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.

Attending a Writer’s Conference Can Make a Difference in Your Career

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If your goal for 2020 is to get more serious about your writing career, then you might want to consider attending a writer’s conference.

There are plenty of reasons to attend a conference: to find an editor, to connect with an agent, to learn more about your craft, to gain motivation, to expand your network, among others. Only you know what you want to accomplish when you get there.

Knowing which conference to attend can be daunting however. There are numerous conferences to choose from and there seems to be more every year. Which one you choose to attend will depend on your budget, of course, the location, and perhaps the size of the event. It’s also important to consider your goal for the conference: what do you hope to achieve while you are there? You might also be enticed by the editors and agents who plan to attend, or who the keynote speaker will be.

Your best bet is to choose a conference that is a) locally accessible and b) serves your genre. That way you know you can spend time with other like-minded professionals who are writing within the same genre and you can connect with editors and literary agents who specialize in that genre. For example, if you write science fiction or fantasy, your best bet is to attend a writer’s conference for the sci-fi genre, though you can get just as much out of a general writer’s conference too.

If cost is a concern, check conference websites for information about scholarships. Some conferences do offer scholarships for part or all of the cost of the conference, so it might be worthwhile to check it out. Also, some states offer grants for individual artists to pursue a professional development goal or complete a project. For example, the Illinois Arts Council offers grants for individuals artists (although as of this writing, funding has been expended and won’t continue until 2021).

Below is a brief list of writer’s conferences for the first half of this year. There are plenty more in the second half, but most of them have not published dates or registration information just yet. Most of the conferences listed below are located in the Midwest, close to where I live. If you live elsewhere, check Google for writing conferences and university-sponsored workshops close to you. Later this year, I’ll do a follow up post about scheduled conferences for the second half of the year. Stay tuned.

What about you? Have you attended a writer’s conference? Where did you go? What was your experience like?

March

Midwest Writers Workshop Agent Fest
Ball State University, Muncie, Indiana
March 13-14, 2020

Let’s Just Write! An Uncommon Writers Conference
Presented by Chicago Writers Association
Chicago, Illinois
March 21-22, 2020

University of Wisconsin Writers Institute
Madison, Wisconsin
March 26-29, 2020

Southern Kentucky Writers Conference and Bookfest
Bowling Green, Kentucky
March 30, 2020

April

Screencraft Writers Summit
Chicago, Illinois
April 24-27, 2020

Spring Fling Writers Conference
Presented by Chicago-North Romance Writers of America
Chicago, Illinois
April 30-May 3, 2020

May

Blue Ridge Mountains Christian Writers Conference
Black Mountain, North Carolina
May 24-28, 2020

Bear River Writers Conference
University of Michigan
May 28-June 1, 2020

Indiana University Writers Conference
Bloomington, Indiana
May 30-June 3, 2020

June

Rutgers-New Brunswick Writers Conference
Rutgers University, New Brunswick, New Jersey
June 5-7, 2020

Write by the Lake Workshop and Retreat  (not a conference, but a working retreat)
University of Wisconsin-Madison
June 15-19, 2020

Write-to-Publish Conference
Wheaton College, Wheaton, Illinois
June 17-20, 2020

Minnesota Northwoods Writers Conference
Bemidji State University, Bemidji, Minnesota
June 22-28, 2020

Jackson Hole Writers Conference
Jackson, Wyoming
June 25-27, 2020

And the big daddy of them all:

Writers Digest Annual Conference
New York City
August 13-16, 2020

More conference listings to come later this spring.

How Creative People Can Survive in Non-Creative Jobs

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When you think of a creative person, what images comes to mind? An improvisational comedian? A ballet dancer, an artist or songwriter?  Do you ever stop to consider that maybe business owners and company CEOs have a creative spirit too? It’s not always obvious to the rest of us. But I believe they could not have reached their level of success without having some creative juice coursing through their veins. The rest of us don’t always get to see it.

I believe we are all born with creative gifts. It doesn’t matter if you are the company CEO, the sales manager or the guy in the mailroom. We all have a creative source within us that begs to be exercised. It is no wonder I see so many people leave the rat race to write a novel, pursue a singing career or become a curator at an art museum.

Working in a dull 9-to-5 job can sometimes stifle that creativity – but it doesn’t have to. I worked for 10 years as an administrative assistant, which required little, if any creativity. Between making travel arrangements for VIPs, organizing files, updating monthly spreadsheets and making sure the supply room was well stocked, there wasn’t a lot of room for more imaginative endeavors. But I was also blessed to work with managers who understood my need to indulge my creative talents, even if it was only to design a flyer or write a customer service letter.

If you believe the corporate world has robbed you of your creative edge, don’t lose hope. Your creative spirit is alive and well. It just needs an environment in which to thrive.

But don’t sit around waiting for inspiration to strike. Be proactive. Look around the office for opportunities to express your creativity. Here are a few ideas:

* Be a problem solver. Solving problems is a valuable skill in the workplace, often requiring thinking outside the box. To solve problems, you have to tap into that creative reservoir within yourself. Whether it’s coming up with a complex solution to a long-standing customer relations issue or developing a new product that can change the way people work, creativity is at the heart of these innovations. And innovation is what drives businesses to grow and prosper.

* Learn new software programs. Teach yourself to do desktop publishing using Adobe InDesign or create Power Point presentations. As you gain more experience doing design work, you can add samples to your portfolio and become a valuable go-to design resource for your friends and colleagues, who may not have the design skills you just acquired.

* Plan events and parties. In a small office especially, you may have to wear many hats. Event planning may be one of them. Maybe you are assigned the task of planning a co-worker’s work anniversary celebration, a meeting of the board of directors, or the annual Christmas party for the office staff. Surprise parties are even better, because they challenge you to come up with creative ways to keep the party a secret. And decorating the office party room naturally lends itself to creative expression.

If meeting planning is not in your job description and it’s something you want to break into, ask your boss or the person in charge of planning meetings if you can help. You not only show your creative side and your initiative.

* Display your artwork. Are you an artist, painter or photographer? Ask your boss or manager if they are willing to display your artwork in your office. At a nearby yoga studio I regularly attend, one of the instructors recently displayed her artwork around the studio. It was a great opportunity to showcase her talents and sell her work to studio clients.

* Display your writing skills. Writing skills are highly valued and often overlooked in the workplace. If you like to write and have a talent for telling amusing stories, there may be opportunities for writing that can be an outlet for your creative genius. Offer to write customer service letters for your boss or the sales department. Ask the marketing director if you can contribute to the company blog or write articles for their newsletter.

I once worked as a temp at a Japanese-owned property management company that managed multiple hotels around the world. One day, the president of the company, who spoke very little English, asked me to write a thank-you letter to a friend who had taken he and his wife out to dinner. I quickly drafted a letter – only three sentences – and showed it to the president. From his wide smile and enthusiastic nod of his head, I knew I had hit the mark. No matter what type of company you work at, good writing skills will always be valued by higher-ups.

* Get a side gig. It seems many workers are doing side gigs these days. For many, it helps them bring in more money. For others, the side gig does what the day job cannot do – feed the creative soul.

These are just a few ideas to get you thinking about other ways to add a creative edge to your non-creative job. Brainstorm with co-workers and your boss, and see what you come up with. That alone is a creative challenge.

You can’t always change the circumstances of your job (unless you change jobs), but you can change the way you think about your job. Sometimes, by simply accepting the fact that you work in an unimaginative office environment allows you to see opportunities for contributing your creative skills that you may not have noticed before. And that can make the day job all the more tolerable.

When a Former Employer Comes Calling, Should You Answer?

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Have you ever worked for a former boss or employer? And if you did, was your partnership as successful the second time around? Or did you hit a dead end?

Twice in my career I’ve been approached by former employers to work for them. In one case, a former supervisor invited me to be her administrative assistant 18 months after joining a new company. All signs pointed to yes. I loved working for her the first time around, I was stuck in a dead end job, and the new job paid about $5,000 more than what I was making. So I said yes, though I left 18 months later to pursue another opportunity.

More recently, I was invited by a former employer to manage their bi-monthly magazine. While I was flattered that they thought of me for this role, I didn’t feel I was the right fit for the job. With a new CEO on board, the company was going through a transition and the culture of the organization had changed. I didn’t want to lock myself into a stressful, political situation, and I wanted to be free to pursue my own creative writing. So I told them no.

Looking back, I do not regret either decision. Both situations have worked out fine. In the first scenario, in the short time I was there, I gained valuable experience in a new work environment. In the second scenario, I realized I did not have a lot to gain personally or professionally from rejoining a former employer. The organization  eventually hired a new manager who brings a sorely-needed fresh perspective to their publication.

If a former boss comes calling, would you jump at the opportunity? Whether you accept or decline the offer depends on what your needs are. There are reasons to accept, and reasons to say “No, thank you.”

Reasons to accept an opportunity with a former employer: 

It helps build your resume. Additional or different responsibilities stretches your professional muscles. Perhaps you have an opportunity to manage a department, oversee a project, or supervise staff that you did not have previously. Even if you hold on to this situation for one year, that experience looks good on your resume.

It offers a higher salary. Financial stability is always a plus, but don’t accept a job only because of the salary. You need to weigh other factors too, such as compatibility with co-workers and the supervisor, and opportunities for career growth. Taking a job, or staying in one, just for the money and benefits can hurt your morale. In my experience, these types of work situations tend not to work out well for the long term. And you may find yourself hitting the pavement again in six months after realizing that the job wasn’t’ everything it was cracked up to be.

You like the person you’d be working for. All things considered, when you like your boss and you have a strong bond with them, it makes it possible to like the job, even if it isn’t exactly the type of job you wanted. Having a good relationship with your boss can help get you through difficult work projects. Just be aware that your relationship with a former boss in a different corporate culture can put pressure on your relationship, and working for this person my not be so enjoyable the second time around.

Reasons to decline an opportunity with a previous employer: 

The company does not have a good reputation. Do your homework about the company. Just because a former boss invites you to work for them doesn’t mean the new company is right for you. The culture of the organization may not be compatible with your personality. Use social media to find current and former employees. Did the company treat its employees well? Is the company experiencing layoffs or going through a difficult managerial transition? While some change in the corporate culture is necessary to weed out outdated systems and processes, you don’t want to work in hostile, unstable work environment.

The opportunity does not fit in with your long-term career goals. Or you want to do something completely different. Our career goals are constantly changing. What might have been an exciting opportunity five years ago may no longer thrill you because you’ve moved on to different career options. If you’ve had writing jobs most of your adult life and you find you’d rather teach children, then no lucrative job offer is going to make you happy.

The job is too much like what you’ve done before. The office space and co-workers may change, but the work does not. The new opportunity might pay well and offer great benefits and growth opportunities, but if you find yourself doing the same type of work that you did before, and there’s not room for career growth, it’s probably time for a career reassessment. There’s nothing more disheartening than being stuck in a job with little opportunity for advancement and smacks of the same-old, same old.

It can be flattering when a former boss comes calling, but keep in mind that any new opportunity that arises should be a win-win situation. You should benefit from this opportunity as much as your boss does.

Listen patiently to their proposal and ask a lot of questions. Don’t fall for any carrot-on-the-end-of-the-stick proposals that your former boss might present to you. Those proposals may never materialize or they may benefit your boss more than you.

Know yourself and always keep a clear vision of your career goals. As long as you keep those goals in sight, you will never be steered in the wrong career direction. If you feel the opportunity does not meet your professional goals, then it’s okay to say, “Thanks, but no thanks.”