The Art of Freelancing: Know Thyself

Quantifying Freelance Work & Optimising for Happiness

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“But I have no leisure for them at all; and the reason, my friend, is this: I am not yet able, as the Delphic inscription has it, to know myself; so it seems to me ridiculous, when I do not yet know that, to investigate irrelevant things.”

Socrates in Plato’s Phaedrus

“Know thyself” is a Greek aphorism which pops up throughout historical philosophy. Some of the most practical, interesting philosophers of the past two millennia have written about the two-word rule, including Plato, Benjamin Franklin and Emerson. This short gem of a phrase is particularly applicable to freelancers as we are naturally independent and must rely on our own wits each and every day.

I would argue that most freelancers know themselves more than most employees. It’s inherent in what we do. Freelancing puts you in touch with your customers, your accountant and your ROI, directly; so in a business sense at least, we know ourselves more than most. So why this post? Because we can use this Greek aphorism to become better freelancers. Way better.
Let me explain.

Freelance Work Direction - Self Leadership through knowing

Freelancing Starts Simply, But Where is it Heading?

We all start out as simple freelancers. We dig in. We’re “developers” or “designers” but many clients later, many projects later; we find niches we enjoy more than others. We find things that we’re good at. We specialise. To my mind that’s important, to specialise is to commit oneself to something, to focus, to make smaller circles.

So here’s how I see it for us. We’re freelancers, we like to build, to be creative and we like to deliver. Perhaps we like the production of the thing because we’re actually throwing lots of ideas up in the air to see what sticks. What works, where and how? My theory is that we are natural optimisers, or at least, we are naturally seeking something which we haven’t found elsewhere. We seek it through the medium of project or piece work.

To start with, we might be looking for a way to feed the kids, or pay the rent, but once that’s out of the way the natural progression is to connect the dots forwards. Where is this all leading? What do I want to end up doing? Trust me, it’s all leading somewhere. If we dig down and analyse our progressions, fumbled attempts and our excitement to do the work, we’ll find out which direction we’re headed. We’ll find out what we really want.

Once you’re comfortably making ends meet as a freelancer, pay attention to yourself.

Know yourself freelancer: Quantify what you do, optimise your value proposition and then rinse and repeat all the way to happy, high level freelancing.

So we start off knowing a little something about ourselves, we approach freelancing with vigour, and then we learn more. This is the start of the journey, but if we are to properly aim for happiness and success we must be unambiguous about what we want. We must build into everything we do an awareness of ourselves and the efficacy of our actions. By quantifying our work we can find patterns, from these patterns we can discern what works and what makes us happy. The trick is to identify and then do more of these things.

4 Ways Freelancers should apply “Know Thyself”

  • Quantify Time Spent
  • Analyse Workflow (stress per pound etc.)
  • Optimise Workday
  • Optimise Clients & Pipeline

… or in other words:

  • Observe & Record (thyself)
  • Analyse & Optimise (thyself)
  • Internalise (thy) Optimisations
  • Externalise (thy) Optimisations

We must build a loop of self-analysis which guides our freelance work, and that all starts with quantifying…

Quantifying your freelance work

Quantifying Our Freelance Work

Not unrelated to this topic is the Quantified Self movement. QS is booming. Their bi-line reads “self knowledge through numbers,” and that’s our aim here too. There’s rarely been a more exciting time to be a lone worker with movements like QS taking off, but for now let’s focus on the work.

How quantified is your work? Do you track your time? Track your down-time? Your accountancy hours, or how many bids you put in on work, to get what return? Do you track stress per pound (or dollar?) These are good things to record.

If you work in a large company, they might give you half-year reviews. You may get a boss checking up on your performance once a week. This is the company quantifying your work and their relationship with you. As a freelancer, (as we keep saying) you run the show, so this becomes your job. At the start, this is a chore. Tracking time in itself can be a strain until you get it, but there’s huge value in it. Self review is essential.

When we don’t track our time we guesstimate, we lose money with false-accuracy or to distractions. When we do track our time we force ourselves to become consciously aware of the value of concentration, the cost of distractions and our overall personal attentiveness.

To start quantifying our freelance work, first we record two things religiously:

  • What time is being spent
  • What that time is invested in

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The recording in of itself will illuminate your habits. The first month I started recording my time I realised I was spending equal amounts of time playing computer games as I was eating lunch, and that some jobs paid off for me far more than I thought they did. Equally I spotted a client who was causing me many hours of communication but gave me poor quality work. I axed him. Thank you Pareto and Tim Ferriss.

Analysing Yourself as a Freelancer

Once you’ve got the tracking down, and you’ve come to terms with your vagrant habits, you can learn lots of things from your own data:

  • Stress per £ or $?
  • How long are you spending looking for work?
  • Are you billing clients enough? Fairly?
  • Are you delivering on time? Including a margin of safety?
  • Projecting forwards, what does a year’s salary look like?
  • Would you be happy working these hours for a year? For that money?
  • Any positive/negative patterns? (ducking out of work early on a Friday?)

… and this is just the beginning of creaming understanding out of quantifying work. There are fantastic things we can learn about ourselves from watching how we do what we do. By being aware of the good and the bad we can guide our future decisions. We can realise what we love to do, and move more and more towards running a business that makes us want to jump out of bed in the morning.

Analyse for happiness and meaning

Bonus Points (Pro level Quantifying):

  • Record mood per work session
  • Record sleep hours, family/social time and find correlations to work
  • Factor in the each projects’ skill development value to you
  • Factor in the resell/reuse value (adding to your code or graphic libraries)
  • Factor in the promotional / portfolio value to you
  • Use all this learning to diversify your pipeline and stabilise your business

Block a day each month to do this analysis. I call mine my “Sustainability Day.” Check over all your time logs, projects completed/secured. Remember the most stressful times and your favourite parts. Sum it all up in a relaxed way and then try and work out ways to optimise your workday to promote the good and cut the bad. Read on for ways to optimise your workday.

Optimising Your Freelance Workday

You’ve timed yourself doing everything for weeks, you’ve noticed you don’t work well on Thursdays, and one client has an insanely high Stress-per-pound rate. He’s causing you two freak-outs a week and isn’t even paying that well. So what then? How do freelancer’s best act on their quantifying? I’ll share ways in which I’ve optimised my freelancing below, but feel free to make them your own. As epic freelancers we often love imagining systems, and you run your freelancing shop, so what you say, goes. Please do share any ways you’ve optimised your day in the comments below.

Limit your freelancing hours

Weekly Limits

The first realisation I had when I analysed my freelancing time logs was that I was spending 60-80 hours a week sitting at a computer doing something which resembles work. This struck me as a big chunk of time. I’ve run companies for as long as I can remember, so I am not afraid of a bit of hard work, but I’m also totally certain that I didn’t need to be at a screen for that long. To remedy this I dug through my hours and eliminated some tasks which weren’t helping all that much, cut down my email time and decided to set some limits.

By internalising a semi limit of 40-60 hour weeks I was able to achieve most of the work I was doing before, but in far less time. Checking mid-week how many hours I’d done gave me a short-term guide as to how many hours I should max out at over the rest of the week. I didn’t set a hard number, but rather I set a practice of awareness of my numbers. Pretty soon I settled into a shorter week, was less burnt out generally, and still billed just as much. Work often takes up the time allocated to it. Allocate less, and manage it.

40 hours can be a lot

If you’re being highly creative 40 hours a week, that in itself will drain you quickly. Companies shout about 40 hour weeks because it works for the majority, but as freelancers we work for the minority, ourselves. Even 40 hour weeks aren’t always productive. Find your happy level of hours and train yourself to respect it, for your own benefit!


From quantifying my time at a computer I learned a lot about myself. I was reminded how distracting email was and I learned that computer games can much more time than you think they do. I saw in vivid detail how fractured my days had become. 37 minutes coding, 11 minutes responding to a client email, an hour coding, lunch. Coding, email, break, phone, email coding.

Like a fragmented hard drive my day (and brain) had become messy and painful. I narrowed down the culprits to a mixture of concentration-breaking-notifications and coffee. I quit both. If you get to the end of a year and look back and see 500 hours of email, or worse, 1,000 hours of gaming, are you going to feel accomplished? Will either add to your profits or skillset? There’s nothing wrong with relaxing with a game, but beware of distractions!

I set myself a new challenge: to deal with email within 20 minutes a day, max. And to do it in one sitting. This has been written about many times, and it worked for me. If you don’t believe me, try it. Clients may occasionally have imperative deadlines, but for that there’s Skype or a phone. What I did notice is the clients that were relaxed, calm and sure of themselves were fine with a daily email routine, the needy clients flipped out. You know what to do with them.

*For more email optimisation fun see for gmail

By clearing blocks of work time, and focusing on doing one thing well, without distraction, I did much better work. What’s more I enjoyed it, and I haven’t burnt out since.

Freelancers Should Meditate

Good habits

The next part of my workday I noticed inefficiencies in is probably the most common amongst all freelancers. It’s the reason I started EverClients.

Bidding. I noticed that with the ebb and flow of projects I would often not bid on new work or spend anytime marketing for weeks, only to be left with an empty week without work. I’d then spend the whole week hustling, bidding on new jobs or hunting down repeat work from clients. A huge takeaway from this was that I hated it, it took hours, and often I’d take cheaper/weaker fill work to “just get something in the door.”

Then I developed a good habit by internalising my values. I was a good developer, I constantly had good reviews from clients. I didn’t need to chase any work for the sake of filling the time. I decided that I should remind myself of the fact. I should seek out new work consistently in smaller nuggets of time and overall worry less about the whole process.

By building a daily bidding/marketing habit I was able to keep a more regular stream of better quality work which meant when I did have down time it was relaxed and rejuvenating.

Lastly, and perhaps a sidewinder habit to mention here, I began meditating. I started practising back to breath meditation each morning. This daily practice is akin to recording your time, only for your mind. It teaches you to have awareness over your own (often distracting) thoughts and to maintain a healthy calm. It only takes 10 minutes.

These are just a few of the ways I’ve internalised improvements to my working day by keeping track of it. Next up are the ways I’ve found to externalise the same improvements, so that we prime ourselves and others around us for our freelancing to be the progression of our craft.

Optimising the Finding of Freelance Work

Not all work is equal. Find only the good stuff

Once you understand how you are spending your time, and what you want to spend your time on, you’re on track to progressing towards happier, healthier freelancing. The last step in the cycle is to externalise these facts. We do this by optimising the way in which we find work and deal with work. We show the world the way which we want to run our freelancing business.

Stress Per Pound

Once I’d built a good habit out of bidding on new work each day I became starkly aware that there was a particular strain of client that stressed me out.

They’d want fifty changes and hold payment over my head until they manipulated a response. They’d want you to be reliable but be wholly unreliable themselves. From this irritation I coined the phrase: Stress per Pound. These clients often paid okay rates. They might even pay a little more than other clients, but for every £1 they paid me I’d get 10x the stress, and this wasn’t good stress.

Soon after realising this I went about working out ways I could minimise my exposure to bad stress per pound clients and maximise my good clients.

Promote your best clients

Profile and Champion Great Clients

In dealing with the screamers we often forget the quiet, polite, reliable clients. We must remember the great clients, and not let the screamers steal our attention away, because it’s these clients which are worth their weight in gold to us. An extension of knowing ourselves is to know the types of people whom we want to spend time working with.

To be happy freelancers we must:
Curate Our Clientele

I achieved this by profiling my best clients, working out some commonalities, like what their aspirations were, or where they hung out online (also useful for marketing.) I identified that I most enjoyed working for entrepreneurial clients who were developing novel web apps, typically working within the lean methodology. They were successful middle-age people (some of which continue to be clients and friends to this day) and hired from one of two sites.

By being aware of my ideal customer and over-delivering to the clients which matched, I was able to build stronger, ongoing relationships. I received more referrals and more easily found other great clients which helped my freelancing no end.

Profile and Filter Out Bad Clients

It’s not all good though

There will always be challenging clients. I decided to profile my bad clients as well, and came up with a set of identifiers and ‘trapdoors’ to deal with them. Bad clients can cause all kinds of disturbances in our freelancer flow, from adverse stress, to work-droughts and financial losses. By maintaining an image of my ideal worst customer I was able to compare each new potential client to the two models I created. Best customer vs Worst customer.

Over time I’ve got better and better at deciding which end of the spectrum a potential customer will end up being, but there are always surprise cases.

A few months after I started doing this analysis I also realised that the quality with which I make this judgement is totally dependent on 1.) how tired I am, 2.) the state of cash-flow. I’ve learned through this that honing your intuition is something you have to just keep working at.

Unambiguous Rules

As well as testing clients to weed out the trouble ones we can also build hard rules into freelancing which provides another level of defence. We decide what we will do, and what we won’t. We stick to it.

“ The minimum commission I take on is four hours per day. Weekends & evenings are triple rate ”

Nobody wants to bill someone for twenty minutes worth of work. If you can fix something for a client, what’s the value to them? Likely it’s at least four hours of your time, otherwise (at least in my experience) the emails and the correspondence means the job wasn’t even worth it (though I know there’s value in serving quality clients without needing return, it’s a fine line sometimes.)

For me setting a minimum commission time meant that I could block out half days or days, it stopped me being tempted by smaller jobs. It was a rule for both potential clients and myself, and each time I stuck to to the rule it reinforced the fact within myself. I only want to work on substantial jobs from invested clients.

Promote The Good

Tailor your marketing to finding great clients

Along with my daily bidding habit mentioned above, I built a habit of maintaining my marketing. Instead of taking filler work I invested in my pipeline (see improving your pipeline.) I kept my value proposition in keeping with the things I’d learned about myself recently and with the direction I wanted to work in. If I noticed I enjoyed a specific project I’d look for ways to market that.

This was me externalising all of the lessons I’d learned from quantifying and analysing myself. I tweaked my funnel to ensure I got more work that I enjoyed.

By promoting a few good projects above some arguably better work I got fast into developing prototype apps and WordPress plugins. Before that I’d developed all over the place, but I soon found that I was great at rapid application development (RAD) and that for me, that was the most profitable, fun, and least stress-per-pound work.

I tailored my marketing appropriately. I tweaked my profiles on job sites and changed the clients I was searching for. From there I got more prototype work and I earned and learned even more. This practice has helped my freelancing tremendously.

Observe, analyse and apply. Create a loop, where each time around we get better. It’s the iterative, evolutionary, freelancer approach!

As freelancers we can optimise for happiness, rather than for money, or we can optimise for both. We have that control.

EverClients for Freelancers

The Freelancing Loop of Self

In the end we’re building loops of self awareness

In reflection, since I’ve taken on the aphorism of “Know Thyself,” I’ve been naturally optimising; training myself into running in a loop. I’ve been observing, recording, analysing, internalising and then externalising my self as I work freelance, again and again.

This may seem very existential but in fact for me it’s been particularly practical. It’s let me practice the skills I’ve wanted to, it’s paid me to learn more about myself and invest in what I’ve learned.

I see freelancing as a great way of learning more about yourself. It’s a low-barrier-to-entry way of throwing up lots of ideas and seeing what sticks. To the observant freelancer, working for many clients on many jobs gives many opportunities for enhancement. We have chosen a career path which can give nuggetised challenges, digestible and achievable steps towards competency, and ultimately happiness through knowing ourselves.


About The Author

Woody Hayday - The Art of FreelanceThis is the second in a series of blog posts about the art of freelancing. If you like what you’ve read you can follow me @woodyhayday or sign up for blog updates below.

Did I miss anything? Please do Comment, or tweet me out. See you next week for the next post: The State of Freelance

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