Sick Of Working For Other People? Are You Wired To Be An Entrepreneur?

Sick of Working for Other People? Are You Wired to Be an Entrepreneur?

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Your boss is a jerk (and that's putting it nicely). Your commute sucks. Getting a 2% annual raise feels more like an insult than a reward.

In other words, you're getting fed up with being an employee, and you're starting to wonder whether it make sense to branch out on your own and start your own company. Be your own boss. Call the shots. BECOME THE MASTER OF YOUR OWN DESTINY!

The freedom of getting out of the workaday job, running your own company, and being an entrepreneur is a pretty sexy lure.

I made the transition myself in 2015 from corporate recruiter to running a resume writing and career coaching business – it's been fun, exciting, and rewarding.

But it's still a job. Which means that there's still work to be done. At the end of the day, the goal is to provide value to customers, translating this into a paycheck.

If you're thinking about making the transition from employee to self-employed, it's important to approach your thinking as if you are considering a career move. Because you are considering a career move - one in which you are the company.

Here are some factors to consider if you're considering a shift toward becoming your own employer.


  • Flexibility. You call the shots. Rather spend the day playing tiddlywinks or swigging down Guinness? No problem. You don't even need to call in sick while faking a hacking cough - just take the day off.
  • Control. It's up to you to make your own business decisions. Want to spend money on advertising? Prefer to charge more or less for your products? Go for it. No need to run a concept up the flagpole, socialize your idea, or gain acceptance for your initiative in the workplace. It's all you, dude.
  • You'll see your accomplishments in black and white (or black and red). As an entrepreneur, any deal you close is the result of your own efforts. How you're doing in operating your business is as clear as looking at your gross and and net revenues.


THE NEGATIVES (Okay, let's be politically correct and call them "Challenges"):

  • There are very few boundaries. What I mean is that as an entrepreneur, you need to be available to provide services to your clients when they are available. If you are running a B2B business, this may be a bit easier since your clients might generally operate Monday through Friday, from 9am to 5pm. But if you service businesses who operate 24/7, or if your target clientele is individual consumers, you need to be available when they are. This may mean evenings or weekends.
  • Uneven workflow. See the boundaries bullet above, this is its kissing cousin. Clients are usually either lining up to hand you their money, or it's like a ghost town and the phone isn't ringing. When the rushes occur, it's all about making time to take on those clients who may walk away (with their money) if you don't provide them service. Working evenings and weekends is pretty common when there's a need to stay on top of work, much less try to get ahead.
  • You don't just have one boss. It's true that you don't have a manager anymore. But every client you take on expects to be listened to and satisfied. And not everybody will be happy with your work the first time (or any time) around, so you will need to work that much harder to meet or exceed their expectations. Keep in mind, clients who love you will provide you with repeat business and referrals; clients who hate you will (at best) fume in silence or (at worst) tell the world they wish you a hot death.
  • Good luck with budgeting. Even the best business rolling on all cylinders has both good months and lean months. Sometimes the issue is not enough new business coming in. Other times it's trouble collecting from your existing clientele. I personally have found it challenging to allocate consistently for retirement and savings due to the inherent variability - even with the most conservative personal budget.
  • It's all on you. Unless you can afford to pay staff or service providers to help you with your work, you will need to find a way to get all the work done. Administrative, strategic, marketing, you name it.



  • Resources to live on while you start and grow the business. You're not going to stop eating or paying rent when you start a new business, and that means the meter is running from the moment you wake up. You'll need a substantial nest egg, a financially supportive partner, or lotto winnings to keep paying for the basics in life.
  • Customer Service. The customer may not always be right, but they're damn close. They always have a right to be heard, and you need to listen because quite often they are giving you information about what they really want, and whether their needs are being met. Providing a customer-centric experience can be a game changer.
  • Marketing. It's fair to say that you can easily spend as much time getting the word out about your business to generate customers as you do on the service you providing service. In the beginning, it's completely about marketing. And implementing a marketing plan can grow rather complicated. Where do you advertise? Who is your target demographic? What should you spend? Do you have a website? How's your SEO?
  • Networking. I have a confession - I don't love the networking aspect of running a business, but I've learned to embrace it because it's essential to growing your brand. You need to always be networking. Keep those relationships alive with past coworkers, chambers of commerce, nonprofit organizations, fellow PTA parents – you name it. It will surprise you when a few folks you network with end up becoming some of your biggest apostles, sharing your business message on your behalf (REWARD THESE PEOPLE!).
  • Multitasking & Organization. Business comes in when it comes in. You can't plan it. You need to be able to juggle various deadlines and provide service promptly. But you also need to be able to switch between your core work that customers are paying you to do and taking (or making) marketing calls. Have organization systems in place to keep track of the progress of all your open items.
  • Endurance. Long hours. Crazy, inconsistent schedules. You need stamina to keep rolling.
  • A thick skin. I've had clients end our business relationship. I've had individuals who have criticized my fees, my marketing, and other aspects of my business. It's critical to learn to take the feedback, gather the important nuggets of wisdom from these, and move forward. No time for sulking (okay, maybe a few minutes of sulking).
  • Adaptability. Find that the way you've been advertising isn't attracting clients like you thought it would? Don't be afraid to try something new. Also, always be learning more about your craft - try to identify a mentor who's been through what you're experiencing, so they can help you identify solutions. Join associations that provide continuing education. Whether it's your core business or your marketing, things are rapidly changing and you'll need to adjust if you wish to stay profitable. You'll need to consistently look at your business and tweak accordingly.
  • Financial Acumen. You don't need to be an accountant, but it's a good idea to understand the basics of bookkeeping and reporting so that you have an up-to-the-minute sense of how your investment of time and money is paying off. Try to look at the return on investment of any activities you conduct; if that sponsorship you made last year didn't translate into any clients, then your money may be better spent elsewhere.

Bottom line: Leaving the structured world of the corporate workplace isn't all ducks and bunnies and rainbows, but it can be absolutely rewarding. Make sure that if you're getting ready to resign and run that yak farm in Montana, that you know what you're getting into.

Scott Singer is the President and Founder of Insider Career Strategies Resume Writing & Career Coaching, a firm dedicated to guiding job seekers and companies through the job search and hiring process. He is a Human Resources professional and staffing expert with almost two decades of in-house corporate HR and staffing firm experience, and is a Certified Professional Resume Writer (CPRW) and Certified Professional Career Coach (CPCC).

Insider Career Strategies provides resume writing, LinkedIn profile development, and career coaching services, including a free resume review. You can email Scott Singer at, or via the website,