What’s your biggest challenge when it comes to doing work that matters?

A lot of people say money. As in, a lack of money.

A lack of money can certainly be an obstacle. But it can also be an excuse.

It’s awesome to have the funds we need to give us the time and other resources that will help us do work that matters. But if we say we can’t do anything meaningful because it’s not our full-time job, that’s fear talking.

Now, there are cases where money truly is a debilitating issue. I have friends and family members who just can’t seem to get ahead — at times they feel as if they’re drowning. Money problems can be extremely demotivating, crippling, and depressing.

However, right now I want to talk about those who see money as their biggest challenge to doing work that matters and yet have never stopped to consider if there are alternatives. Or perhaps you see the paycheck as a validation of the work you’re doing — you need the promise of income as a pat on the back that you’re doing something valuable.

But the truth is…

Money is a tool, not a validation

You with money may have an advantage over you without money, but it’s not a guarantee. At the end of the day, what money does is buy opportunity.

• Opportunity of time: if you had a million dollars in the bank to pay all your monthly living expenses and to pay someone else to handle all the menial tasks of your life, then you could spend all your time working on your craft. But even if you had all the time in the world, it doesn’t guarantee you’d choose to do meaningful work.

• Opportunity of collaboration and community: if you had a million dollars, you could hire a team to work with. But even with a hundred million, there’s no guarantee that you’d be able to hire an all-star staff of hard-working, kind, fun, brilliant, self-starters who all get along.

• Opportunity of networking: if you had a million dollars, people might invite you to their fancy dinners, and ask you to collaborate with them. But even if so, there’s no guarantee that the right people will notice you

• Opportunity of research and discovery: if you had a million dollars you could buy all the books you need to learn up on a subject, travel somewhere to a conference to meet new people and learn new things, and more.

• Opportunity to use better tools: if you had a million dollars you could buy the nicest camera, the fastest computer, the highest quality paint brushes. But even then, there’s no guarantee that the tools at your disposal would empower you do to work that matters.

If money is your biggest challenge to doing your best creative work, ask yourself what advantage or opportunity it is that you’re looking to money to solve. Once you figure that out, ask yourself if there’s a different solution to your challenge.

If you say you need money so you can have more time to do the work that matters to you, and yet you’re watching an hour of TV every day, then money’s not the first problem. How you’re spending your time is.

If you say you need money to afford the right tools, yet you go out to eat every day and have a monthly car payment, perhaps you should assess your spending and budgeting.

The real obstacles are fear and not being willing to sacrifice

I spent four years writing shawnblanc.net during evenings, weekends, and lunch breaks before I was able to quit my job and take the website full time. Jason Kottke had been writing online for 7 years before he quit his job to take kottke.org full-time. Myke Hurley spent four years podcasting before he was able to take his passion full-time. John Gruber wrote Daring Fireball on the side for 4 years before making it his full-time gig.

In short, it takes time — years, usually — before doing the work you love can get to a point where it is also the work that pays the bills. But sometimes, it never pays the bills.

Are you willing to show up every day for 4 years?

Talking to a friend about this just this morning, he said that he doesn’t think it’s about money at all — it’s about how much people are willing to sacrifice to do the work they love. People don’t want to give up all the things they need to give up, so instead they place the burden of action on having more money.

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In her book, The Crossroads of Should and Must, Elle Luna writes that there are four obstacles to doing our most important work: Money, Time, Space, and Vulnerability.

While money, time, and space are the reasons given most often for not choosing Must, there’s another fear that’s far scarier and spoon about much less.

Choosing Must means that you have to confront some very big fears. It will make you feel vulnerable.

Doing our best creative work day in and day out is difficult. As anyone who writes, draws, or takes pictures on a regular basis can tell you, thinking and creating something awesome every day can be hard and frightful.

I don’t want to minimize how helpful it can be to have a financial safety net in place, nor how frightening it can be when you’re barely scraping by. I’ve been in debt, I’ve lived paycheck to paycheck even though I didn’t have to, I’ve survived on less than minimum wage, and I’ve had enough money to take a year off if I wanted. In all those seasons, there were still challenges and fears that I had to press through in order to do work that mattered.

Elle Luna also writes: “It is here, standing at the crossroads of Should and Must, that we feel the enormous reality of our fears, and this is the moment when many of us decide against following our intuition, turning away from that place where nothing is guaranteed, nothing is known, and everything is possible.”

With all kindness and tenderness, let me challenge you: If it’s mostly about the money, then perhaps it’s not about doing your best creative work after all. If you see money as your biggest challenge, perhaps you’re not being honest with yourself.

This is what my home office workspace looked like in 2007:

(I still have that trashcan. And the weird blocks underneath the legs of the desk are there because I mis-measured by about 3/4 of an inch when I was shortening the height of the desk to something more comfortable.)

It was dorky, but it was also inspirational. Inspirational for what it stood for, really. That photo was taken around the same time as the beginning of my weekends-and-evenings freelancing career. I had just bought that refurbished Mac Pro and 23-inch Apple Cinema Display, and now I was ready for the big leagues. It felt great to have a new machine (doing print design on the 12-inch PowerBook was not very ideal), and a newly organized workspace with some semblance of organization and structure. You know the feeling.

A few years later, we ripped out the carpet to reveal the hardwood underneath. Painted the walls, got a new desk from IKEA, and bought a lamp.

That’s the desk where I launched my full-time gig writing shawnblanc.net.

A few years after that, we moved my office downstairs because the upstairs room was to become a nursery for our first son, Noah.

Here’s what my space looked like last year (2014):

Since that time things have de-cluttered a bit. Mostly thanks to the Retina iMac (which is still incredible by the way).

Here’s what my desk looks like today (2015):

As desks are wont to do, mine certainly gets cluttered and messy. But I try to keep it clean and not just let the mess get out of control. For me, inspiration and ideas and calm are more prevalent when the peripherals are dealt with.

My desk is where I spend so much of my time. It’s where I work and where I create. I write, design, pay bills, ignore emails, edit and share pictures with my family, and more… all from here. I’m here right now, in fact.

When I think about showing up every day and doing my best creative work, I think about this space. It has certainly changed and evolved over the past decade, but one thing it’s always had has been a surface to work on, a keyboard to type on, and an internet connection to publish through.

Your creative workspace may be different. But regardless of what or why you’ve got what you’ve got, here are a few things every good creative workspace needs:

• Ritual: As I wrote last week, by far and away, the best thing you can do for your creative workspace is to build some ritual / routine into it. When you combine the power of a consistent “where” along with a consistent “what and when”, then you’re basically putting your creative genius on autopilot.

• Fun: Having fun is an excellent way to do our best creative work. If there’s nothing playful, enjoyable, or fun about your workspace how can you hope to create anything inspirational or vibrant? All work and no play makes our creative work very dull indeed.

For me, I have fun built right into the very core of what I do: writing. My keyboard is as clicky as they come, and I love it. Secondly, I have a computer that I love to use: the Retina iMac which is a marvel. As someone who works with words all day long not only do I have my favorite way to type them with, I also have a jaw-dropping display to view them on.

• Inspiration Rich: Speaking of fun, a good workspace is inspirational. A few friends of mine who have some pretty great workspaces include: Sean McCabe’s office, which is filled with art prints; Cameron Moll’s space which is very open and organized, but yet also is clearly lived in; and Jeff Sheldon’s office studio, which, like Cameron’s is very organized but very lived in.

I have a bit of inspiration in my place. My bookcase is packed with hardbacks, paperbacks, magazines, Field Notes, Moleskins, and Baron Figs. On the walls are prints of photographs I’ve taken over the years. But looking at some of the aforementioned office spaces, I know there is much I could do to enhance the life, vibrancy, and overall inspiration of my own workspace.

• Distraction Poor: A good workspace empowers us to do our best creative work. Distractions are pretty much the opposite of inspiration and motivation. In addition to not letting myself check any stats or social media before I’ve put in my morning writing time, I also get rid of physical distractions in a couple of ways.

For one, I clean up my desk at the end of the day so that tomorrow when I come down to work, there’s nothing left undone that I need to tend to first. Secondly, I put on headphones. I work form home, but right upstairs are two toddler boys whose superpowers include turning into tornadoes.

• Efficiency: This is threefold. For one, it’s critical to have the right tools for the right job. You wouldn’t want a butter knife when you’re trying to cut down an oak tree. Secondly, get the best tools you can. I don’t mean get the best tools period, get what you can afford and what you can handle. Lastly, a good workspace is efficient in that it can accommodate what you use on a regular basis and that everything is easily accessible while not also being in the way.

• Multiple Spaces: This one’s a luxury, but it’s also so great. If you checked out the photos of Sean, Cameron, and/or Jeff’s offices you may have noticed that there were multiple “stations”. Their offices have more than one physical place to do work.

In my office there is my desk, but on the other half of the room is a couch and coffee table. And, even my desk converts between a sitting and standing desk. I have these different stations because not all creative work is created equal. I spend at least as much time writing as I do reading and researching. And that latter activity is better spent not in front of my computer.

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In her book, The Crossroads of Should and Must, Elle Luna lists Space (as in Workspace, not Outer Space), as one of the four obstacles that stand in the way of us doing our most important work — what she calls our “Must”.

Elle writes:

You need a physical space — private, safe, and just for you. When you are in this space, you are not available. I repeat, you are not available. This is your sacred space to be by and with yourself. We all need safe containers. How might you create a safe space that you can spend time in daily? How might you get creative with where it begins and ends? Find this place and make it your own.

The unsung hero of showing up every day and doing your best creative work is your workspace. You may think it’s your determination, zeal, and creative genius. And it probably is. But it’s also that you’ve somehow managed to carve out a spot where you can think and work without judgment, inhibition, or distraction.

Your space doesn’t have to be made with a desk or a computer. I read about one woman who made her workspace by using painter’s tape to section off part of her living room. She ran the tape across the ceiling, down the walls, and back over the floor.

I’ve had many productive days at coffee shops. Find a table where nobody will give you the stink eye if you’re there for too long, put on headphones if you like, and make your space with an Americano as your wingman.

Perhaps you’ve created your workspace intentionally, or perhaps unintentionally. But either way, if you find that you’ve been doing some of your best work lately, take a moment to thank your space.

However, if you’re struggling — if you don’t have a space — it’s time to make one.

Having fun is an excellent way to do our best creative work.

But as anyone who writes or draws or takes pictures for a living will tell you, thinking and creating something awesome every day can be excruciatingly painful. Doing our best creative work day in and day out is difficult. Creative work wears on your mind and your emotions instead of on your joints and muscles. Not to mention the sheer horror involved in the act of taking something you’ve created and putting it out there in public in the hopes of making a dollar so you can make something else and put it out there again.

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On Episode 5 of The Weekly Briefly, Patrick Rhone was my guest and we were sharing some bits of writing advice for people wanting to build a website audience. One of the foundational principals we both agreed on was the immeasurable importance of having fun, which is not as easy as it sounds. As I mentioned above, publishing your creative work to the internet for all the world to see is often a very not-fun thing to do.

Patrick said something that is an excellent guiding principal to help you keep your writing fun: write the internet that you want to read.

There is something freeing about creating for yourself. When we take hold of that baton and create for that second version of ourselves, it’s like having a permission slip to do awesome work. And what better way to have fun than to do awesome work? There’s an inverse truth here as well: most of our best work comes from the place of delight. When we are excited about a project, that creative momentum propels us to think outside the box and to dream new ideas as the project takes residence as the top idea in our mind.

Bill Watterson, the creator of Calvin and Hobbes, would agree. Here’s an excerpt from a speech he gave in 1990 at the Kenyon College commencement ceremony:

If I’ve learned one thing from being a cartoonist, it’s how important playing is to creativity and happiness. My job is essentially to come up with 365 ideas a year.
If you ever want to find out just how uninteresting you really are, get a job where the quality and frequency of your thoughts determine your livelihood. I’ve found that the only way I can keep writing every day, year after year, is to let my mind wander into new territories. To do that, I’ve had to cultivate a kind of mental playfulness.

And here’s James Altucher in a Facebook status update about how to write for a living:

The most important thing for me: writing without fear. Writing without judgment. Writing without anger. Making writing fun. Writing right now. Writing is about freedom and not money.

Now, as you probably know all too well, in practice it’s not that easy. But you and I are not alone in our fight to stay creative. We can (and we should!) set ourselves up for success. By identifying the things that suffocate fun and creativity, as well as knowing the things that encourage creativity, we can wage war against the former and cultivate the latter.

Let’s start with the bad news first.

Stiflers of creativity

Below, I’ve listed the things that will cut off our ability and/or desire to do our best creative work. These are things that will whisper in our ear that our idea is pathetic and our implementation of it even worse. They urge us to give up, to move on, to quit, and to pacify our minds. They tell us that we have nothing unique to offer, that we have no value, and that everything will come crashing down any minute, so why even bother.

• Isolation: Being alone from any community, any peer group, and anybody who you can bounce ideas off of, get feedback from, and just other general human contact that reminds you of the fact you’re a real human being.

• Ambiguity: Having unknown goals and trying to complete them in an undefined manner with a hazy schedule. Without clear goals, an action plan to accomplish them, and a schedule for when we are going to work, then we just meander around not actually doing anything.

• Fear & anxiety: This includes fear of failure, fear of rejection. It can paralyze us from even getting started on our ideas because we fear it will come to nothing in the end anyway. Or we fear that when we are finished, people will reject our work and reject us as the author behind it. The problem here is that it puts all the value on the end result only, and places no value at all in the journey of the creative process itself. There is nothing wrong with failure and rejection — we can learn so much from those things! And there is no shortcut for experience. We mustn’t be afraid of failing nor of being rejected, and we must place more value on the act of creating so we can find joy in the journey and develop a lifetime of experience in making things.

• Shame: Feeling inadequate as an artist at all, embarrassed about the work we’ve done, even embarrassed about the future work we haven’t even done yet. When we feel shame, we shy away from our big bold ideas and the result is a self-fulfilling prophecy and we make something completely devoid of life and opinion.

• Doubt: Doubting that we have the skills to make anything at all; doubting our value as a creative person.

• Comparison: There is a difference between learning and gleaning from others and comparing our work to theirs. Where there is comparison there is often envy as well. And this deadly pair will choke out any originality we have. Ray Bradbury, from his Martian Chronicles introduction, wrote: “I did what most writers do at their beginnings: emulated my elders, imitated my peers, thus turning away from any possibility of discovering truths beneath my skin and behind my eyes.”

• Disillusionment: This is “a feeling of disappointment resulting from the discovery that something is not as good as one believed it to be.” We can get disillusioned in a million ways, and often the result is a loss of vision for doing our creative work. I avoid disillusionment by steering clear of the things and the people that represent what I consider the “worst” things of my areas of interest and work.

When we live with these stiflers of creativity as a permanent ailment for too long, it can lead to burn out. The solution isn’t to quit our creative endeavors altogether, but rather to get rid of the ailment. I will say, however, that quitting (or taking a sabbatical) works sometimes because when you fully remove yourself from the situation you have a chance to deal with the ailment in a new environment.

Identify these enemies in your creative life and wage war against them. Give yourself permission to do what it takes to set yourself up to do the best creative work you can do. Quit Twitter. Move to Atlanta. Only write and publish after 9pm at night. Whatever.

Stimulators and proponents of creativity

These are the things we want to cultivate as much as possible. Build these into your life and guard them with tenacity. These are not replacements for talent, knowledge, and perseverance — rather they are the things that serve as both the seedbed and the greenhouse in which creativity grows and flourishes.

• Community: You need community to help cultivate your ideas, encourage you to keep working, and to speak truth to you about the things you’re afraid of. If you work from home, community can be tricky. Have a chat room where some of your close friends are available; get out and go to coffee shops or parks; work from a coworking space regularly; eat meals with friends; actively engage in non-work-related relationships.

• Clear goals: Having a defined goal can help us to focus on actually accomplishing our idea and making it happen. Looming, unanswered questions often lead to inaction and procrastination. Overcoming that is often as simple as defining an end goal. Of course, it’s worth noting that sometimes you just want to go out and take photographs and who cares what you shoot. Nothing wrong with that either, of course.

• Trust: You have to trust your skills, trust your gut, and trust your value as a contributor. You’re not an impostor. And the more you learn and the more experience you gain, the more your skills will grow. But if you wait until you’ve “arrived” to begin your journey, it’s a logical impossibility that you will ever actually arrive. You have to step out the front door and start walking.

• Experience: The more times we’ve gone down the same path, the more familiar with it we become. Experience breeds confidence. And confidence is the opposite of doubt. Thus, the more we do the work, the better we get at it. In part, we are getting better because that’s what happens when you practice. But also, we get better because the confidence which experience breeds helps us to loosen up, relax, and take new risks.

• Rest: A surprisingly critical part of maintaining a consistently creative lifestyle is stepping away from the creative work at hand in order to recharge. The mind is like a battery, however — it recharges by running. Don’t default to TV and video games as your forms of rest. Get plenty of sleep. Take walks or drives. If you work with your mind, try resting with your hands and build something out of wood or plant a garden. Read. Etc.

• Diligence: This includes spending our time wisely, having a routine, focus, and automation. Diligence isn’t a personality type, it’s a skill we learn. Some of us had a good work ethic instilled in us by our parents, some of us have had to cultivate it on our own later in life. It is silly to think a creative person should live without routine, discipline, or accountability. Sure, inspiration often comes to us when we least expect it, and so by all means, let us allow exceptions to our schedules. But sitting around being idle while we wait for inspiration is a good way to get nothing done. And worse, it is also a way to let the creative juices get stagnant.

Other factors and variables

There are some response-based factors that don’t make or break an artist in and of themselves, but, depending on what they are (and our response to them), they can empower or handicap us.

• Tools: Tools do not an artist make nor break; but the right tools can empower us to be more efficient and the wrong tools can slow us down.

• Constraint: Constraint often breeds creativity because it forces us to think outside of the box, but too much constraint can actually stifle a project’s full potential.

• Praise & criticism: The positive and negative feedback of people can be dangerous. If we take it to heart too much, it can easily lead to pride or depression. We should glean from the feedback we get, but not let it steer us in our goals and direction. One of the most dangerous questions a creative person can ask themselves is: “What if the critics are right?” If they’re right, you’ll already have known it. Let the council of your peers lead you, not the one-off praise or rejection of strangers.

• Success & failure: Similar to praise and criticism, success and failure can be dangerous. Our successes and failures should be things we learn from and use as stepping stones in our ever-continuing journey to make awesome things. Successes and failures should be celebrated and learned from, but don’t treat them as stopping points.

• Environment: A positive work environment can do wonders for your daily creative productivity. A distracting environment can stifle things. Do what you can to set up and maintain an awesome environment that fosters inspiration, creativity, focus, and fun.

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As Hemingway said: “Write drunk; edit sober.” Alcohol aside, the point is that creating without inhibition results in better work in the end. Have fun when making, and go back later to fix those typos and bunny trails.

But, that’s not to say fun is the premier goal that in the fight to stay creative. The goal — the hope — is that we can do our best creative work, day in and day out, for years and years.

What’s so great about having fun in our creative work is that it stands as a signal, telling us we are “in the zone”. When we’re having fun in our creative work it usually means we feel safe to dream big and to take new risks. Not to mention, when we’re having fun, it gives us a natural energy that helps us persevere and bring our ideas to life.

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P.S. This topic of staying creative has a significant presence in my book, Delight is in the Details. It’s such a critical discussion that I also made a video about it. You can watch the video here and buy the book here.