Chapter 3

YOUR FREELANCE PORTFOLIO

Freelancers can’t count on paychecks, promotions, or job titles as benchmarks for their value. They have to create their value in the marketplace every day.

I’ve talked with thousands of freelancers. Nearly all say variable income in a world of regular expenses is their biggest stressor: “I keep a certain amount in the bank. If it drops below that amount, I’ll consider returning to corporate America. So far it hasn’t, but it’s getting very close, and I’m more worried than usual. It’s not good for me.” But there’s a flip side. Not to minimize the challenges, but one freelancer astutely commented, “I think the danger in freelancing is that we can easily condition ourselves to struggle.”

You can think of freelancing as volatile and risky, or as flexible and opportunity-rich. Doesn’t having multiple sources of income and multiple moneymaking skills sound less risky than putting all your eggs in an employer’s basket? It’s no accident that during the 2008 recession, Nebraska had one of the nation’s lowest unemployment rates (4.8 percent), partly because many Nebraskans held more than one job (a farmer might also do equipment repair).

Freelancing lets you shift gears when the world does.

When you look at freelancing that way, the question becomes not “How can I keep the ups and downs from happening?” but “How can I ride the waves?” Enter the Freelance Portfolio.

THE FREELANCE PORTFOLIO

A Freelance Portfolio is similar to a financial portfolio. A financial portfolio spreads your money across multiple investments with varying levels of risk and return. The goal is to diversify your holdings to provide maximum income while protecting you from the market’s volatility: When one investment’s down, another’s up; some are low-return/low-risk; some are higher-return/higher-risk, and so on.

Your Freelance Portfolio helps you balance the risks and rewards of your freelance life. It helps you weigh how much time and energy to “invest” in projects, and change the mix depending on the work market and your income needs. It lets you decide how work fits into your plans, not the other way around.

The Freelance Portfolio has four levels, explained in more detail below:

Level 1 | The Blue Chips

Level 2 | Growth Investments

Level 3 | One-Shots and Long Shots

Level 4 | New Ventures and Growth

You want to balance these levels so your Freelance Portfolio meets these three goals:

Goal 1 | Have enough clients of the right kind: not too few and not more than you can handle, who pay well and/or can advance your career in some way.

Goal 2 | Bring in enough steady income to reduce cash flow highs and lows.

Goal 3 | Meet your total income goals.

LIFE IN THE BALANCED LANE

What does a balanced Freelance Portfolio look like? Here’s what it doesn’t look like (and what you can do about it):

Imbalance: Your pipeline’s full, you’re working like crazy, but barely making ends meet.

Rebalance: Reassess your portfolio for Goal 1.

Imbalance: You’re making a decent income, but the payments are so far apart you struggle to meet your monthly expenses.

Rebalance: Focus on Goals 1 and 2.

Imbalance: You’ve got some great clients and gigs, but the money’s lousy.

Rebalance: Retuning all three goals may be necessary.

Portfolio planning isn’t just about how busy you are, but about finding a client mix that delivers maximum value for your time and effort. This boils down to a handy equation:

optimal clients + steady cash flow + meeting your income goals = balanced freelance portfolio

Here are the benefits of a balanced Freelance Portfolio:

No more living project-to-project. Changeable schedules are part of freelance life: “Project schedules inevitably shift and collide, so some weeks are insane with work and others are very quiet. If you averaged it out, it would probably look something like a normal workload, but it never feels that way!”

When these fits and starts happen to a freelancer with a balanced portfolio, other prospects and possibilities are quietly simmering. If a project gets back-burnered or a client pays late or fades away, you’re more likely to be able to quickly turn up the heat and land a gig or two to fill the gap.

No more “pipeline perspective.” A full pipeline’s only as good as the projects in it. Your portfolio lets you weigh your projects and craft a mix that serves your income goals.

No more “Oops, forgot to network.” “If you don’t divide your time between looking for new work and doing your current work, you’ll finish your project and be tearing your hair because you don’t have any work lined up.” Your portfolio lets you track your workload, anticipate quiet periods, and ramp up your marketing. There may still be dry times, but odds are they’ll be fewer and shorter.

No more “fire, ready, aim.” Your portfolio lets you see holes and change your goals—whether it’s landing or replacing a Blue Chip, growing your network, increasing your cash flow, or building your future with new products or services.

Let’s look at each level in more detail. At the end of the chapter is a template for making your own Freelance Portfolio.

LEVEL 1: THE BLUE CHIPS

WHAT THEY ARE

Your Blue Chips are the core of your Freelance Portfolio. Like blue-chip stocks, they’re your buy-and-hold investments: major clients (large or small in size) that you maintain and monitor carefully as sources of regular income.

WHAT’S TO LIKE

Income anchors. Blue Chips are your hedges against marketplace rock-and-roll. They keep the lights on. They are your priority.

Rich relationships. A positive Blue Chip relationship can be rewarding on every level. You get to know and respect one another as professionals and people. Your work together deepens and sharpens. It’s satisfying, lucrative, and just plain nice. Holiday cards and treats may be exchanged.

Referrals. You’ll likely get referrals, or if your contacts move to other companies, they may seed new Blue Chips.

WHAT’S CHALLENGING

Systems and shifts. You might be at the mercy of corporate bureaucracy and politics: glacial payment schedules and protocols, projects scrapped or delayed at the whim of the suits. If they’re small companies, you may be buffeted by their fitful cash flow or changing strategies in their struggle for market traction.

Great project, awful people. You may have to suck it up until you can groom another Blue Chip.

Great people, awful project. See above.

Poof! Like anything else in business, Blue Chip gigs can disappear overnight: “Due to the economy, the company where I had a major consulting contract made some big cuts. Mine was one of the accounts that got cut. Even when you have a great relationship, sometimes the situation’s out of their hands.”

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COMMUNITY ALERT

LOVE THEORY AND YOUR FREELANCE PORTFOLIO

Just signed a new Blue Chip and overwhelmed with work? Subcontract! Hack that gig into pieces and contract a fellow freelancer (or several) to do portions under your supervision. Get someone good at time-consuming tasks like transcribing or photo research, or someone starting out who needs experience and mentoring. Make sure your agreement specifies that you’re the intermediary with the client and they can’t go around you to be hired directly. Talk to your accountant to make sure you comply with tax requirements when subcontracting. (For more on subcontracting, see Chapters 11 and 15.)

Of course, you’d never subcontract to someone you don’t trust. You build trust through relationship. You build relationship by giving—info, help, and (eventually, with trust) shared work. That’s Love Banking. These relationships aren’t business transactions so much as the outgrowth of how you choose to live your life, working and playing with lots of people you enjoy and care about.

Speaking of subcontracting, you can have Blue Chips as a subcontractor, too. Maybe there’s a sole proprietor who needs to offer services like yours. It’s a great strategy for regular cash flow if repeat clients aren’t common in your type of work, or if you hate prospecting: Someone else gathers the pollen; you’re the worker bee.

BALANCING BLUE CHIPS

Have more than one. So if you lose one, you’ve got at least one other.

Keep Level 2 prospects simmering. You can get lulled into a comfortable place with Blue Chips (see “Poof!” above). Cultivating Level 2 prospects keeps you nimble. Can’t stand a particular Blue Chip? Don’t get mad; get a new one and phase out the old (or raise your rates to make them worth the aggravation).

Remember boundaries. Sometimes you’ll go the extra mile for a Blue Chip, letting a project bulge out of scope. Be friendly but clear that this is a sometimes thing, so everyone’s expectations stay in line. With tough Blue Chips, boundaries are essential. You shouldn’t tolerate what the staff has to put up with to keep their jobs.

LEVEL 2: GROWTH INVESTMENTS

WHAT THEY ARE

Level 2 is the growing edge of your business and your Blue Chip incubator. The gigs turn over faster than Level 1 and generate income by their volume while enriching your client base. The more you nurture Level 2, the more it can stabilize your career.

You’ll get Level 2s from client referrals, other freelancers, and your own prospecting, so it’s about networking. While not every lead pans out, over time, as you expand and refine your strategy and bring in more and more projects, most of which bring good revenue or referrals for more work, your net return will be positive.

WHAT’S TO LIKE

You’re in control. You decide what prospects to pursue and how you want to be viewed. It’s you saying, “This is what I do, and how my work can help you.” Way more powerful than, “Tell me what you need and I’ll do it.” The business world not only expects people to communicate their value clearly, but rewards it.

Nice and smart. Level 2 is where profitable opportunities are born. Example: You spot an opportunity that more specialized company workers don’t see. You bring it to a client with whom you’ve worked well. Of course, you suggest how you could help make it happen, with just enough detail to show how big you could deliver. Suddenly, you’ve got a new gig. But even if not, you’ve made a huge impression (how many of their employees are this proactive?) and just moved to the front of the line for the next time they need outside help. Nice. And smart.

WHAT’S CHALLENGING

Juggling. When Level 2 gets rolling, you’ll have lots going on. This is the beating heart of freelancing. Make sure you have love banked in case you need a hand, a favor, or advice from a fellow freelancer.

Hitting your stride with networking. Reputation and word of mouth will only take you so far: “I had a track record and initially built a clientele from that. But I didn’t promote myself. I’m a private, retiring person and never thought about marketing myself. I was under the misassumption that people knew my name.” Everyone can network successfully. It’s about finding the approach that works for you and brings you the level of projects you want. We’ll talk about finding your own networking style and get into specifics in later chapters.

BALANCING LEVEL 2

Price to compete. In Level 2, you want to price yourself high enough to weed out low-paying, time-suck gigs, but not so high that good prospects assume they can’t afford you (such as a promising start-up that could become a Blue Chip, or a high-visibility, lower-budget nonprofit). It might help to itemize pricing on some components of your work. An à la carte approach might make you affordable to a wider market without lowering your price.

Persist, persist (did I say persist?). “I get work because I put it out there and put it out there and put it out there and put it out there some more. I just keep knocking on doors. That, combined with the fact that I’m friendly and likeable—and talented—gets me work.”

. . . but be selective. Trust your gut. If you sense a prospect will cost more to keep than lose—haggling over nothing, making constant changes, expecting way more than they’re paying for—find other prospects worth working hard for. You’ll be happier, more productive, and in the long run probably no worse off in the pocketbook.

LEVEL 3: ONE-SHOTS AND LONG SHOTS

WHAT THEY ARE

These are opportunistic gigs that fill time or income gaps (as in “I need money now!”) or let you make the gig-getting aspects of freelancing more plug-and-play. I group sources of Level 3 gigs into two categories:

1 Passive intermediaries, or what I call “listers.” These sources list available jobs and leave the rest of the process up to you and the client. They include print classifieds, online job boards such as Craigslist, Monster, Freelancers Union, and MediaBistro, and professional association job board listings.

2 Active intermediaries. These entities more actively manage the freelancer/work provider relationship; for example, by handling payment, instituting systems for communication or workflow, or providing some benefits. Temp and staffing agencies are in this category. So are work exchanges: on-demand workforce websites that have proliferated alongside the expanding freelance workforce as companies trim staff and start-ups can’t afford to hire, but both need work done.

Put simply (and ideally), independent contractors post their profiles; work providers post their projects; the twain meet to their mutual benefit, while the host website oversees payment and facilitates interactions for a fee. Some examples as of this writing include Elance, oDesk, and Guru.com.

Both categories are useful in aggregating projects in one place. So—duh!—everyone’s cruising them. Check them often enough to stay current, grab a good gig, or mobilize fast for cash, but you shouldn’t spend a lot of time trolling these über-competitive spaces. Especially in the case of work exchanges or staffing agency jobs, the pay rarely warrants it.

WHAT’S TO LIKE

Opportunities at a glance. As mentioned, these sources aggregate leads for quick scanning and comparison shopping.

No cold calls or networking. Prospects are looking to hear from you—one reason why it’s easy to get sucked into online gig-hunting at the expense of networking.

Easy application. If your résumé or application materials are ready to go or if your profile’s posted, you can move fast.

Supplemental income, seasoning, and selection. Work exchanges can be handy for picking up work in a pinch or supplementing your income. They’re also useful if you’re new to your industry, new to networking, are returning after a break, or want to control your workload—for example, there’s a new baby at home, you’re job-hunting, or anytime you want or need more short-term, self-contained projects.

With work exchange sites, no chasing payment. These sites advertise project approval, systems to ensure payment if you meet the work provider’s benchmarks, and protocols for disputes. While there are no guarantees of a smooth ride, these safeguards can reduce the risk of working with an entity you don’t know.

You might find some Blue Chips. This shouldn’t be your rationale for trolling these sources, though.

WHAT’S CHALLENGING

Welcome to the cattle call. You may not be networking, but you are auditioning. Applying for these gigs can feel like a Broadway casting call where hundreds wait for hours in the rain to tap dance for thirty seconds, and a handful make the cut.

Checking in, or checking up? While technology can help workers and clients find each other, it also allows more monitoring of workers’ performance. Work exchange websites have systems that electronically track freelancers’ progress and hours as part of managing projects long-distance and ensuring payment for work completed. Some call it transparency; others call it an intrusion that takes the “independent” out of independent contractor and veers unacceptably close to the kinds of oversight employers are entitled to exercise over employees—but without the benefits employees are entitled to in return. Employers can’t have their cake and eat it, too: getting a capable “on-demand” workforce free of the obligation to provide any benefits, yet with the power to limit their work product and freedom as if they were employees.

Beware of bargain-basement pricing. The pricing on job boards is hugely variable. On work exchanges, it’s generally low. Since you’re competing with a global talent pool, a) you’ll spend time applying for positions with less chance of getting them, and b) prices are pushed down when the labor supply exceeds demand. That’s why I recommend that you not put all your eggs in the Level 3 basket. Remember the mantra of the balanced Freelance Portfolio: a client mix that delivers maximum value for your time and effort.

If you need income, you do what you gotta do. Otherwise, consider whether you’d be better off working Level 2 and holding out for quality over quantity in your portfolio.

Remember, too, that as a freelancer you have the option to work outside your usual frame. For example, one of the sample Key Skills lists in Chapter 1 listed “math tutor” alongside sophisticated accounting skills. Maybe that freelancer would think, “I’m not getting any enjoyment, new skills, or reputation value from these Level 3 gigs. For the same pay, I could pick up some math tutoring, which I love doing. Plus, I can do that during off-hours and still have time to look for other work.” Freelancing gives you that flexibility; staff jobs don’t.

Here’s another reason to be leery of bargain-basement pricing. When companies can choose from a giant pool of available talent responding to online work listings, it drives prices to artificial lows that don’t reflect the true value of the skill required for the work. Freelancers’ main strategy has to be increasing economic power so as not to be dependent on getting work online. Freelancers need to think twice before taking bottom-feeder jobs and hold the standard for higher value to be placed on their work. We also need to build freelancers’ political power to make sure the practices on work exchange sites are fair.

BALANCING LEVEL 3

See Level 3s for what they are: ways to get short-term gigs, work experience, or quick/incremental/supplemental income—not as your primary income source.

Limit trolling time. The time you invest should be in proportion to the income potential. Level 3 shouldn’t be mined at the expense of Level 2.

Ask your Brain Trust and other freelancers if they’ve gotten work this way. What was it like for them? How did they make it work?

Look for the three Ps: price, projects, and people. Focus on higher-paying, higher-quality projects that will boost your skills or credits, and for clients you feel you’ll work well with. Their positive testimonials will boost your earning potential. And they may become Level 2 or Blue Chip clients.

Focus on specific kinds of projects. Once again, a specialty helps.

Be clear on payment procedures, oversight, and dispute policies. Are you paid by the hour or getting a fixed price? How are payments triggered? Exactly how do the oversight and dispute policies work?

Make sure the project description, directions, and deliverables are well defined. If not, ask. A good outcome is in everyone’s interest. Showing you want to get it right impresses clients, too.

Bring your best game. Take the tests and ace them. Tailor your pitches to the projects. Get great testimonials. That’s how these sites work, so make them work for you.

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ASK SARA

Q Dear Sara, What about temping?

A I’d put temp or staffing agencies at Level 3. These agencies match workers with employers needing particular skills, in exchange for a fee from the employer or a percentage of the worker’s salary. It used to be that you’d register with one agency and become eligible for benefits by accruing hours. Now, it’s usually necessary to register with multiple agencies to make ends meet, reducing the likelihood of accruing enough hours though one agency to be eligible for benefits.

Upside: Someone else finds the gig and handles payment and administration, while you have a chance to make a good impression on the employer, which might lead to future gigs.

Downside: not much choice in the work, and lower pay.

Getting work through an agency can be useful during a long dry spell or if you need experience: “I know I’m very good at what I do, but I couldn’t point to multiple-year experience. When I set out as a freelancer, I networked as best I could. And when I couldn’t get any new assignments, I got temp jobs doing administrative support until I could get work.”

LEVEL 4: NEW VENTURES AND GROWTH

Level 4 is in some ways the most speculative part of your Freelance Portfolio, but it’s also the most exciting. Here, you’re building the services, products, and alliances that will bring income in the long-term future.

These are ventures you’re creating on your own or with others: developing a seminar, pursuing speaking gigs, teaching classes, writing a book, collaborating to offer expanded services. You might test-drive them for free or use them as “freemiums” to build your profile, but the ultimate aim is to position you for a profitable future. As one freelancer said, “A huge factor in my staying in business was that I’ve reinvented myself many times while staying in the same industry. To be on your own you have to generate ideas, and you have to see where the market will be a few years from now.”

Level 4 ventures need to be phased and planned so they stay on your radar but don’t take over and cut into the time you need to make your living. We’ll talk more about them in later chapters, but here are some ways to cultivate Level 4 no matter how busy you are:

Don’t set yearly goals. At least, not the “set and forget” way most people do. Instead, set yearly goals and then make a monthly, even weekly, breakdown of small, achievable steps to get there.

For example, if your goal is to lead seminars but you’ve never spoken in public, steps might include reading books on public speaking; taking a class on speaking; volunteering for public roles in your professional organization, your kids’ school, or in your community or spiritual group; attending seminars and asking the speakers afterward how they plan their events; outlining a topic for a short talk about your profession, then pitching and giving the talk; et cetera.

Take steps, not leaps. Shuffle if necessary. One goal achieved is better than many unmet. Very small steps make for steady progress, which motivates you and helps you correct your course as you go. To take the seminar example above, if that seems like too much to do in a year, set a goal to read some books and take a class.

Put each step in your calendar. Just do it, even if it’s “Make a list of steps.”

Treat yourself like a client. Treat Level 4 projects as you’d treat a project: Break it down, identify trouble spots, set up a schedule, project-manage it.

“DRY TIME”—WHAT TO DO WHEN NOTHING’S COMING IN

A short dry spell after a busy period can be a luxurious chance to sleep in, get back to the gym, and catch up on filing. But when you’re spending half a morning swabbing grunge off your keyboard . . . not so fun. Not just because no money’s coming in, but because freelancers like to have stuff to do. If they wanted to spend time perfecting how to say “Not my job,” they’d be trolling for company positions.

Dry time bites when you lose a Blue Chip and get caught with your network down. Or when one bleh thing happens after another: A project’s postponed, another’s canceled in a budget cut, a client pays late, and prospects you were certain would lead to gigs don’t.

Dry time is a tough reality for freelancers. Our 2011 survey showed that:

• 79 percent of independent workers surveyed didn’t have enough work in the last year (2010).

• 49 percent experienced periods with no work, with an average of fifteen weeks without any work.

Of those who had trouble finding work:

• 35 percent dipped into savings intended for other purposes (such as retirement).

• 35 percent used credit cards.

• 3 percent had to rely on some form of government assistance.

FOUR BENEFITS OF DRY TIME

Benefit 1: Dry Time Pushes You to Do “The Ask.”

There’s no shame in asking for work. You’re letting people know your skills are available. Try something like . . .

“Hi. I finished that big project and am open for new work, so if you hear of anyone who needs online marketing, I hope you’ll recommend me or let me know. And now we can finally meet for coffee and catch up! When’s a good time?”

“Dear Ms. Major: Sam Prescott at X Corp. recommended I contact you. Sam and I worked on several online marketing projects together. I develop social media campaigns and have had particular success with [pertinent example]. I’d like to set up a brief call or meeting to learn more about Major Productions and whether there are ways I might be able to help. I’ve attached some information about my work . . . [et cetera].”

“Hi, Jane. It was great meeting you at the school Halloween party and talking briefly about your company, Major Productions. As I mentioned, I develop social media campaigns and have worked with X Corp. and others. I’ve had particular success with [pertinent example]. I’d love to have a short call or meeting to learn more about Major Productions and whether there are ways I might be able to help. I’ve attached some information about my work. When would be a good time for you?”

“Hey—just wanted to let you know I’ve got some open time, so if you hear of work or if there’s something you’d like to subcontract out, I’m in the market. Thanks!”

Benefit 2: Dry Time Reminds You That Work Can Come from Anywhere.

“Last month was my slowest month so far. And it came on the heels of an expensive home repair. After some financial hand-wringing, in desperation, I reached out to two contacts that had cooled a bit. With one, I asked—in my best nondesperate tone—if he had any work. He did! It’s good work, pays well, and has a quick turnaround. The second contact was happy to hear from me, and we set up a meeting for this week to catch up. He has national clients and a great reputation. Now I have a wildly busy six weeks ahead of me.”

Benefit 3: Dry Time Reminds You to Tend Your Portfolio.

“I’ve been freelancing for less than a year, and I really haven’t created any long-term schedule. I’ve been lucky to get work just in time to get my bills paid. Hitting a slow time made me think more about planning, strategy, and diversifying my client list. And frankly, I think I need to work harder when I have the chance. I’ve skated a bit, and it’s come back to bite me. I have to keep my motivation up.”

Benefit 4: Prolonged Dry Time May Point to Market Changes.

Working all the levels of your portfolio and still long time, no gigs? Maybe market demand is changing. Do you need to add new skills to your bag of tricks? Seek clients in a broader range of businesses? Make alliances to expand your offerings? Temp or do virtual assistant work while you retool? Talk to your Brain Trust: “Is it the market? Is it me?” This is your time of need, so be sure you give back to those who help with insights, advice, or leads.

THIRTEEN TACTICS FOR DRY TIME DAMAGE CONTROL

1 Keep a routine. Treat your work days like any other, but you’re the project: touching base with former clients and potential Blue Chips (Level 1), prospecting, cold-calling, seeking referrals, following up with new contacts, going to events where you can network (all Level 2), and checking job boards and work exchanges (Level 3). Save time by creating several form pitch letters you can customize (like several of the “ask” letters in Benefit 1).

2 Connect. Not only because you never know where the next gig might come from, but because de-isolation reduces the loneliness of dry time.

3 Tidy up. Tackle the administrative stuff you’ve been meaning to get to.

4 Ask for testimonials from satisfied clients. Say you’re working on your website or updating your professional profile online and would appreciate being able to post a testimonial.

5 Clean up your act online. If you find things a prospect might misunderstand or find objectionable in your social media activity, modify or delete them. Update your bio across platforms. Add recent accomplishments, awards, testimonials, or other achievements. Is it clear what your specialties are? Is it clear what value you deliver? Is it clear what clients are likely to benefit from your work?

6 Evaluate your business model. Dry time’s more stressful if you suspect you’ve been undercharging. Research where your fees fall on the spectrum for your profession. Are there some tasks you’ve subcontracted that you can do yourself? Have your business and personal spending crept up? Setting up consistent bookkeeping and budgeting systems can help you track and compare—see Chapters 14 and 17.

7 Add skills. Take online tutorials or get coaching from a fellow freelancer. If you can afford it, enroll in a course or certification program that’ll add to your marketability (then update your bio!). Visit blogs and websites for insights and advice about your industry, marketing tips, financial planning info, and productivity strategies. Books on all these abound—your library’s a free resource.

8 Consider bartering. Sometimes when money’s tight, a friend or fellow freelancer will do you a favor by offering their free expertise—maybe making some fixes on your website. And you’ll return the favor—maybe helping them set up a better accounting system. If you barter services, know that it carries tax implications (you’re receiving value that should be reported) and check your accountant before getting into any serious bartering (for additional info, see Chapters 11 and 15).

9 Do pro bono or volunteer work. It feels great, and you’ll find new friends, connections, and community. Maybe it’ll lead to some work, that’s not the point. Connecting is intrinsically good.

10 Make dry time “you time.” If your business has predictable slow periods (post-holidays, post-taxes, post-wedding season, post-school year), prepare a financial cushion during your busy time so you can take that down time for rest and personal development: your vacation, a class, or anything you want. Planned dry time keeps it from being so dry.

11 Work Level 4. Step up your brainstorming and development of new income ideas (more on this in Chapter 10). Deepen your social networking: Start or get back to your blog; add contacts, connections, friends, and followers (for ideas, check Chapter 9). Remember all the times work came from unexpected places. You truly never know where your efforts will lead.

12 Revisit your Key Skills List. Are you using them all? Are there some you can add? Look at the whole you. Serious knitter? Start a knitting instruction group. Serious swimmer? Take lifeguard training and bring in some summertime cash. Great with a specific kind of software? Get gigs teaching it.

13 Be scrappy. If you take absurdly low-paying gigs for a while because you really need the money, so what? If you take temp jobs, work in a café, or do handyman work for a while, so what? You’re making a living. That’s what counts.

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ADVOCACY ALERT

UNEMPLOYMENT INSURANCE FOR INDEPENDENT WORKERS

The unemployment insurance system was set up in 1935 to ensure economic stability and protect employers and employees from financial devastation in economic downturns. Basically, employers pay payroll taxes into a fund administered by the federal and state governments. They can then lay off workers when necessary and (theoretically) rehire them in better times, and workers can weather layoffs by drawing on the money while they look for work, rather than depleting savings or accruing debt.

Recent downturns have strained this system, and its power to protect the economy will only weaken as the independent workforce grows. Freelancers Union is advocating for reforms. Self-employed workers should be able to contribute pretax dollars each year to build their own financial cushion to draw on during unemployment. So-called “permalancers” or “permatemps”—people who work long-term for one employer doing work very similar to permanent employees but who are denied employee status and benefits—need easier recourse to prove their eligibility for unemployment, and temp and part-time workers need easier access to this protection. Dry time may never be stress-free, but freelancers shouldn’t be forced to live perilously close to the edge financially as a matter of course.

WORKING FOR FREE: SHOULD YOU?

The answer is “it depends”—on whether you can afford it, have the time, are looking to build connections, develop experience, or just plain want to: “I work for free when it’s for a good cause, like a friend’s start-up publication or contribution work for a nonprofit organization I care about.”

Working for free can help you build experience and a body of work: “I often tell my students this is how they can get some of their best portfolio pieces—it’s proven to be the case for me.”

Doing pro bono work during dry time keeps you sharp and busy—and nothing attracts business like a busy person: “It helps to be busy. Then prospective clients know other people are using your talents.” (P.S. You don’t have to tell them you’re working pro bono.)

Doing a self-contained task gratis can be good business. It showcases your chops, builds goodwill, potential word of mouth, and, maybe, the possibility of pay for more. Pro bono work for nonprofits is rewarding and may bring recognition and referrals in time. And if nothing comes of it, that comes with the territory: “You exchange thoughtful emails for a while with a client, hoping it’ll turn into a marvelous project. Nine times out of ten, it doesn’t.”

If you work for free, I believe you have to do it with no expectation of anything other than the satisfaction of your contribution. That’s a personal decision: “I’ve learned not to work for free. When I was starting my agency, I worked with a writer on a book concept. Every week we’d work on it, and every week he’d start over. After months of banging my head against the wall with nothing to show for it, one of us realized we had two separate ideas. I’m not sure I got much from this except frustration and migraines.” Also, sometimes people value what they pay for: “I’ve done appearances for free, but I didn’t find it successful. I was showing up and no one knew I was coming. Now I charge a fee, and when I arrive it’s a big deal.”

Be cautious before accepting goods in lieu of payment. Not only are there tax issues with bartering, as mentioned, but there are times when there’s no substitute for cold, hard cash: “One client wanted to pay me with a gorgeous, drop-dead outfit. I wavered and then realized that as lovely as the outfit was, I had no place to wear such a beauty. It was a good thing I said no and wanted cash. As I drove home, my car died. I managed to pull to the curb, and as I was calling the mechanic (who had just repaired it!) a passerby said, ‘Hey, lady, your car’s on fire!’ I ran to a safe distance and called the fire department. The money owed that day went for a down payment on a new car.”

When it comes to doing good in the community, freelancers have a special opportunity to put their skills to use. An accountant in a corporation may crunch numbers all week and volunteer in a soup kitchen on weekends. Very admirable, but somewhat segmented. A freelance accountant may be able to put in a few hours a week doing the books for a fledgling nonprofit that desperately needs accounting help. The income’s tiny or nonexistent, but there’s something hugely gratifying about discovering your skills really matter; in fact, they make a survival difference to that organization. As a freelancer, you can ply your trade for whomever you choose—for no other reason than that it matters to you.

Thinking back to the freelancer whose comment opened this chapter, I’m reminded of the two sides of freelancing: the freedom of it, and the responsibility of it. They’re really two sides of the same coin, and the Freelance Portfolio unites them. OK, so you don’t have a staff job and can’t do your work with one hand, check the sports scores with the other, and still pull down a regular paycheck. But you’re no office drudge waiting for the weekend, retirement, the axe, or permission to take time off. Instead of checking the scores, you can decide to take the day off and go to the game. Instead of waiting for the weekend, you can start your weekend any day of the week. You can rearrange your life to make time for your passions, for play, for purpose, and for projects and people you care about.

Your Freelance Portfolio gives you the freedom to live the life you love—and to spread that love around—while fulfilling your professional and personal responsibility to make a living and do it well. It keeps you connected with your larger life plan. It enables you to change that plan when your life goals change. And it reminds you that all work is noble when you’re working for something you believe in: yourself.

MY FREELANCE PORTFOLIO

LEVEL 1: BLUE CHIPS

The core of your Freelance Portfolio. Like so-called blue-chip stocks, they’re your buy-and-hold investments: major clients (large or small in size) that provide regular income and work.

LEVEL 2: GROWTH INVESTMENTS

The growing edge of your business and the incubator of Blue Chips. Level 2s come from referrals, client testimonials, maintaining your network, and cultivating new contacts and prospects.

LEVEL 3: ONE-SHOTS AND LONG SHOTS

Opportunistic gigs that fill time or income gaps.

LEVEL 4: NEW VENTURES AND GROWTH

In Level 4, you’re building the services, products, and alliances that will produce income in the long-term future.