Pygmy Nuthatch

Succeed Outrageously as an Independent Creator

  • The Pros and Cons of Anchor Clients

    The concept of the “anchor client” in important in freelancing. It’s a company that has you on contract for an indefinite period of time and typically supplies a fairly steady workload that doesn’t fluctuate much. Whether you charge by the hour, the week, or some other unit of measurement, you can expect that they’ll be there for you on a regular, ongoing basis.

    Sometimes freelancers get their start because their former employer continues to utilize their services on a contract basis. This can be a great way to launch into a new freelance career—however, there are some real dangers to be aware of (see the cons section below!) that have the potential to derail your business before it has the chance to really get off the ground.

    In an ideal world, you’d have two or three anchor clients and be raking in the dough—but things rarely work out that way! Over the years, I’ve usually had only one anchor client at a time and in leaner times haven’t had any. I believe ultimately the pros of having an anchor client outweigh the cons, but these are still issues you should be familiar with. Let’s dive right in.

    Pros of Anchor Clients

    They provide “jobby job” style cash flow. There’s great comfort in being able to project out several weeks or months and knowing what to expect in your level of income. Smaller client projects will come and go, but with this base of financial stability, it makes it much easier to plan for the future and possibly take on some risks (such as buying new equipment, moving into a new office, bringing on additional personnel, etc.).

    They supply a steady stream of work. After a while of juggling a large number of small projects, it can get quite tiring. The ability to block out a significant portion of the day to work on a single project for your anchor client can really help you get into a zen state of flow and maximize your sense of productivity.

    They give you the freedom to try out different side projects. With the extra mental capacity that comes from knowing you don’t need to hustle and drum up new contracts constantly just to keep the lights on, it frees you up to spend some extra time on side projects, continuing education, and other creative pursuits.

    Cons of Anchor Clients

    They might drop your contract suddenly, plunging you into financial chaos. You can attempt to come up with ways to mitigate this contractually, but in my experience you generally won’t see it coming and are suddenly left scrambling for new work. Whether the company has run into their own cash flow constraints and you’re the collateral damage, or they’ve changed directions strategically, it’s always frustrating when the rug is suddenly pulled out from under you.

    They can allow you to become complacent. If you have one anchor client that comprises more than 75% of your income, you’re essentially just an employee who happens to pay for your own benefits and other ancillary expenses. This is not a great way to build a business. In my opinion, you shouldn’t have any client that supplies more than 50% of your income. Diversification is what keeps the train rolling along and headed in the right direction, no matter what a single client may do unexpectedly. In addition, having a solid anchor client over time can lead to laziness in your sales pipeline. If you’ve just been working away on a big project for a long time and aren’t finding new leads and bringing in new business, that’s a major red flag.

    They might not pay what you feel you’re worth. As someone who charges by the hour, I’ve generally found that I make less money per hour working for anchor clients. Perhaps it’s because they negotiated for a lower rate—nothing wrong with that, since you’ll avoid spending so much time and cost bringing on smaller projects regularly. Or perhaps you’ve raised your rates once or twice since your anchor client first contracted with you and they’re still on the old rate (and possibly not likely to budge). If this is the case, you have a decision to make. Do you just let them get away with paying you less, causing you to lose in potential opportunity costs? Do you try to ratchet down your level of engagement with them as you bring on new, higher-paying clients? Do you simply ask them for more money to do the same work you’ve been doing? I’ve seen a lot of freelancers (including myself!) wrestle with this issue frequently.


    Overall, I believe freelance businesses are healthier when they have one or two anchor clients in the mix. As long as you’re aware of the potential pitfalls, avoid sales complacency, and strive to reach the level of income you’re worth, anchor clients will enable you to build a stable and successful freelance business for years to come.

  • 5 Reasons Why You Should Become a Free Agent

    For the the majority of my career, I’ve been an independent worker. It’s easy to take the lifestyle for granted after so much time being my own boss, but every now and then it’s good to take a step back and realize that—despite all the challenges that come with it—working as a free agent is a cherished privilege.

    If you’re thinking about making the leap, or you’ve already gone independent but second-guessing if this is really the lifestyle for you, here are five reasons why I think being a free agent—whether as a freelancer or a content creator—is undeniably fabulous.

    Reason #5: You can pick your own job title.

    I crave variety in my work. If I have to accomplish the same flavor of tasks every single day, I grow thoroughly bored. As a free agent, I’m able to seek out projects, technologies, and industries that interest me and help me stay motivated. I’ve designed websites for book publishers and written biographies of wedding DJs. I’ve engineered marketplaces for wine suppliers and customized enterprise XML editors. I’ve gotten paid as a graphics designer, a UX specialist, a software developer, a writer, a video editor, and (crossing my fingers) I hope to get paid to write a soundtrack some day!

    Reason #4: You can seek out people who do great work.

    When you’re part of a company with a corporate structure outside of your control, you work with the people you work with. That’s it. If you enjoy hanging out with them and admire their output, good for you! But if you don’t…well, your options are limited. When you’re an independent worker, you have the opportunity to assemble a team around different projects or initiatives and find people you love to work with. (Assuming they’re also free agents and are available!)

    Reason #3: You can bid farewell to that 9-5 desk job and see the world!

    As a free agent, you have full control over where (and when) you work. Sure, there may be certain expectations that you’ll be available at specific times for certain tasks, depending on the needs of your clients. But generally you’ll have a degree of freedom that’s difficult to find in the world of salaried positions. You’ll have a lot more leeway to travel, to work from home or a café or a cowork space or a library, or maybe even work onsite for different clients which can be a lot of fun too.

    Reason #2: You can let loose your inner entrepreneur.

    The relationship between employers and side projects can be a tricky one. Depending on the type of company you work for and the nature of your side project, you may discover that your employer is bothered by your focused attention away from their needs, or worse, they’ll want to claim your intellectual property as their own. No such hassle when you’re your own boss. You make up the rules! If you want to spend a few days now and then working on your own projects, or cram some effort into early mornings or nights or weekends, or alternate between weeks of client work and weeks of personal work (I know of a freelancer who did this and eventually switched to full-time work on their own software development)—it’s totally up to you.

    Reason #1: You can choose your own schedule.

    Which brings us to the top reason why you should become a free agent: time. Time is the most valuable asset you possess. It’s so valuable precisely because it’s so limited. You have a finite lifespan, and there’s no way you can add more time or buy extra time (short of debatable methods of buying your way into a healthier lifestyle which might increase your lifespan). Because time is so precious, your top priority as a worker and as a human is to be mindful of how you’re spending it. There’s nothing worse than finding yourself in a position where your control over your schedule is compromised.

    That’s why being a free agent is so incredible. You have full control over your work schedule. You decide what you’re going to do and when you’re going to do it. (Well, it is possible to arrange things with demanding clients such that you are a slave to their every whim. But I strongly recommend you avoid such projects like the plague!)

    If you want to get up at 6am and work until 3pm, go for it. If you want to roll out of bed at 10am and sit down at your desk at noon, who’s going to argue? If you want to take a long break in the middle of the day to enjoy some sunshine outdoors and make up for it at night, that’s totally your prerogative. If you want to charge more for your services so you can afford a 4-day workweek instead of 5, that’s well within your wheelhouse.

    At this point in my career, the freedom I have over when, where, and how I do my work is more important to me than anything else in business. I’m probably “unemployable” now, simply because I can’t imagine having as much flexibility working for a single company. I know of a lot of other free agents who feel exactly the same way. That’s why they’re free agents!

    So there you have it: 5 reasons why you should become a free agent. Can you think of a 6th? I’d love to hear about it!

  • Who Knew? The Future of Journalism is Transactional

    For years, we’ve had the notion drummed into our heads by internet nerds and pundits “in the know” that pay walls will fail and the very idea of charging for online content is absurd because nobody spends money on content—especially those pesky millennials who expect to get everything for free.

    Well it’s time to call it like it is: those pundits were wrong, very wrong. Pay walls and other types of paid content products work. Consumers have gotten trained to pay for online subscriptions to a wide array of products and services across a whole range of industries. Platforms like Patreon and Kickstarter have successfully allowed content creators to monetize their work. And now an increasing number of media businesses have reached the point—not a moment too soon in my opinion—where they are shifting their focus away from squeezing every last drop of ad revenue out of mass traffic and instead toward asking their audiences to pay directly for quality content.

    This is a far better state of affairs. I’m tired of being the product (the user) getting sold to the real customer (the advertiser). The biggest lie in the history of the internet is that content (and software in general) is free. It’s not. If you use a free service or read content for free, you are simply the product being sold to the real customers for real money—in other words, advertisers. And this ad-driven internet economy has had devistating effects on users’ security, privacy, and website performance—not to mention the rise of fake news and other “viral” phenomenons attempting to game the system.

    2017 was the year where this became a tipping point. Ad blocking technology went mainstream. Major computer companies (Apple primarily) centered their marketing around protecting the security and privacy of users. The scourge of fake news brought a reckoning to social media platforms. And sci-fi shows in the popular culture such as Black Mirror introduced us to the stark reality of how out-of-control social sharing and personal data tracking are paving the way to a dreadful dystopian future.

    Trevor Kaufman, CEO of paywall tech and customer intelligence firm Piano, has witnessed first hand this dramatic newsroom shift away from chasing social media and search traffic toward developing real transactional relationships with readers directly:

    “Every year, there are new costs that get added to the adtech economy that media companies rely on. First came viewability, then came ad blocking, then it was ad fraud. Clearly, the concentration of the duopoly has also been a factor. And just in the last year, we had very significant moves like what Apple did with Safari and third-party cookies. The Facebook feed changes are very significant. And so is General Data Protection Regulation in Europe.

    So what we see is a return to first-party data being vital and a return to thinking about readers as customers. They’re no longer cattle who are being monetized en masse, but rather people who we’re trying to appeal to and influence their behavior. That, again, has always been the business of media and marketing. I think it’s great to have a return to that.”

    Even more surprising (to some, not to me) is the fact that those darn millennials are not only showing a willingness to buy into this new reader-focused media landscape, they’re more willing to pay than their generational predecessors:

    “There’s also this crazy myth that millennials won’t pay for things, but the reality is that it’s boomers who won’t pay. Millennials are used to an à la carte world and are much more willing to pay for stuff. Overall, there’s a great rebalancing that’s happening right now.”

    In other words, the future of quality journalism and related media is transactional—audiences paying for access to content. That doesn’t necessarily mean we’re at the point now where everything is rosy. My personal belief is that the web needs a pervasive micropayments layer where people can easily share a percentage of a monthly money pool with content creators as they browse around normally. But in lieu of that, subscriptions to individual media sources or packaged media bundles seems to be the trend.

    However content gets monetized, I’m thrilled that this is the direction the media industry is heading. It’s high time we tipped the balance of power away from the Googles and Facebooks of the world and back into the hands of individual readers.

  • Vlogging about Portland, the Free Agent Lifestyle, and More

    Video has always been a deeply fascinating medium of communication for me, but my attempts to master it over the years have been haphazard at best.

    Last year I tried vlogging a bit on another YouTube channel centered around my electronic music making, but the concept never really solidified—and then I ended up doing the digital nomad thing and eventually moved to a different state, and that threw all my plans out the window.

    But I’m vlogging once again with renewed enthusiasm; this time under the auspices of Pygmy Nuthatch. Like so many vloggers, the pioneering work of Casey Neistat has had a big influence on me, but I’m also approaching this style from the standpoint of a musician, so a big part of the process is playing around with timing and emotional mood.

    I also love seeing travel videos from other parts of the world, and as I’m now living in Portland, Oregon, I want to capture the heart and soul of this beautiful area and share that with others.

    I’ve put out two episodes so far. For more to come, subscribe to my YouTube channel. Enjoy!


  • Emotional Health: Don't Ignore the Warning Signs

    As free agents, we have so many challenges to contend with on a regular basis: growing a client base or viewership, technological hurdles, cash flow, legal battles, industry disruption, rapidly changing trends, globalization, the rise of AI (no joke!)…the list goes on.

    However, the biggest challenge I believe is not something that’s outside of ourselves but is intrinsic to our very nature, and that is maintaining proper emotional health. The capacity to embrace an authentically positive attitude, along with the ability to resist reacting negatively to the bad stuff that comes up in life, is not only something that’s possible to cultivate but feels like a superpower when it kicks into high gear.

    The primary way I’ve developed this ability is through mindfulness exercises and spiritual development. But before you jump into how to solve a problem like ill emotional health, you need to know how to spot the warning signs. Here are a few I’ve come across:

    Glass Half-Empty World

    Some people are naturally optimistic. Other people are naturally pessimistic. I suspect most people generally shift back and forth depending on circumstance. I’m not here to tell you what your personality should be like—however, what should concern you is if you know you are normally an optimistic person but you find yourself in an increasingly pessimistic state of mind.

    Does the phone ring and you instinctively seize up wondering if it’s bad news? Are you avoiding certain difficult tasks or conversations because you just can’t imagine it going well? Do you wake up in the morning and wonder what’s going to go wrong today? These are all signals that your typical personality is being hijacked by abnormal mental patterns.

    It’s a Mad, Mad, Mad, Mad World

    Anger is a valid emotion that we rarely feel equipped to deal with in a healthy, productive way. Anger is how we react when we feel liked we’re under attack or wronged in some way. The question to ask yourself is, do you feel angry only when you are legitimately being violated in some major sense, or are you repeatedly getting angry over trivial matters?

    This issue was what finally convinced me I was struggling with depression in 2014. I was growing concerned and a bit baffled why things that seemed objectively like not a huge deal would set me off. The last straw was when I got unjustifiably mad at my wife and drove off to my office in a terrible huff, and then I quickly realized I was on a path to ruining our relationship. It was a clear sign I needed to reevaluate my emotional health.

    Scary, Real Scary World

    You’re going along, doing your thing, minding your own business, and suddenly you feel it coming on: the dreaded panic attack. Your heart starts racing, you feel a knot in your stomach, the walls start closing in…and the crazy thing is you can’t come up with a logical reason why you’re feeling this way.

    The long-term effects of chronic stress are finally starting to come to light via the medical community, and it’s not pretty. If you’re used to working in conditions that are typically stressful, it’s only a matter of time before your emotional as well as physical health is severely impacted. Mood swings, anxiety, fatigue, and symptoms similar to impairment from alcohol or drugs will start to invade your every day. If it gets really bad, you may even experience abnormal symptoms in the organs and systems of your body.

    I’m thankful my stress reactions never got too severe, but I was definitely struggling in this area (which certainly didn’t help matters as I tried to get out from under my cloud of depression).

    So What Do You Do Now?

    If you are dealing with any or all of these issues, I strongly recommend taking a course of action. If you do nothing and expect things to change, that is a dangerous road. Here are some of your options:

    • Read the literature. By far the biggest help for me personally was reading Mindsight and practicing the exercises therein. Mindfulness is a powerful tool to help stimulate our brains to develop new neural pathways and grow the capacity to avoid negative mental patterns.
    • Change your habits. If you do what you’ve always done, you’ll get what you’ve always got. While that might be poor English, it’s sound advice. I’ve written about the importance of switching up your routine and optimizing your work environment (here, here, here, and here).
    • See a trained professional. While I didn’t see a counselor specifically for my depression, my wife and I went to a couples therapist who specializes in the Gottman method (highly recommended, by the way), and indirectly that helped a lot in understanding my emotional states and how those might affect others in relational contexts.
    • Tell loved ones and friends what you’re going through. Sometimes all you need to do is just tell someone how you feel! Keeping your fears and concerns bottled up inside is a sure path to greater strain later on. If you don’t feel like you have enough people around you who you’re “safe” with and can share openly, that might be a contributing factor to depression all on its own. Even the most lone wolf person needs genuine connection with other humans.

    Emotional health is just as important as physical health, and making your health a top priority is key to achieving outrageous success in life and especially as a free agent. When your performance on the job is directly tied to your income or appeal as a creator, as it is with so many of us, the most important thing you can invest in is yourself.