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The Freelancer’s Guide to Bootstrapping

You’ve attended holiday family gatherings, right? For me, there are always a few things guaranteed to happen:

  1. My kids eat only bread, while other people’s children happily eat Aunt Patchouli’s kale salad.
  2. I eat precisely three too many bites of pie, and seriously consider drinking from the gravy boat.
  3. One of the uncles or grandpas complains about the “kids today” (probably the ones eating only bread) and talks about “pulling himself up from his bootstraps.”

Bootstraps. I don’t think I’ve ever paid enough attention to boots to know if they’ve got straps, but I’ve definitely heard about them. So, what, exactly, does “bootstrapping” mean? Where did the phrase come from? Let’s unpack it for a minute, here.

According to good ole Merriam-Webster, a bootstrap is “a looped strap sewed at the side or the rear top of a boot to help in pulling it on.” It goes further to the plural form, which then turns it into the metaphor we’re more familiar with: “unaided efforts.”

So, what crotchety Uncle Jasper is trying to tell you (while interrupting your pie enjoyment) is that he’s gotten where he is today without the help of anyone else. Whether this is actually true or not is a mystery, but there’s still something us freelancers can learn from Uncle J.

When you apply the term “bootstrapping” to entrepreneurship, you’ll most likely find yourself wading through a lot of information about “startups.” Should we unpack that term, too? Merriam-Webster defines “startup” as a “fledgeling business enterprise.”

I would like to enhance that definition by adding “founded by people who make the most out of what they’ve got.”

Starting a business is expensive, and the startup culture that has cropped up within the last ten or so years has become notorious for its resourcefulness and creative frugality.

But… you’re just flying solo, right? What does this have to do with freelancing?

Here’s the deal: freelancers can learn a gravy-boatload from startups and their bootstrapping expertise.

Bootstrapping focuses on using creativity rather than funds in order to expand business.

Think of it as punching your freelancing game up to a whole new level.

Snuggle Up to Your Niche

Here’s your dilemma: you’ve got the talent, the time, and the need to work. You just need to get the word out. You can’t afford to pay a professional marketer, and you can’t afford to buy newspaper ads, pay for a billboard, and film a TV commercial that’s shown during prime time. So what do you do?

First, of course, you’ll need to reflect on your business, services, and/or products. What, exactly, is your target market? Who will want to pay you for your work? Once you’ve determined that, you’ll need to pack up and head toward that target market. Many freelancers know that attending conferences in their industry are great networking events, and the same goes for your target market’s networking events. Go to conferences and open-houses that interest the people you want to work for. These are great opportunities to discover things like:

  1. Pain points in their industries; what are common problems and how can you solve them?
  2. Social cues; what will these potential clients respond well to in terms of marketing
  3. Marketing insight; what forms of marketing will put you in their line of sight?

Getting familiar with your niche falls in line with the “lean startup” mentality, which values marketing research and customer feedback as a key tool in startup success.

Learn How to Be a Marketer

I want to be perfectly clear before I go too much further here: I know that people go to school for years to become a marketing professional, and I don’t want to devalue the worth of those people’s educations. That being said, there’s no denying that freelancers and entrepreneurs are presented with the opportunity to use highly effective marketing tools that are either free or incredibly inexpensive (at least compared to traditional marketing forms, anyway).

Once you’ve done your niche snuggling, you should have a pretty solid idea about the forms of marketing that will best reach your desired audience. Now it’s time to get comfortable with those marketing outlets so that you’re confident enough make them work for you.

Social media, while being the obvious choice, should be handled with deliberate thought and strategy. Rather than going out and immediately creating an Instagram, Facebook, Twitter, Google+, and Snapchat presence because “that’s just what you do,” you need to remind yourself that your time is one of your most precious resources. If the majority of your niche doesn’t care about Snapchat, there is simply no point in wasting your valuable time by posting an update with a cute deer filter over your face.

Email marketing is another viable-but-tricky form of inexpensive marketing. Again, it’s all about your niche: how often does your target market check their email? Are they of a demographic that resents direct mail marketing? Are they going to take one look at your subject line and click “delete?”

Some forms of traditional marketing are more accessible than you might realize. Some local news stations, both radio and television, will welcome guests warmly to their morning or daytime shows, free of cost, so long as the guest can provide value to their audience.

If your target niche attends a lot of conferences, preparing a presentation or setting up a booth is a great way to get visible where it counts.

People Can Be Resources, Too

Another way to emulate the lean startup mentality is to utilize the talents of your peers to improve and expand your business. If it fits your service or product, you might consider collaborating on a service package with an admired contact in your professional network. Collaboration with another professional (whose work you respect) will benefit you in a few ways, one of which is an expansion of creativity and talent to your work. Outside influence is essential if you’re going to grow in your career, and working with another creative professional will add depth to your work.

In addition to creative enhancement, you’ll also be doubling your marketing reach in terms of both manpower and connections. Two people working to get the word out, plus the addition of your collaborator’s personal and professional network will give you a huge head start in terms of marketing.

Speaking of all the money you’re not spending on marketing… this is where you can put it to better use. If collaboration isn’t something you’re interested in, but you’d much rather focus your efforts on creating than on busy work, you can also consider outsourcing the less-fun stuff to someone else, whether it’s someone you know or a high-quality virtual assistant.

Avoid the Seat of Your Pants

Another key part of bootstrapping your business is having a plan. In order to grow and expand lucratively, you need to have points of reference and methods for analyzing your progress. One of the best ways to do this is to set up definitive goals, visit them on a regular basis, and use your progress toward those goals to analyze and adapt your strategies.

Part of this strategy (again, in line with that lean startup jazz) is to gather customer and client feedback in order to hone your packages, marketing plans, and customer interaction to be as effective as possible.

Give your business goals, work toward them, and monitor the progress in order to successfully evolve.

Don’t worry; we’ve all got bootstraps. They’re just a little hard to grab hold of sometimes.

Starting a freelance business from the ground up is intimidating, but it’s doable. If you can learn about your audience, wisely use available resources, and stick to a solid plan, you’ll be well on your way, and ahead of the game.

Plus, you’ll have plenty of ammo for that bootstrap conversation with crotchety Uncle Jasper.

You might even get to enjoy your pie.

Success!