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.

Tips for Managing Your Writing Expectations

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As creative writers, it’s easy to fall prey to unrealistic expectations. Writers must strike a balance between expectations that are too low or goals that are set too high. If expectations are too low, they may be a product of fears and self-doubt that our writing is not good enough. If expectations are too high, they may reveal an overly optimistic view of talents and skills that haven’t been mastered.

Developing a healthy balance between the two can provide a more realistic vision of your writing. The more realistic your expectations are, the more easily you’ll be able to achieve your writing goals. Here’s how you can manage your expectations as a writer.

1. Assess your skill set. Make a list of all your skills. What are you especially good at doing? Are there certain skills that you need to learn? For example, do you need to learn how to edit yourself? Or do you need to develop a better ear for dialogue? When you assess your skill set, you gain a clear understanding of your strengths and limitations.

2. Assess your writing goals. Think about the types of writing you want to do. Do you want to write fiction or screenplays, or are you happy writing for businesses?  Do you want to be a published author, or do you prefer to write as a hobby? Do you want to be paid for your writing? If so, research places like Writer’s Market for information about paid writing markets. What time frame do you want to achieve these goals? Some can be achieved within a year while others may take several years. Still others may never be realized. You may need to prioritize these goals and set milestones for achieving the larger ones.

3. Check in with yourself periodically. Goals and expectations can change over time. Set aside time every quarter (ideally) or at least every six months to review your writing goals to determine if you are still on track. When you reassess your plan every few months, you can make adjustments along the way so you stay on track.

4. Seek a second opinion. If you feel stuck and you’re not sure where to go next with your writing, it might help to get the perspective of a friend or two. It may be that you aimed too high with your writing or your expectations are too low. They can provide valuable insights into your approach. For example, if you lack self-confidence, they might point out some of your strengths that you can capitalize on. Or if you are painting an overly rosy picture of your writing life, like writing an 800-page novel in the next six months, they can provide needed perspective so you can see if that is a realistic goal.

5. Challenge your inner critic. Writers are naturally born with an inner critic, a voice that tells them their writing stinks. When you notice that voice in your head, stop for a moment and challenge those thoughts. Who is really thinking them – you or someone else? Counter with a positive affirmation in return. For example, if the voice keeps telling you that no one will like your story, counter it by pointing out all the times when someone DID like your story. Keep countering that critic with success stories of your own until that voice is silenced for good.

Or put a sign on your wall: “Inner critics not allowed while creative genius is at work.” Or something similar. The sign serves as a constant reminder that what matters most is your opinion, not someone else’s.

6. Expect rejection. No matter what kind of writing you do, rejection is bound to happen. Someone somewhere will be reviewing your work, and not everyone will like what you write. Rejection is a natural part of the writing process. Rejection can help you reassess your writing project to see if it still works. It can help you look at other avenues for publishing that you might not have considered. If two editors didn’t like your piece about making your own food for cats, then maybe a third editor will. Rejection can be disarming at first, but it can also fuel your motivation to keep trying.

7. Let go of the need to be perfect. When you first begin writing, you might envision what your final piece will look like. Then as you begin writing, you realize that your piece is nothing at all like you imagined. Perhaps you write a dozen or so drafts before finally giving up. First drafts are supposed to be crap, says essayist Anne Lamott in her book Bird by Bird. Know this and accept it. First drafts help you unload the ideas from your head to the paper before you can craft them into a story. If you try to be perfect as you write, you will never accomplish much. All you will have to show for your effort is a waste basket filled with crumpled sheets of paper.

Unrealistic expectations are often the result of feelings of inferiority or idealized visions of writing success. Neither of them are satisfactory. Keep your expectations realistic by periodically assessing your skills and emotional mindset.