Should you start a freelance business if your job search isn’t panning out?

Trick question. The answer isn’t yes or no, but: “It all depends.” Let’s say your search for a job is failing because your industry now relies on contractors instead of employees. In that case, freelancing may be your best bet for staying in the field.

But if your search is failing because you’re not putting enough energy into it, or because you’re not adapting to the market? Well then, no, don’t go freelance. Dragging your feet and standing in a rut aren’t exactly the formula for business success.

Overall, I’m a big fan of self-employment and freelancing. In my ideal world, everyone would have a side business, if not a big-deal business that pays the bills. Even with all this enthusiasm, however, I find myself assessing job seekers with a jaundiced eye when they announce they’re going freelance. In my observation, these job-search-to-freelancers often fall into one of three categories.

First, there are the lottery players who actually say things like, “If this freelance business works, I won’t have to job search” – a sentiment that clearly shows their entire business plan is based on escaping something rather than building something. They’d be as happy winning the lottery to get out of job search as they would be opening a business. For that matter, who wouldn’t?

Then there are those who will be surprised if they succeed. Their mantra is “I’ll just try this to see if it works.” In other words, they’re going at the problem half-heartedly, which nearly always results in half a business, at most. For freelancers, this means a diet of skimpy contracts with big gaps in-between; they never have quite enough going to actually make a living.

The final group of job-seekers-turned-freelancers are the “hiders” – those who keep claiming to be starting a business but never actually do. Meanwhile, they can’t really look for work either, because it would interfere with this business they’re starting. After a while, job leads stop coming in because everyone’s gotten the message: This job seeker isn’t looking right now.

You can tell from my tone that I get a little impatient with freelancers who aren’t serious about the operation. Here’s why: If you’re not sincere about starting your business, but you let it interfere with your job search, months will pass without success in either arena. In most markets, but especially so in a competitive economy, half-hearted efforts are not rewarded.

I do think that many of the mistakes in the process stem from a basic error in strategy: Most job seekers try to run both efforts on simultaneous but parallel tracks. That is, they tell people that they are both freelancing and job searching. For those in your network, this is like encountering a house with two signs out front: For Sale and For Rent. What a marketing disaster. The homeowner is telling buyers that the house isn’t expected to sell very quickly, while also conveying to renters that living here will be a hassle with little security. Now neither group is interested in the property and it is doomed to sit empty.

Likewise, freelancer-job seekers are telling employers they will be distracted by their own business and they might leave suddenly, while telegraphing to clients that they might close up shop on short notice. Nope, not an attractive sales pitch for either market.

Luckily, in the world of employment, the solution is easy: Instead of selling to two mutually exclusive markets simultaneously, concentrate your efforts in each market successively. That is, instead of seeking both jobs and freelance assignments simultaneously for say, six months, start by intensively seeking freelance work for three months, then switch to job search for the following three months, if needed.

Assuming that you’re selling the same skill set in both cases – say, grant writing or technical consulting – this stacked approach will have several advantages. By starting with the freelance process, you scratch an itch, but you also create the most logical stepping stone between the two options. That’s because your efforts to find freelance work can inform your job search in the second stage and also because some of the freelance seeds you sow in the first three months could still blossom in the job search stage of your outreach. If that happens, you will have the option of continuing your search and doing the freelance work on the side or of switching more fully to freelance.

In either case, your next step is clear: You need to build the freelance business into something that could potentially support you. I’ll tackle that question in next week’s column.

Amy Lindgren owns Prototype Career Service, a career consulting firm in St. Paul. She can be reached at alindgren@prototypecareerservice.com or at 626 Armstrong Avenue, St. Paul, MN 55102.