The other skills you need for successful self-employment

By Caitlin Kelly

People who choose self-employment often focus on the freedom — No office! No boss! No politics! No commute!

Freelancers Union Logo
Freelancers Union Logo (Photo credit: Wikipedia)

But successfully running your own show requires a wide range of skills beyond the specific product or service — dog-walking, gluten-free cupcakes, general contracting, writing — you’re hoping to sell.

Here’s a great post from one of my favorite blogs, Freelance Folder, on this topic, which lists 17 separate skills with a link to even more:

Communication skills. Freelancing is all about clear communication. As a freelancer, you must express your ideas and requirements to prospective clients, current clients, and other freelancers.

The first one can be a real toughie.

Once you’ve established a good working relationship, and a track record, with your clients, you’re usually good to go. You probably speak the same language, emotionally, so you click naturally in your communication style.

But to steadily earn a good living will also mean working with many people quite different in their style.

Would-be clients are busy with competing demands and may not communicate quickly, clearly — or at all! I see many emails from fellow freelancers asking when, if and how often to follow up with a pitched idea so we can close the sale (or not), find out the fee and budget our time for the work and the income for our expenses.

Follow up too often and you’re a stalker. Not often enough and you’ll starve because you can’t keep enough work coming in.

Whenever I start working with a new client, I ask a few questions about their communication style: do they prefer phone or email? Are specific days or hours in the day off-limits? How long, typically, does a pitch take to get approved?

When I work with The New York Times — which is almost weekly — I know from experience that my emails often end up in their spam filter due to my email address. So I know to call and leave a voicemail message to follow up.

Estimating skills. How long will a project take? Successful freelancers need to be able to answer this question so that they can schedule their time effectively and still earn a profit.

This is also a difficult one, no matter what you do for a living.

I recently blogged about knowing your CODB, your cost of doing business. So you know what you must make to cover your expenses — but what about short and long-term savings, retirement savings, attending a few conferences every year to upgrade your skills and meet new contacts?

Illustration from "Living Up to Your Empl...
Illustration from “Living Up to Your Employment System” (Photo credit: Wikipedia)

So when someone quotes you a price, or vice versa, never forget all those other costs, not just the short-term gain of that payment.

The challenge of estimating is that it’s one-sided! We know how long we might need to do the work…but what about your client?

Does the work require reviews/edits/approval from several other people? How long will that take? (Can you negotiate partial payment up front?) Are they known in the industry as challenging or difficult?

Ask around so your “estimate” isn’t naively and stupidly optimistic.

Interpersonal skills. The stereotype is that freelancers work alone and don’t need interpersonal skills, but that’s a myth. Freelancers interact with prospects, clients, and other freelancers.

Oddly enough, this might be the most essential skill of all. The (mis) perception of freelance or self-employed people is that we “don’t play well with others.” Which isn’t true at all — if we didn’t, we’d never find or retain satisfied clients!

From the very start of your freelance life, you’re going to need other people to help you: for advice, insight, feedback, moral support, sometimes a shoulder to cry on or to toast your latest coup. Almost every single day, by phone, email or social media, I’m asking for, or giving, advice to someone.

At this point in my career, 30 years into it, virtually all my work comes from established clients or personal referrals to new ones from people they know, like and trust.

So play nicely, ladies and gentlemen! Never steal ideas, backbite, gossip.

And don’t be nasty, even if you’re feeling really shaky and insecure.

Networking Freelancers
Networking Freelancers (Photo credit: solobasssteve)

So, go out often — at least once every month — to industry parties and events and panels and conferences. Bring a genuine smile, a well-designed business card and a generous spirit.

And look professional! At a recent NYC roof-top event I attended, a woman around my age was wearing chipped red nail polish. Seriously? You need a great/recent haircut (and/or color), polished shoes, fresh mani/pedi (do it yourself, but do it!)

We make snap decisions about people within seconds of meeting one another. Make sure they’re positive.

Do not — I beg you — use the phrase “I’d love to pick your brain”. Ever!

Of course you would.

You think it’s flattering. It’s not, really. Because our brains are already spoken for. Instead, be classy: offer to pay us a consulting fee, make a useful professional introduction or buy us a good meal. Don’t be cheap and assume it’s our job to mentor you because you’re needy. It’s not!

And don’t become the whiny/negative/raggedy/sloppy person whose calls we dodge and emails we delete.

If you’re self-employed, what skills do you find most essential to your success?