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The Secret to be a Successful Freelancer

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The Secret to be a Successful Freelancer

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The Secret to be a Successful Freelancer

A boomer friend who recently got laid off just landed a terrific consulting gig, but is concerned that it will eat into the time he needs to spend looking for another full-time position. “Does it help or hurt to have a temporary job while looking for something permanent?” he asks.

It’s a question that concerns many folks in our generation who were accustomed to being part of an organization and have suddenly been thrust into self-employment. Job postings are written in code to discourage them from even applying – calling for at least “five years’ experience,” for example, when they have two decades more than that to offer. Some require job applicants to disclose their most recent salary, which is a Catch-22 since that information brands them as too expensive or overqualified (which can also be a euphemism for “too old”).

Though I wouldn’t discourage my friend from continuing to job hunt, the outlook is bleak. He will have to work hard to convince employers that his age is an asset, rather than a liability. And even if he succeeds in his goal, he may soon face age-based bias at the next place.

Still, he has something to celebrate: His new assignment as a consultant is a great first step toward becoming a successful freelancer. It gives him an anchor client that can provide a steady source of work and income while he hustles for other clients and continues his job hunt.

Before joining the staff of Forbes three years ago, I was happily self-employed for 23 years. (See my post, “How To Make Money Without A Job.”) For most of this time I had at least one anchor client. Each of these associations lasted between one and five years. I enjoyed most of them immensely, was generally treated with enormous respect and was free from the political infighting that plagues organizations. In fact, a colleague on staff at one nonprofit that was my client for five years occasionally commented somewhat wistfully that I had “the consultant’s halo.”

My anchor clients took a lot of the heat off being self-employed, but there were other benefits. I learned about new subjects, including some that I might never have been exposed to, and got a reputation as a quick study. I gained experience working with – and pleasing – many different kinds of people. When, for whatever reason, the gig ended, it was much easier to transition to other anchor clients that it seems to be for newly laid-off boomers to recover from getting axed and find a new job.

Unlike colleagues who have had a long tenure at a company, I didn’t expect a particular client to last forever. There were too many forces working against it: budget cuts; job mobility (or frailty) of the person who had brought me in; completion of a project; or a new business strategy that eliminated my role. So even as I was nurturing current business relationships, I was looking for new ones.

In the process, I came to view the work world as a series of opportunities – a philosophy that few job-hunters share. Often serendipitous connections led to fruitful business relationships. That positively reinforced my faith in self-employment. Don’t believe me? Here are examples of the types of anchor clients I had over the years, and some of the backstories behind them.

Special appointment. Organizations sometimes have mysterious protocols for bringing in consultants or temporary workers. I stumbled upon one of them as I was preparing to make the transition from law to journalism.

It happened at a rubber chicken lunch that I attended, hosted by my alma mater, Columbia Law School. I was still working as a lawyer, had been admitted to Columbia Journalism School and wasn’t sure how I was going to pay for it. My mentor had invited me to attend an event, where I was seated next to a fundraiser who oversaw the school’s alumni newsletter. She arrived totally frazzled because the editor had just quit. As I listened to her describe the situation, my wheels began to turn.

“What a coincidence,” I piped up in one of my gutsiest, most impromptu retorts ever. “I’ve just been admitted to the Journalism School and am looking for a job that will pay me a salary plus tuition.”

She looked at me in disbelief (so did my mentor, by the way), handed me her card, and said, “Call me tomorrow.” Within a week she had arranged for a special university appointment that I didn’t even know existed when I ponied up the idea. I would take over the job of editing the newsletter, receive a stipend equal to about half of my salary as a lawyer, get health benefits while I went to school, and not have to shell out a dime for tuition.

Technically I was a full-time student, but by occasionally writing stories that could do double duty, I was able to make my anchor client happy and still earn a master’s degree with honors. Most importantly, I learned a crucial business lesson that has served me well ever since: There are few things more powerful than being in the right place at the right time.

Contract academic jobs. In contrast to the unconventional arrangement that financed my journalism degree, many self-employed people find part-time academic work. I’ve had my share of those positions too, teaching legal writing to law students and legal reporting to journalism students. Typically these are adjunct positions that result in being grossly underpaid for your effort, but I had one for two years that was a half-time appointment, paying me half the salary and full health benefits to carry half the usual load. (Again, this was an idea I proposed, and a faculty member with hiring authority went to bat for me.)

The trouble with contract academic jobs is that, compared with colleagues who are on the tenure track, you will always be a second-class citizen. Nor will you necessarily be insulated from the palace snakes who sometimes inhabit these institutions. You will just get paid a whole lot less for dealing with them.

Consultant in lieu of full-time. Being a free agent gives you the liberty to sign on for something less than a full time job. That could make you attractive to an organization that doesn’t want to increase its headcount or is looking to cut costs. Likewise, you might be willing to accept a gig that’s perfectly palatable as an anchor client, but which you would not want as a full-time job.

Such an opportunity came my way after I wrote an article for The New York Times in 1990 about alternative dispute resolution. A nonprofit featured in the article published a monthly newsletter on the subject, and when the editor abruptly quit (yes, this was starting to look like a pattern), they called to ask if I would be interested in the job. By then I had a nice assortment of freelance clients that I didn’t want to give up. So I suggested that I be the editor, but on a consulting basis, rather than as an employee.

It was, in dispute resolution parlance, a “win-win.” They didn’t have to pay me benefits. I could count on a certain sum from them each month, and I went to their offices every Wednesday so that I could attend the weekly staff meeting. I met many interesting people; learned a lot about negotiation and conflict resolution; and honed my skills editing the work of very accomplished professionals in the field. I also worked closely with some colleagues whose friendship I still cherish.

Virtual staff. New technology enables many startups (and larger enterprises) to rely on freelance virtual teams rather than full-time employees for specific purposes. I’ve worked that way with a lot of startups. One of them was Bloomberg, before it became a large news organization.

Here’s how it happened. An editor who I had worked with extensively at another start-up called to say that Bloomberg had retained him as a consultant to help launch two new magazines. He asked me to cover estate planning for them on a freelance basis.

At the time I started writing for these magazines — Bloomberg Personal Finance and Bloomberg Wealth Manager (neither is part of Bloomberg today) – few people outside the financial community had heard of Michael Bloomberg. In fact, one prominent estate planning lawyer made a game of annoying me when I used to call to interview him, by referring to the company as Blumberg – a business that produces legal forms.

I was part of that virtual team for five years. During that time I developed an expertise about a wide range of wealth management subjects and again made many valuable contacts.

You & Co. Though many people associate anchor clients with other people’s enterprises, it’s also possible to start a company of your own and turn it into an anchor client for yourself and others. I did that when I decided to self-publish my book, Estate Planning Smarts in 2009. (See my post, “How My Book Became A (Self-Published) Best Seller.”) At a time when big publishers were cutting experienced staff, I retained top talent for editing, graphics, production and web design – on a freelance basis. This virtual team has been a very loyal and reliable support system through three editions of my book.

For people accustomed to a steady job, having a series of anchor clients may sound like being adrift in a sea of uncertainty. But there are no guarantees in corporate life these days either. Whether we are self-employed by choice or circumstance, a world of possibilities awaits.

Archive of Forbes Articles By Deborah Jacobs


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Update: 2

Two Views of Independent Work in the Sharing Economy

Source: Small Business Labs

Two articles with very different points of view on work in the sharing economy were published this weekend. The New York Times article In the Sharing Economy, Workers Find Both Freedom and Uncertainty presents an unflattering view. Key quote: ... peer marketplaces as part of a larger global phenomenon, in which labor brokers encourage people to work on contingency without basic employment benefits or protections. T ...
Source: Small Business Labs   Full article at: Small Business Labs 5 days ago, 3:00am CDT


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