7 Questions to Ask Yourself
Before You Go Freelance

How do you launch a successful freelance business? Where do you start? And, considering the state of the economy, should you approach your business launch differently?

These are just some of the questions I’m hearing as more and more professionals leave the corporate world and turn to freelancing as a full-time business or as a supplemental source of income.

There’s no such thing as a one-size-fits-all business plan. And, you can’t cover every aspect of launching a freelance career in a short article. But, in the next few paragraphs, I’ll at least give you a framework to help organize your thoughts and ideas.

#1: Where are you now?

Are you currently employed? Have you recently been laid off? Are you a stay-at-home mom looking to generate some extra part-time income?

Naturally, each of these situations calls for different strategies.

For instance, if you’re a full-time employee and want to eventually quit your day job to become a full-time freelancer, I recommend most people take the “chicken entrepreneur” approach.

A concept popularized by Michael Masterson, being a “chicken entrepreneur” is all about keeping your job (and a steady paycheck) while you initially launch your business to (a) ensure that it’s something you actually enjoy and (b) ensure that it can support your financial needs and goals.

Of course, if you (or your significant other) have recently lost your job and need to start generating income quickly, the situation gets a bit more complex. Yes, you can still become a very successful freelancer, but you need to put things into hyperdrive.

Which brings us to the next question …

#2: How quickly do you need to get there?

Do you need to start generating income over the next 30 days? Or, is your plan to go solo within the next 3 years?

Again, if you’re in a pinch, there are ways to find opportunities fast (more on that in a minute). But, if you have more time (specifically 1 to 3 years), I would put in place a “chicken” transition plan that involves working your business part-time while you keep your day job. Although not everyone has the luxury of time, this is by far the safest method — and everything else being equal, the one with the highest probability of success.

#3: Where can you find (or free up) time to work your business?

You can’t possibly promote your services AND do billable work if you don’t carve out a certain amount of time for your business every week.

So … can you wake up an hour earlier every day? Can you put in an hour or two after the kids are in bed? What about Saturday mornings? Can you work from, say, 5:00 a.m. to noon? Can you work out an arrangement with your employer where you get to telecommute two days a week (and therefore save some commuting time)?

It’s got to come from somewhere, folks. You just have to find it. If you hold a full-time job and commute to work every day, I recognize this will be very difficult to do. But, until the government magically adds four hours to every day through some sort of “bailout bill,” you’ll have to MAKE the time (and be disciplined during that time) if you want to succeed.

#4: What makes you different?

What unique value do you bring to the table — either because of your background, experience, specialized knowledge, skills, aptitudes, connections, or relationships?

Don’t just promote yourself as another freelance copywriter. Tell the world why you’re different and why that matters. Clients aren’t just looking for another copywriter. They’re looking for someone who understands their world, their challenges … and how to solve them creatively.

Help them to make the connection between their challenges and your uniqueness and you’ll have more opportunities than you can handle.

#5: Who do you know?

Some of the most successful freelancers I know launched their careers by leveraging their personal and professional networks. They either approached their previous employer about continuing to do work for them as a freelancer. Or, they landed a great gig or two via friends, colleagues, or family members.

That’s why I always encourage budding solo professionals to spread the word of their plans as often as they can. The world needs to know what you’re up to. But, don’t stop there. Ask everyone you know if they or someone in THEIR network could use someone with your skills and experience on a freelance basis.

Join LinkedIn and other targeted social media sites. Create and frequently update your profile. Let your network know of your plans. Become active in highly-targeted LinkedIn groups and Q&A discussion areas where potential prospects hang out. Answer questions and post comments to demonstrate your expertise (your answers are seen by everyone who clicks on the question, not just the person who asked). And, be generous and sincere with your answers.

One caution about this self-promotion would be if you are using the “chicken entrepreneur” method … you wouldn’t want your current employer to feel you aren’t 100% dedicated to your job. Think about the type of boss you have, and be prepared to answer questions about your side interests if you think it will become a sticky issue.

#6: Where else can you find some quick wins?

Your chances of success as a freelancer go up dramatically when you get quick wins. So when you’re starting out, one of your top goals should be to land paid work (even a small project) as quickly as possible.

Quick wins make the freelance opportunity real. They change it from the success stories you continually hear about others to success you can experience for yourself. They also create momentum. And, momentum breeds more success.

How do you create quick wins? Besides tapping into your network and becoming active in social media sites, you might also consider cold-calling ad agencies. These firms are often looking for skilled copywriters who are dependable and can take on last-minute projects. You can also begin a direct mail campaign, which is a great way to generate potential projects while you work your day job.

I’m not suggesting you do all of these things at once. Start with the avenues that have the highest probability (the people you know). Then, add other elements if you don’t get results quickly.

#7: How will you know when you’re ready?

Finally, if your plan is to moonlight as a freelancer until you have enough business to take the plunge, make sure you define up front (and objectively) what “being ready” means.

What will “being ready” look like in terms of monthly income you need to be generating? Number of steady clients? And, how much of a savings cushion will you need before leaving your job?

Sounds like common sense. But, if you’re not clear about this from the very start, you may miss the signs. Even when it’s obvious to others that you’re ready to make your move.

It’s common to get cold feet when making a big career decision. I remember having serious doubts when it came time to quit my job. I had met all of my financial and business objectives. But I began second-guessing if I was TRULY ready.

Well … here’s the bottom line: You’ll never be 100% ready to launch a freelance career. The key is to know ahead of time what “being ready” means. That way, when the moment comes, you can take the emotion out of it and make a decision based on facts.

If you’re seriously thinking of launching a solo career, make sure to take time and think through these questions early in your planning process. You’ll not only save yourself time and headaches, you’ll also dramatically increase your chances of success.

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Published: April 19, 2010

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