10 Invaluable Lessons Freelancers Can Learn from “Rework”

by Tom Ewer 10 Minutes

ReworkIn my opinion, the best thing about freelancing is the fact that we are in control of our destiny.

There’s no working our asses off in the vain hope of getting a raise. Hard work begets results. If you apply yourself to your business in an effective manner, you are likely to experience a positive outcome. There could be worse ways to make a living, right?

The simple fact is that there are always ways in which we can seek to improve and remodel our businesses. It could be anything from making more money, to working more efficiently, to dealing with better clients, to dealing with our existing clients more effectively, and any other number of things. With that in mind, in this post I want to give you ten actionable lessons from one of the best business books I have ever read that you can take away and use to improve your business right now.

What is Rework?

Ignore this book at your peril ~ Seth Godin

For those of you who don’t know, Rework is a book for business owners and entrepreneurs. However, it is unlikely to be like any business book you have read before.

Written by the founders of 37signals, it is essentially a collection of eighty-six short but highly actionable articles relating to startup and online businesses. Contained within is a number of wonderful lessons that can be adapted for our purposes as freelancers. And that is exactly what I am going to focus on in this post. Enjoy!

1. Forget About Formal Education

I have never let my schooling interfere with my education ~ Mark Twain

Many freelancers are not formally trained in whatever it is they get paid to do. Take me for example — I nearly failed English at school and have no writing or journalistic qualifications, and yet I make a good living as a freelance writer.

My point is this: you shouldn’t let concerns over a lack of qualifications or experience guide your goals. In fact, qualifications are far less important than you might think — consider for example the following statistic quoted within Rework:

Ninety percent of CEOs currently heading the top five hundred American companies did not receive undergraduate degrees from Ivy League colleges.

If they don’t need to be the (arbitrarily denoted) “best of the best,” why do you? Let your dreams guide your goals, not your preconceptions about qualifications and experience.

2. Planning is Guessing

Plans let the past drive the future.

I am a big fan of planning and goal setting, but I always plan with the following key principle in mind: your plan is only as effective as your willingness to remain flexible within an ever-changing environment. As the authors of Rework say, long term plans are essentially nothing more than “guesses [that are] inconsistent with innovation.”

If you are still adhering to a plan you dreamt up weeks or months ago, stop to ask yourself if that plan is still the best course of action. The likelihood is that you need to make (at the very least) some minor changes.

You have the most information when you’re doing something, not before you’ve done it.

Despite the reality of the above situation, plans are almost always written before you’ve even started down a particular path — i.e. when you do not have all the relevant information available.

I believe in planning, but more importantly, I believe in flexible planning. Have an idea of where you’re going, but make sure that idea doesn’t prevent you from changing direction and innovating when circumstances allow.

3. Workaholism

Working more doesn’t mean you care more or get more done. It just means you work more.

Has there ever been a time when you’ve felt wildly overworked? I’m pretty sure everyone will answer in the affirmative to that question. Now let me ask you this: since you are your own boss, why do you choose to work yourself like a slavedriver?

While you could probably give me any number of reasons to validate your workaholism, the simple fact is that overworking is not necessary. There is always a better way — a more efficient way — to get things done. You just need to figure out what that way is and apply it to your business.

I grew up with a father who was obsessed with his work. He dedicated more to his business than he would now say was healthy. I am determined to avoid the same mistake he made — I am passionate about leading a balanced life that involves work and play in equal measures. I am sure you feel the same, and yet so many of us still overwork ourselves.

Our culture celebrates the idea of the workaholic. We hear about people burning the midnight oil. The pull all-nighters and sleep at the office. It’s considered a badge of honour to kill yourself over a project. No amount of work is too much.

How many times have you come across someone who acts as if their ridiculously long working hours are something to be proud of? Can you actually recognize times when you have acted in that way yourself? It’s utterly absurd when you stop to consider it — why should working too hard be something you’re proud of? Wouldn’t building a successful business while working reasonable hours be more impressive?

You may say it’s all very well and good to say that one should work less, but how do you actually go about doing it? Well, I certainly don’t have all the answers, but I think Rework offers some quite compelling statements for you to consider carefully:

  • Workaholics wind up creating more problems than they solve.
  • [Overworking] isn’t sustainable over time. When the burnout crash comes — and it will — it’ll hit that much harder.
  • [Workaholics] try to fix problems by throwing sheer hours at them. They try to make up for intellectual laziness with brute force.
  • No one makes sharp decisions when tired.
  • Workaholics aren’t heroes…The real hero is already home because she figured out a faster way to get things done.

I like that last one especially. Give it some thought.

4. Draw a Line in the Sand

Great businesses have a point of view, not just a product or service.

Let me ask you one simple question: what is it about your business that sets you apart? Why should prospective clients choose you over the huge number of comparable businesses within your industry?

Until you have a genuinely compelling answer to that question, I don’t believe that your business is fully developed (in its current guise). Finding the answer to that question should be your number one priority for two reasons:

  1. It will make your business far more attractive to your ideal client
  2. It will make working so much more enjoyable

If you understand why it is you do what you do, your passion for doing that thing will be tangible in your work. For instance, I don’t write just write for Bidsketch so I can pay my bills. I write for Bidsketch because I have a passion for helping other freelancers like me. If just one reader tells me that I’ve helped them in some way through writing this post, I will feel rewarded in a way that no amount of money can emulate.

So what are your working for?

5. Embrace Constraints

Constraints are advantages in disguise.

People often bemoan constraints as killers of growth. “I can’t achieve x because of y” is an easy enough complaint to make, rather than facing the reality: constraints don’t prevent growth, a lack of innovation does.

The problem with a lack of constraints is that there is nothing to guide you. If the world is truly your oyster then where on earth do you start? On the other hand, if you are constrained by a lack of options then at least you know in which areas you need to concentrate.

From a freelancer’s perspective, consider a business model in which you offer a straightforward writing service compared to a full content marketing solution. One can naturally lead into another as a freelancing business develops but you wouldn’t want to try a full solution from the beginning unless you had past experience. In reality, the “constraints” of working only as a writer forces you to become an excellent writer, which will benefit your business no end now and in the future.

As it is said in Rework, “See how far you can get with what you have.”

6. Start at the Epicenter

The stuff you have to do is where you should begin.

Prioritizing is a bitch. It can seem that you spend as much time figuring out what to do as you do actually doing it. If you relate to that situation then always remember to start at the epicenter. Start with the single most important thing that drives your freelancing business.

Rework uses the analogy of a hot dog stall: worry about the hot dog; not the condiments, the cart, the name or the decoration. Without the hot dog itself, you don’t have a business.

To translate this into freelancing terms, consider the work of a graphic designer. What one thing can’t you live without in business terms? Your clients. If you have no clients then you have no business. So work on attracting new clients and retaining old ones. That is your epicenter. That is the work that is most important to you. It always gets first dibs on your attention.

7. Ignore the Details Early On

Nail the basics first and worry about the specifics later.

I am one for procrastination. I’d often rather think and talk about what I’m going to do then actually take action.

I’m sure we’re all guilty of this misdemeanour. Acting in such a way can be borne out of any number of motivations, but one of the greatest is fear. It’s easy to plan and get excited about offering a new service or redesigning your portfolio website, but actually releasing it to the world is something else altogether. We get caught up in the minutiae and sweat the small stuff.

But in reality, a lot of this worry is for nought and only serves as a brake on your business’ growth. Many of the minor details you sweat over are going to make very little difference to the end result. By actually making a start and putting your rough plan into action, you’re likely to find that what you thought were the critical details are actually replaced by the truly important matters. Perhaps the scope of your service needs to be adjusted, or the way in which your portfolio site needs to showcase your work should be presented in an entirely different way .

So don’t spend too long worrying about what may or may not be good for your business. Take action, observe the outcome, then decide how to proceed accordingly.

8. Reasons to Quit

It’s easy to put your head down and just work on what you think needs to be done. It’s a lot harder to pull your head up and ask why.

No one likes giving up. It can be relieving to do so but it’s rarely a good feeling. After all, we live in a culture that directly associates giving up with failure. If you stop trying to do something, you have failed in your endeavor.

That may be the case, but I’d rather fail than carry on regardless. Surely applying yourself to something that will eventually fail is far more of a failure than recognizing the futility of your efforts and calling it a day ahead of time?

If you ever feel like you are going down the wrong path or that the work you are doing is not necessarily in your business’ best interests, take a moment to ask yourself the following questions:

  • What is the motivation behind what you are doing?
  • Who benefits from what you are doing?
  • What problem are you solving?
  • Is what you are doing useful?
  • Are you adding value?
  • Is there an easier way?
  • What could you be doing instead?
  • Is it worth the time/cost/stress?

These are extraordinarily powerful questions that can be applied to everything from your bookkeeping system to the clients that you choose to work with. Ask them regularly and answer them honestly — I would go so far as to suggest that you print them out and place them somewhere prominent in your working environment.

9. Say No By Default

You rarely regret saying no. But you often wind up regretting saying yes.

I don’t know about you, but one of the biggest problems I have as a freelancer is saying no to prospective clients.

I can’t help myself — regardless of how much work I have on, if a tasty new lead gets in touch with an interesting offer, I’ll invariably say yes. I am wired to say yes by default, and I need to turn this around for the sake of my sanity and the growth of my business. That may seem counterintuitive, but accepting new clients mindlessly does not necessarily lead to long term growth.

In Rework the authors talk about making sure that “the product [that you are developing] stays right for you.” For freelancers, the issue is far more intrinsic — we are talking about making sure that your business stays right for you. We’re talking about making informed and rational decisions about who you choose to work with and why. Saying “yes” to a new client does not necessarily mean that your business is growing because true business growth is in my opinion represented by it developing into something that resembles your vision. More money in the short term does not necessarily equal growth.

So get into the habit of saying no by default. Starting with no and challenging yourself as to why you’re saying no makes you think far more clearly about the effect of each business decision that you make. On the other hand, saying yes to everything can quickly lead to a business that in no way resembles your vision.

10. Don’t Write It Down

The requests that really matter are the ones you’ll hear over and over.

Do you ever wonder where your business is going? Do you ever wonder what you can possibly do to drive growth? For most of us, the answer is lying right under our noses.

On the assumption that you have an existing client base, it is your clients that influence your growth more than any other factor. Consider this — unless you are going to completely pivot on your existing business model, any growth is going to be driven by client retention and development. Therefore, the future of your business lies in your ability to meet your clients’ developing needs.

Don’t make a major change to your business based upon some abstract notion, or something you read, or something you hear. Don’t change the way you work because one client requests it. Instead, gain a better understanding of the general trends of wants and desires that emerge from your clients. Don’t force this issue — just ask yourself what it is that your clients want the most and how you can help them in achieving it.

So many businesses try to manufacture growth by creating something that was never asked for. While that certainly can result in great success, the biggest wins are often screaming out for your attention, if only you would listen. So ask yourself — what do your clients want that you do not already offer them, and how can you cater to those desires?

Scratching the Surface

There you have it folks — ten lessons for freelancers that I took from Rework. If you enjoyed these then I strongly urge you to grab a copy of the book and get stuck into the rest of the chapters. While not everything relates directly to the world of freelancing, you will be amazed at how much of it resonates with your way of thinking.

We live in a brave new online world in which our limits are so often self-imposed — by thinking more innovatively and always looking to challenge ourselves, I believe that we are all capable of building highly successful businesses out of literally nothing.

I welcome any comments and questions that you may have below!

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by Tom Ewer
Tom Ewer and the WordCandy team have clocked some serious mileage as freelancers, agency employees and even agency owners over the years, and they love sharing their combined expertise here on the Bidsketch blog.