loved and feelings I felt. I always knew I wanted to write, and I joined every English class, journalism program, and college newsroom to further my dream of becoming a writer.Yet, sadly, as I grew older, everyone became a "writer" and the journalism job market grew slimmer and harder to infiltrate (not to mention the dismal salary most magazines and newspapers pay their journalists is unlivable). Needing to eat and have a home, I decided to start working full-time at other jobs to make a living and put my writing on the back burner. And in doing so, I learned a lot: I learned how to work with various personalities, be effective and efficient, do presentations, speak up in meetings, carry on personal and professional conversations with colleagues and clients, and trust my instincts. I enjoy working in an office, and I strive to be a fantastic employee and learn from those who manage me.But if you’re tired of answering to someone and want to quit your job and take what you’ve learned to work for yourself, you need to first make sure you’re ready. More than ever, Americans are working for themselves – 15 million people, in fact – and it’s on the rise. So if you want to be one of them, let’s look at some DOs and DON’Ts of running your own business.

You’re ready to be your own boss if you DO

Thrive under stress. Abby Speicher, CEO and co-founder of DARTdrones Flight School, says owning your own company is stressful and that in order to be a successful entrepreneur, you need to be able to work under pressure, not collapse from it. If you do well in stressful situations and work effectively and efficiently through high demands, being your own boss will be a great path, but if you lose energy and panic under pressure, you will quickly realize owning your own company can be burdensome to yourself and those around you.Understand technology. Gone are the days of storefronts, office spaces, and mall carts because while you can still use those to sell products and run a business, technology helps entrepreneurs run startup businesses from their homes and laptops. Aaron Zwas, consultant and author of Transition to Independence, says he doesn’t need a physical store, inventory or employees to run his company. In fact, his annual costs of running a consultancy from his home range from $2,000 to $5,000 annually. And if you do run across a project you don’t know how to do, whether it’s website design or social media navigation, you can hire someone to do it for you or teach you how.Have and prioritize clients. "Don’t even think of starting without locking down paying customers," says Ken Greenberg, founder and president of consulting firm Edge Communications, Inc. If you want to leave your job and work for yourself but don’t have the clients or experience to do so, you need to press the brakes. And I’m sure you’ve heard that the customer is always right, and while I don’t necessarily believe that’s true (I was a waitress for almost ten years, and there were many, many incorrect customers), I believe every business – no matter how big or small – is about the customers and making them feel important and valued, regardless if they’re right or wrong. When you think about your clients and demographics in every facet of your business plan and make them a priority – how they’ll feel, what they’ll think, how they’ll react – everything else will fall into place.

Have money. My major 2016 goal is to make better financial decisions, and I try my best to save more and budget better to make the most of my income and what I can do with it. If you quit your job and start your company with nothing in your bank account, you will only be setting yourself up to fail so make sure you have ample funds to start working for yourself. You may not make much or any type of profit for a while so make sure you have enough money to survive for at least six months. What’s more, if you have wonderful benefits like health insurance, a 401(k), and paid time off with your full-time job, those are trickier (and sometimes more costly) to come by when you’re self-employed.Your research. Know your product or service, demographic, and market and know how to get insurance and how to file taxes. Know the ins and outs of being a small business owner and make a checklist of everything you’ll need – physically, financially, mentally, and emotionally – to make your startup business work and grow. Make sure you know everything about your business and how to make it successful. Once you know WHY you want to be an entrepreneur, create smart, clear goals and plans to finalize the HOWs, WHATs, WHEREs, and WHENs.Set boundaries. "When you work for yourself, often even the most well-meaning people in your life think it means you are available anytime," says Phyllis Nichols, founder and CEO of SoundAdvice Sales and Marketing. Being an entrepreneur means setting your own expectations, schedule, and deadlines, so if you miss a soccer game or night out with friends, it’s harder to explain to those you love because you don’t have a boss to blame for your absence. By setting boundaries from the start – non-negotiable work hours or time for client calls – and sticking to them will help make your work-life balance easier.Take charge. "It is often said that the true test of a business and its leader is how they deal with tricky situations," writes James Caan in the Guardian. "When you are working for somebody else you don't have the same responsibilities, but as the boss you have to become the problem solver. It's easy to point fingers or complain in business, but as the owner you have to take charge." When I worked in restaurants, I watched my managers take the brunt of every annoyed customer even if they had nothing to do with the problem. Why? Because managers, CEOs, team leads, and supervisors are the bosses, and they represent the organization and brand. If a client is upset with her order or service, someone needs to hear about it and that someone is the person in charge. Bosses take fault, apologize, grovel, and make things right. So if you cower at confrontation and can’t handle being yelled at, you’re probably not ready to run your own company.

You’re ready to be your own boss if you DON’T

Overextend yourself. Greenberg says it’s important to set realistic expectations, no matter how prepared you are to run your business. "A colleague started a conventional PR firm – with office space, employees, and a lot of other overhead – about when I did," he explains. "He was talented, but the costs of the model proved insurmountable and he closed after less than two years." If you anticipate too much too soon – a lot of clients, profit, and office space – your ego and bank account will take a hit. Set your bar at a reasonable height so you can effectively meet the needs and demands of your market and budget.Seek power. Yes, if you’re the boss, you have power and authority, but don’t beat your employees over the head with it. Instead of power, seek achievement and success by demonstrating good ethics, decision-making, and relationships, not by bullying or strutting. In an article for, Steve Toback writes, "You want to go places, but on your own merits, not by bullying or pushing people around. You want to make good money, but by contributing to the growth and success of the business, not because you feel entitled to it in some way. You don't want things handed to you; you want to be challenged."Fear taking risks. Quitting your job and working for yourself is a scary thing, but fear is palpable, and if you’re afraid, it will be obvious to your friends, family, investors, and clients. Be bold and brave and always remember why you took the risk of being an entrepreneur and what your successful business means to yourself and your family. And if you want to be afraid, be afraid of not trying and committing because not giving your business and self a chance – when you’ve dotted all your I’s and crossed all your T’s and know you’re truly ready – is the biggest mistake you can make.There are countless other tips and tricks to being your own boss and running your own business, but you’re the most knowledgeable about yourself and what you can handle. If you feel you’re ready to be your own boss, congratulations and best of luck! But if you need some more time to research and set goals and budgets, be my guest. The important thing is that you’re starting the process and thinking it through with the right mindset – positively, realistically, and intellectually.