7 Questions to Ask Yourself Before You Quit Your Day Job

How do you launch a successful freelance business? Where do you even start?

There’s no such thing as a one-size-fits-all business plan. And I 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 for organizing 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?

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 usually recommend the “chicken entrepreneur” approach.

A concept popularized by bestselling business author, Michael Masterson, being a “chicken entrepreneur” is all about keeping your job (and a steady paycheck) while you launch your business. This allows you to confirm that running your own business is something you actually enjoy, and that it can support your financial needs and goals.

Of course, if you’ve lost your job and need to start generating income quickly, the situation is more complex. Yes, you can still become a very successful freelancer, but you need to put things into hyper drive.

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

Which brings us to the next question. How quickly do you need to ramp up? Do you need to start generating income over the next 30 days? Or, do you plan to go solo sometime in the next three years?

If you’re in a pinch, there are ways to find opportunities fast. But if you have some time (specifically one to three years), I would put in place a “chicken” transition plan that involves working your business part-time while you keep your day job.

That’s precisely what Kathryn Messer and many other coaching clients of mine have done.

Not everyone has the luxury of time, but this is by far the safest (and most successful) method—everything else being equal.

#3: Where can you find time to work on your business?

You can’t promote your services AND perform billable work if you don’t carve out some time 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 weekends? Can you work from, say, 5:00 a.m. to noon on Saturday mornings? Can you make an arrangement with your employer where you telecommute two days a week (and therefore save on commuting time)?

The time has got to come from somewhere. You have to find it. And if you can’t find it, you have to make it.

If you hold a full-time job and commute to work every day, I recognize that this will be difficult to do. But you’ll have to MAKE the time some way or another if you want to succeed.

And just as important, you have make sure you use that time as productively as possible.

#4: What makes you different?

What unique value do you bring to the table? What about your background, experience, knowledge, skills, aptitudes, connections or relationships distinguishes you from the pack?

It’s not enough to promote yourself as just another freelance writer. Tell the world why you’re different, and why that difference matters. Clients aren’t looking for just another freelancer. They’re looking for someone who understands their challenges—and knows how to solve them creatively.

If you can help clients make the connection between their challenges and your differentiation, 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. Some approached their previous employer about continuing to do work for them as a freelancer. Others landed good gigs via friends, colleagues or family members.

That’s why I encourage budding solo professionals to spread word of their plans as much as possible. Let the world know what you’re up to. Ask everyone you know if they (or someone in their network ) can use someone with your skills and experience on a freelance basis.

Join LinkedIn and other targeted social media sites. Create and update your profile. Let your network know of your plans.

Become active in LinkedIn groups, online discussion forums and other “places” (online and offline) where your prospects hang out. Answer questions and post comments to demonstrate your expertise. Be generous and sincere with your ideas and advice.

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

Your chance of success as a freelancer goes up dramatically when you get quick wins. That’s why, 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 move it away from “success stories you hear about” to success you experience for yourself. Quick wins also create momentum. And momentum breeds more success.

How do you create quick wins? Besides tapping into your network, you can also approach agencies or other firms that hire freelancers when they can’t fully staff projects with internal resources. These firms are often looking for skilled professionals who are dependable and can take on last-minute projects.

You can also leverage direct mail and email (if used correctly) to generate potential clients while you work your day job.

I’m not suggesting you do all these things at once. Start with the avenues that have the highest probability of success (which is usually tapping your network). 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 what “being ready” means.

What does “being ready” look like in terms of monthly income? Number of clients? How much of a savings cushion will you need before leaving your job?

This may sound like common sense. But if you’re not clear about what “being ready” means from the start, you may miss the signs.

And remember: It’s common to get cold feet when making big career decisions. 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 now doubted whether I was TRULY ready.

Well…here’s the bottom line: You’ll never be 100% ready to launch a freelance career.

It’s supposed to feel scary. That’s normal.

But by setting some parameters at the start, you can remove some of the emotion from the decision when the time comes and base it on facts, not fear.

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