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?

20 thoughts on “The other skills you need for successful self-employment

  1. The first impression thing is so powerful. I broke out in a flop sweat in the middle of my last interview, it was ghastly! The interviewer couldn’t have but noticed. Thankfully they were discreet and luckily however else I conducted myself did the trick because I start the job next week. I’m pinching myself!

    1. I think we self-select into those happier working on their own, finding clients (and living less securely) and those who really want the structure of a “real” job in an office or organization. Having done both, I enjoy elements of both.

  2. I am going to try my hand at self-employment, and this post is encouraging. My strongest asset seems to be my network. I never thought of freelance being a gig spent in monastical solitude. (Or, keep dating!) My only worry at this point is hooking the first gig….and taxes.

    1. Some people rent an office or a co-working space to have some other people around them; I’ve been too cheap to spend the $300 a month although I’m now starting to consider it even a few months at a time as a break from the isolation.

      Your network is really important. The first gig might be tough because until you have clips (written, published work) you don’t have proof you can do it well. Taxes are the least of it.

    1. Very true.

      The ideal is to have every client become a repeat for years, but sometimes the fit is very poor and you make the choice never to work with them again. That happened to me this year with a promising new client.

  3. Good question! Trying to pick the most essential skill according to my experience… I think it is the ability to “see” a community of like-minded clients out there, even this is not an obvious target group described in an article by a marketing expert.
    I think you need to define your target group as precisely as possible (probably you do this intuitively). In IT my target audience comprised “geeky system administrators” – the common sense of humor really was the most important criterion.

    1. Ohhhhh…so cool! Thanks for this.

      It’s very true, that if I only defined my market as print journalism (and some do), it’s too narrow for me, intellectually and financially. Instead, I think many people are very hungry to learn to discern and tell compelling stories…in business, academia, NGOs, etc. I’m a professional story-teller so I need to find them, wherever they are. I like your POV.

      And so interesting that humor is the link. In journalism, it’s probably a hard-boiled way of seeing the world.

  4. Great advice, as usual, and all noted. Knowing how to ask for advice is not something that comes naturally to some of us. I’ve often found it’s easier to ask on behalf of someone else than for myself (go figure). It’s also smart to recognize, respect and prepare for the fact that there’s a lot more that goes into freelancing than meets the eye.

    1. Similarly, I’m much better at promoting others’ work than my own. I’m not sure what my strongest assets are because it’s hard for me to identify them. I’m much better at finding what I did wrong or need to improve. There’s a thin line between being honest with yourself and beating yourself up. 🙂

      1. Ouch! I think that’s sadly fairly common.

        One thing I found helpful in this respect was investing some $$$ in aptitude and career-focused tests; I found (or confirmed) that I am highly creative (98th percentile), decisive and logical. Those are all good things (and skills) I had never even considered as such. An objective outside perspective can be surprisingly helpful and insightful.

  5. I’ve only been freelancing last August and I’ve worked on quite a few projects with my client continuously. Communication skills are definitely important. I reckon it’s also important to show that I’m responsible and reliable towards my client. At the start, I was asked to work on-site. But after a couple of months I was given the green light to work off-site. I still take the opportunity to work on-site so that my client is aware of the work I’m doing and it’s also a good way to build a relationship since we see each other at the office a few days a week.

  6. I’m new to freelancing, and to this career, so I’m learning a lot and grateful for this advice. Thank you very much for this. I confess though, I’m now nervous about asking for advice, especially with money as tight as it is for me. I can probably afford to buy someone a cup of coffee, but that’s probably about the extent of it. But I guess that’s better than nothing.

    Speaking of advice, and business cards, I’m trying to build a good website, and I think I have a business card I like, but I’d love to hear your thoughts on what exactly a “well-designed” business card and website is, if you’re willing to share. Thanks!

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