Is Self-employment Right for You? First, Ask Yourself These Questions

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Remember to check out this week’s writing prompt on my home page.

Many of us have dreams of hanging out our own shingle and taking charge of our livelihoods. For most of us, that’s all it is – a dream.

Many people who have started a business often wind up closing up shop within a year or two. They had difficulty finding clients or lost money before deciding that they weren’t as prepared for the solo gig as they thought. So they went back to working for someone else, preferring the stability of a steady gig and paycheck.

Working for yourself is hard work. Harder than most people expect when they start out.  The fact is, not everyone is cut out to own their own business. It’s more than the financial support and resources that can keep the business going; it’s your own mental and emotional make-up that can put a kink in your plans. Some people simply don’t have the fortitude, organizational skills and network to make the business work. Others don’t like the uncertainty about the future or fear rejection.

I fell into my solo writing career accidentally. I had left a job to manage a small business part time, but I was miserable. I quickly realized that this was not what I wanted to do. My former boss reached out to me to do a writing assignment for him, which led to other assignments. At the time, I wasn’t sure what I wanted to do (although I knew I wanted to get out of the business management gig). Did I want to freelance full time, or were these writing assignments just a temporary fix until I could figure things out? Seven years later, I’m still trying to answer that question.

Looking back at that period of my career, I wish I had taken more time to think things through. I would have liked to have had a handbook or a self-assessment worksheet to help me figure out whether going solo was the right path for me.

The folks at the career site Vault have put together a really nice infographic that outlines a number of questions to ask yourself before deciding if freelancing is right for you.

Below are some questions taken from this infographic as well as a few of my own I wish I had asked myself. Hope these questions help you decide whether you’re ready for a solo career or not.

  1. Why do you want to work for yourself? Knowing why you want to work for yourself can help you feel grounded, especially when things don’t go as smoothly as you hope. Whenever you feel lost on your solo journey, come back to your why. It will help you refocus on your career goal.
  2. Do you have an established network and support system in place? Just because you decide to go solo doesn’t mean you work alone. You still have a support team around you, such as an attorney and/or accountant, a marketing person if you don’t plan to do it yourself, maybe someone to handle social media. Then there is your personal support team – your spouse, friends and family, and former colleagues who can pitch in when you need help.
  3. Do you enjoy working for yourself? Some people love working alone and have no trouble being in quiet surroundings. Others need to bounce ideas off other people. They’re more productive working in a collaborative environment. If you need to be surrounded by people in order to be productive, you may struggle working on your own. Then again, there are always libraries and coffee shops to make you feel you are surrounded by “co-workers.”
  4. How much of a financial foundation do you have? Most financial experts suggest having a nest egg of six months for living expenses while you launch your business. I would suggest more than six months, at least a year. For one thing, things are more expensive than you realize. Second, you’ll need cash on hand in case of emergencies, like a root canal or household emergencies.
  5. Do you have your first client or project to start? It might help your solo venture if you already have a client or two in place. They’ll provide the moral and financial support you need to build on for the future.
  6. How do you respond to uncertainty? Once you’re on your own, you’ll no longer have a steady paycheck, which means the future is very uncertain. That uncertainty can be too scary for some people. If you prefer the steadiness of a routine paycheck, then working solo may not be right for you.
  7. How are your time management skills? When working on your own, you won’t have to follow someone else’s schedule. You’ll be in charge of your own, or that of your client’s. In fact, if you have multiple clients, you’ll have to juggle priorities and that means having solid time management and organizational skills to keep track of them all.
  8. How much of a risk taker are you? This question might be easier to answer on a spectrum of one to 10, one being not much of a risk taker at all and 10 being “bring it on.” Knowing your comfort level with risk can help you determine what you’re willing to put up with as a solo artist – and for how long. Taking the leap into your own business is a huge risk, one that not many people are willing to take.
  9. How long are you prepared to go it alone? Experts say that most businesses don’t last longer than one year. One year is the barometer to decide if a solo venture is going to work out or not. For others, they simply run out of money or they lose heart in the project after six months to a year. If you’re in it for the long haul, then going solo may work out for you.
  10. How much experience do you bring from your chose field? Someone with only five years’ experience may not find as much success on their own as someone who has done the same work for more than fifteen years.
  11. How do you respond to new challenges? Some people welcome new challenges, and in fact, actively seek them out to spice up their lives. These people are more likely to succeed as solo business owners.
  12. How do you deal with rejection? Rejection is part of business. The most successful business owners will likely let the rejection slide off their backs or use it to fuel their next venture. They don’t give up. If you are easily discouraged by rejection, then working for yourself may not be right for you.
  13. How confident do you feel about your skills and prospects for success? The more confident you feel about yourself, the more positive impression you will make on clients and customers.
  14. How resilient are you? This question goes along with the rejection question. Are you able to bounce back after disappointment, such as a lost client or failed sales call? Most successful people working on their own are able to bounce back more easily because they understand that it’s only a temporary setback.
  15. Are you comfortable wearing many hats? Working on your own means doing a variety of tasks, everything from accounting, marketing, recruiting, even housekeeping. All of this in addition to your own unique skill, whether that’s copywriting, graphic design or pet care. You might be good at what you do and the reason you want to work for yourself, but you may not feel comfortable or have the skills to do the other tasks. You’ll have to figure out what you are willing to do and what you should outsource.

As you can see, working for yourself requires more than just basic business skills. It requires emotional and psychological strength to withstand the challenges of business ownership. By answering these questions honestly, you can decide if working for yourself is the right career path for you.