7 Questions to Ask Yourself Before Going Freelance
Who hasn’t thought about quitting their full-time job and going out on their own? Being your own boss is certainly tempting. But is giving up your status as a regular employee the right choice for you?
What the Experts Say
“There are many reasons why people choose to go freelance,” says Steve King, partner at Emergent Research. “We’ve studied this for many years, and it really boils down to autonomy, control, and flexibility: the autonomy to work in the way they want to, control over what they do, and the flexibility to work when and where they want.” No matter the reason behind the decision, people generally don’t look back,” says Sara Horowitz, the head of the Freelancers Union and author of The Freelancer’s Bible. In fact, a study by the Freelancers Union found that 88% of people say they wouldn’t return to a full-time job. Horowitz says that most are happy to be done with “the brutal schedule, the way work is organized, and office politics.” Still, freelancing isn’t without its challenges. What people envision and reality are often very different. Here are the questions to ask yourself before making the leap.
Do you have a marketable skill?
“The first step is to make sure that you have a skill that’s in demand,” says King. These are typically specific, functional abilities like project management, web development, financial analysis — or advisory skills that come from years of experience. “If you’re 22 and you’re not a web developer, you probably don’t have marketable skills,” he warns. The media and technology sectors have traditionally been the biggest employers of freelancers but the good news is that “almost every industry is expanding their use of contingent workers,” says King. If you’re not sure whether you have skills that potential clients would pay for, consider testing the market by doing some moonlighting while you are still gainfully employed. (More on that below.)
Do you have a robust network?
“Freelancers who are connected to others tend to do best economically,” says Horowitz, because those connections become a significant source of business. But don’t despair if you don’t yet have an extensive professional network. You can build one even before you leave your job by attending relevant conferences, reaching out to people through LinkedIn or Twitter, or joining a group of freelancers or small business owners in your area. Go beyond work contacts too; “think about your friends, neighbors, and other people you know,” says King. Let them know when you go out on your own and encourage them to spread the word. Remember also that your network isn’t just about drumming up business. “The most successful freelancers know how to use their network for all sorts of things, like outsourcing work when they have too much,” Horowitz explains. A critical component of your network is a friend or former colleague who is already freelancing and can point you to resources. As with any career transition, it’s important to seek advice from those with more experience and expertise than you.
Do you have the right temperament?
Do you have a financial cushion?
“If you can’t go without income for three to six months, don’t even think about it,” says King. Horowitz agrees that you need a financial buffer to weather any lulls in work. “Really tear your expenses down. Assess where you live. Don’t set yourself up by having a ton of overhead,” she advises. “You should build your expenses in a way that if you hit a dry patch, you’ll be ok — and the more cushion, the better,” says King. This is especially important for people who don’t have the financial support of a spouse with a more stable job and benefits. Freelancing can come with a lot of uncertainty — you may not always know who your next client is going to be or how much you’re going to earn in the coming year. “You have to be able to deal with ambiguity,” says King. Horowitz says that you need to be able to put away 40% of every paycheck to cover your taxes, health and life insurance, vacations and retirement. Underestimating costs that employers typically take out of your paycheck or cover is “the biggest thing that bites people,” she says. Consider which perks you want to keep and how you’ll pay for them.
Are you disciplined about work?
Some people do best when they have a manager to answer to or structure to their days. If that’s you, freelancing is probably a bad idea. “You need to be self-motivated, have good organizational skills, and a strong work ethic,” explains King. And you must be comfortable doing all sorts of things that aren’t directly related to your work. When you’re on your own, you’re your own boss, IT person, HR representative, benefits administrator, head of sales, and administrative assistant. You also have to be familiar with the laws around taxes and legal liability. You need to be OK filling all of these roles, even the ones that aren’t glamorous or your cup of tea. Sure, you may eventually be able to outsource some undesirable tasks but at least at the beginning, they will fall to you. You have to think of yourself not just as a contractor, but as the head of a small business.
Can you try it out?
If you’ve answered yes to all the questions above, Horowitz suggests experimenting with freelancing before you quit your day job. “It doesn’t have to be an on/off switch” — one day you’re a full-time employee and the next you’re on your own, she says. You can ease your way into the freelance life. In fact, “most people explore on the side” to get a taste of what the work will be like and test out their business plan, King says. If you decide to go for it, you’ll already have your business set up and some clients in the queue. But do make sure you’re not violating any of your current company’s policies or your employment contract.
Can your current employer be your first client?
“A good chunk of independent consultants — 20 to 25% — report that their first customer is their current employer,” says King. So consider whether there’s part of your current job that you could do as a freelancer and feel out those possibilities before you give notice. “If you have good rapport with your boss, tell him that you’re considering going out on your own, then ask, “If I did that, is there some way that I could continue my relationship with the company?’” King suggests. Some employers, especially large corporations, won’t let you work as an independent contractor immediately after leaving your job because of their interpretation of IRS rules. “Many have a waiting period of six months to a year,” King says. But you can still keep the relationship on the back burner while you line up more immediate revenue sources. And even if your former employer doesn’t ever become a client, it’s important to maintain a positive connection with your old colleagues. “They are a really important component of your network,” says King, and you never know who might want to employ you down the line.
Principles to Remember
Make sure you have a strong network of people who can help you find work
Give yourself a financial cushion before going out on your own — you need to be able to weather any dry spells
Be prepared to take on tasks that aren’t directly related to your work, such as handling IT issues, sending invoices, and selling your services
Assume that your skills and experience are something that clients are willing to pay for — consider testing the market before officially going freelance
Go freelance if you’re not self-directed or comfortable with ambiguity
Leave your job until you have a plan in place, even if it’s not 100% certain
Case Study #1: A vague plan is better than no plan
Four years ago, Allie Rogovin was managing a new team designed to promote diversity at Teach for America. She’d been at the organization for 13 years, loved its people and mission and was enjoying the latest challenge, but she wanted to scale back. “I had two kids at home and the 80-hour work week was hard,” she explains. “I had all the flexibility that I could ask for. I came in when I wanted to, I could go on a field trip with my daughter. But it was just a crushing workload. I didn’t feel like I was doing my TFA job well, and I didn’t feel like I was doing my mothering job well either.”
After talking with her husband, she decided to quit in July 2011. She knew that she eventually wanted to consult and had already identified a need in the marketplace she could fill. “In my position at TFA, I had spent a lot of time talking to small education nonprofits who needed help getting a talent function off the ground. I was really motivated by the idea of helping these younger, less established organizations do what I had done at TFA,” she explains.
But she didn’t have any clients lined up when she left TFA. “It’s probably not the most thoughtful thing I’ve ever done, but I needed the break,” she explains. “We were lucky that my husband had a good job and we’d been smart about our finances. We sat down and looked at the amount of money we’d need coming in and made small changes to how we lived to help us through my time off.”
After four months focusing on her family, she reached out to her network to announce that she was starting her own business. A friend responded with “I have a client who you would be great for” and, by January, she had her first consulting gig. Soon after, she added TFA to her client list, signing on to coach some of its senior managers.
In the time since, Allie says she’s come a long way: “When I first started out I had some doubts that people would find my skillset useful. I thought, ‘Would anyone really want to hire me?’ Now I have a one-pager and a standard pitch and a business email address. Most importantly, I know exactly what kind of projects I enjoy doing most.”
Case study #2: Your network is bigger than you think
The autonomy of being her own boss had always appealed to Sunita Malhotra. “I had been talking about working for myself for ten of the 20 years I was in corporate life,” she says. But there were several obstacles: she enjoyed the job she had (HR director at a global organization in Europe), she wasn’t entirely confident that she had enough experience to consult, and most importantly, she didn’t want to give up her medical insurance and pension. “That’s what stopped me for many, many years,” she explains. But over the 2006 Christmas holiday, she finally decided to take the leap. She’d been talking again about going out on her own and her husband told her “just do it.” He also offered to cover her through his employee benefits.
Sunita didn’t quit her job to freelance right away, but she set the process in motion. “From January to April, I focused on getting my act together,” she says. “It’s very helpful to have a supportive spouse. We sat down and did financial planning. We asked, what is the bare minimum we need to live? And what are the sacrifices we could make?”
At the same time, she also developed a seven-year business plan. “I thought hard about what my core business would be. What things was I best at that I could do for the rest of my life with a smile on my face?” She also identified roles she didn’t want to play. “I knew I could do training, for example, but there are tons of companies doing that, and I didn’t want to compete in an overcrowded market. I wanted to create my own niche.”
She stopped short of going after clients, however. “I didn’t feel ethically comfortable doing that while I was still employed,” she explains. Besides, “I was exhausted” working full-time and planning a new career in evenings and on weekends. “I’m not even sure where I would’ve found the time to moonlight.”
Once she felt she had a solid plan, she gave her notice to her employer and began sending out feelers to former colleagues. “I had no clue who my first client was going to be. That was the scary part,” she says. But her network came through. Her first client was a supplier to whom she had given a break years before. Her second client came through a person she had also worked with earlier in her career. “It was a bit of luck but I had a much bigger network than I realized,” she says.
Of course, she discovered some downsides to being a freelancer: “You get spoiled in corporate life. I had an assistant, IT support. Now, I’m CEO but I’m also the IT person, the finance manager, and the office manager.” But eight years in, Sunita says she would never go back.
“人们选择做自由职业，有许多原因。”Emergent Research 合伙人Steve King说。“我们研究这个现象有好多年，而这一切归结为自由、控制权、以及灵活性：以自己所要的方式工作的自由，控制自己所做的事，以及在任何时间、任何地点工作的灵活性。”不管这个决定背后的原因是什么，人们通常不会回头。”自由职业者联盟主席兼《自由职业者圣经》（The Freelancer’s Bible）作者Sara Horowitz说道。事实上，自由职业者联盟进行的一项研究显示，有88%的人说他们不会回到全职工作。Horowitz说，大多数的人很高兴不再需要面对“残酷的时间表、工作组织的方式、以及办公室政治。”尽管如此，自由职业不无它的挑战。人们的想象和现实，往往很不一样。在跨出这一步之前，要先问自己这几个问题。
四年前，Allie Rogovin在管理一个新的团队来促进“为美国而教”（Teach for America，简称TFA）里的多样化。她在组织工作了13年，爱着那里的人和宗旨，并且享受着最新的挑战，但是她想缩减她的工作。“我在家里有两个小孩，而一周工作80个小时，非常困难。”她解释。“我在工作的灵活性，达到了我的期望。我可以选择自己的工作时间，我可以和我的女儿去校外考察旅行。但是我的工作量简直难以负担。我感觉自己不能把TFA的工作做好，也感觉到不能把母亲的工作做好。”