Lessons on Creative Work

These are lessons I learned while building my indie business, consulting, and pursuing creative work-but you may find some universality in your pursuits. I'm writing them in the second tense, but they are written to me, about me. They may cut directly against your life situation. Take from them what you want to, and throw away the rest. I'll try to keep it away from well-trodden territory.

Some of these may feel obvious, some not, but I found many of them very hard to internalize. Don't expect that just by reading this post you'll have embodied the lessons, you may have to learn them yourself many times over. I know I do.

This is an on-going list that I will continue to update.

#W1: The impact of your work is neither equitable nor consistent. Decisions you make can have compounding effects and provide you with value for years to come, while toiling for months can lead to dead ends. Try to make good decisions early and when something is working, don't feel compelled to change it–you may just make it worse.

#W2: Inspiration and motivation comes in waves. Rather than trying to force yourself to be perpetually motivated, embrace it when it comes, and don't punish yourself when it's gone. If you are struggling to feel inspired, go pursue more life outside of the screen.

#W3: Goals are nice, but the joy felt achieving them is often short-lived and may not fulfill you. A consistent situation that aligns with your values does. Try to fall in love with the process. If you don't, you'll be chasing a feeling rather than a situation. Situations tend to last, feelings might not¹¹  A.J. Brown on winning the Super Bowl: 'I tried to feel how everyone made it seem to be a champion and unfortunately it was short lived.. two days to be exact...It's the journey that I love the most.'. Look for rolling success - meaning, a fulfilling situation that is on-going.

#W4: Be very intentional about what it is you hope to accomplish with your creative pursuit. Intentional doesn't mean you have to know all the possible results, but don't waste your time pursuing a project or business where you won't be happy with the idealized outcome. If you don't want to work 60 hours/week and manage 100 people, maybe don't raise venture capital and chase a billion dollar valuation.

#W5: It is incredibly hard to ship full projects. The more times you release your work into the world, the more you realize it never gets any easier²²  I don't think this holds for smaller projects, like a blog post or short creative piece. Those do get easier. Full projects like websites, apps, films, businesses, etc remain hard.. The last five or ten percent is almost always 50% of the effort. Keep pushing, don't be afraid to release something. Even if it "fails", you've learned far more than you would from most college courses. I have built fifteen or twenty projects: only one of them ever made a dime, but it was all worth it. Others have been very successful in different ways. Most no longer exist.

#W6: The best way to get over your fear of shipping is to stop holding yourself to an impossible standard. It's probably better than you think it is, and if it's not: you'll gain clarity on why for the next project. It can be hard to objectively analyze your own work until it's publicized.

#W7: Initial ideas don't exist fully formed, you have to work through them to see them out. This means ideas are almost worthless, and execution is everything. No one will solve a problem the way you do; and if they already solved your problem well, consider yourself lucky. You don't have to spend years toiling away: you just had your problem solved instantly. More ideas will come, trust your creativity. No need to hold onto them too tightly.

#W8: Working hard and consistently is the best way to improve your craft. This is how everyone you respect became great. It is almost never an accident and talent alone doesn't carry forever. It's easier to keep a habit going than it is to keep restarting it. Don't envy other's skill, just keep working and you will catch up. You never see the hours they put in.

#W9: If you're stuck on a problem, take a shower. Lay down and try to go to sleep. Context-switch if you have to. Those are the moments in which your active brain turns off and your subconscious starts to process. You can't brute-force every problem.

#W10: Discussing your ideas in excess before building them often releases the pent up energy you have to pursue them and may zap your motivation. The more you talk about something, the less likely it is you'll actually do it.

#W11: Life is more than just work. Far more. Make time for family and friends. Foster or join a community. It is incredibly important to being fulfilled, especially if you work alone.

#W12: Don't get stuck on individual ideas. The path to success is lined with failures, if you feel your first idea must be a success then you are holding yourself to a very idealized standard. Fail quickly and make more stuff. Your current idea is just one of many you will have. What's going to be better: your first project or your tenth? So don't get stuck on your first project forever.

#C1: Always put your own oxygen mask on first–meaning, ensuring you have your basic necessities³³  A good thread to unravel here is Maslow's Hierarchy of Needs (eating well, financial stability, mental well-being, etc.) will lead you to freer creativity than if you are constantly struggling. If you want to pursue art, there are ways to make it work–find your balance.

#C2: Find things that inspire you outside of your creative medium. If you are a software developer, analyze your favorite band. Or a chef. Or a film-maker. Figure out the things you like about their work and find ways to imbue them into your own. Realize that they are all their own business and try to understand how they make it function.

#C3: Trust and develop your taste, as it is your voice. Pay attention to what resonates and what doesn't. Be yourself. Taste and skill grow over time, don't get angsty that your skill is not yet commensurate with your taste. Just keep building and it'll eventually catch up. If you're young, realize that as you get older time gets stretchier and stretchier.

#C4: Creativity comes from enmeshing yourself with the world around you. Ideas don't come from within, but are generally captured from the outside. This is why parallel thinking is so common. This can be freeing, because the onus is no longer on you. As Bob Dylan stated: "The songs are there. They exist all by themselves just waiting for someone to write them down. I just put them down on paper. If I didn't do it, somebody else would."

#C5: Unravel threads in completely unrelated fields. They tend to come back in ways you can't anticipate. Invest in hobbies, learn how to make a new cuisine, discover the beauty of calligraphy⁴⁴  Steve Jobs on Calligraphy: [video]. Pursue the things that intrigue you and they will eventually influence your work. "You can't connect the dots looking forward, you can only connect them looking backwards."

#C6: Creativity is a muscle that you can grow and flex. It is not just innate ability. Approach problems from different angles, solve problems that are tertiary or unrelated. Get weird with it.

#C7: The more you hone your craft, the more creative you can be around the edges. This grounds your work and can give you a better launching pad to get creative without it devolving.

#B1: Do the dumb thing in business. Take a month off and build something completely unrelated. Give away your product for free because it's Wednesday and you love Wednesdays. It doesn't matter. Lean into the dumb thing and you will be surprised, and will likely come out ahead in the long run. Not everything is an efficiency game where you have to make the perfect decision. The Grateful Dead let everyone record and share their concerts for free – people thought they were idiots. It led them to being one of the biggest bands on the planet and billions of dollars in revenue.

#B2: Being your own boss is incredible, but it means you have to figure out what to do every day. Sometimes, having someone tell you what to do is wonderful. With autonomy comes responsibility.

#B3: Make something people need. If you don't want to feel like you're going uphill against your users, make something they can not live without. You can growth-hack a million different ways, but the only true path to sustainable growth is making something that people need. If you think people don't need spotify or that starbucks coffee, you are wrong.

#B4: Launch and validate quickly. If you can't build it in three months or less, find a way to validate it without building it. For B2B: if someone won't hand you a $100 bill today for a problem you promise to solve for them in the future, they don't really need what you're selling. For B2C: understand that it will often take years of growth before you reach profitability or saturation, and you'll have to be the one to grow it (marketing). Shipping is incredibly hard and yet it is only day 1.

#B5: Living in a capitalist society means we are trained by default to try and extract maximum value. You don't have to extract maximum value if you do not have shareholders to answer to. You can lose money if it makes you happy. Long tail gains are always better than short term gains because they compound. Pursuing maximum value is an easy way to squeeze your business and your happiness.

#B6: User-experience is king. Make sure yours is great. It's more important than design, or logos, or a dot-com domain. Less is more, if more means cutting corners. You can always add more later when you get the small bits correct. All businesses are user experience at their core.

#B7: User-experience is king, but all friction isn't bad. Friction adds depth and nuance. Friction gives your product character. Sometimes making things harder or more unique leads to more emotional bonding. Not everything needs to be hand-held. A perfectly friction-less experience is a boring experience⁵⁵  This is not the case if you are building tax software or a note-taking app. If your product is boring-be boring.. Think of the modern speakeasy – step into a non-descript phone booth and utter a barely "secret" code before you can enter – the friction makes the experience.

#B8: Minimum Viable Product (MVP) means MINIMUM and VIABLE. It's right there in the name. Do the minimum that is viable. Don't do too little otherwise it won't be viable. Most people skip past minimum and do way too much. It's a hard-learned lesson. Threading that needle is delicate, but you'll eventually start to see it.

#B9: Understand your network effects. Does your project only work with a critical mass of users (e.g. social media)? Can you find a way to self-sustain growth through word-of-mouth, so you don't have to market it as much? Are you willing to put the soft-work in after you launch to feed that growth? Don't be afraid to build on top of existing platforms if you are small, as you get a network for free.

#B10: If you do build on top of an existing platform, make sure they have a history of being profoundly open. The platform could decide they don't want people building on top of them anymore, and you will be in for a rude awakening. Understand that the risk here is your business can be effectively terminated at any point out of your control, and come to terms with that outcome as soon as possible. They don't owe you anything: you got their network for free⁶⁶  Apollo was shut down by Reddit. Tweetbot was curbed by Twitter. At the end of the day, they appear to have been wild financial successes for their creators. You run the risk. I chose to build on top of Valve and I understand it could end any day.. Know this tradeoff, but again, don't consider it a dealbreaker - it can be an incredible cheat-code.

#B11: Marketing is just communication. Speak honestly and from the heart. If you are solving a real problem then your words will resonate, if you are not then go back to the drawing board. You can't beat the niche knowledge that comes from having experienced a problem yourself. Marketing can only do so much if people don't genuinely need what you're selling.

#B12: The best marketing is word-of-mouth. If your user has a great experience, you'll not only have a customer, but an advertisement.

#B13: Charge money for your product, if people really need it they will pay for it. You'll be surprised. This might sound simple, but it's hard to get over that mental hurdle because we have impossibly high standards for ourselves, and undersell our personal worth. Since we do live in a capitalist society, having people pay for your product is perhaps the most honest form of democratic validation. The money itself isn't the important part, creating a sustainable situation is.

#B14: Take a holistic approach to product development. A/B testing and KPIs can help you squeeze a few extra percentage points of revenue or efficiency, but at smaller scales they can end up being more of a distraction. It's much more important to make sure the holistic user experience is great, than to worry about if the button should be blue or red. Stop worrying about metrics and just focus on nailing the core experience.

#B15: Talk to your customers, but understand that they are just one data point who don't have the full picture. They often don't even really know what they want. Don't give them more credence than that anecdotal evidence actually represents.

#B16: Strive to create a situation in which both you and the customer have aligned incentives. Meaning, don't sell their data or exploit them. They pay you for a product and you provide them with a consistent experience. End of transaction – you both win.

#B17: Figure out what it really is that you want from your business. Most people think it's just 'money', but when you dig in deeper what they often really desire is: autonomy, independence, fulfillment, contribution, and security. If it is just money, that's okay, but really sit down and ask why yourself you're doing this. Adjust your direction for the things that really matter to you. Don't live out society's desires just because it's what you perceive success means to others. You define success.

#F1: Don't bill hourly as a freelancer unless your rates are astronomical. You are playing against yourself and creative work can not be measured in hours. How do you bill for problem solving while you're in the shower? Bill healthy day or weekly rates. The consistent income you get will far surpass the few times you overwork yourself for a small payout, and you are no longer incentivized to put in empty hours. Get your work done early and use that time for yourself. As we know from #W1: work effort/hours are not equitable. Your billing should be a function of experience, communication, and deliverables: not granular time. Companies like fixed-rate-contracts because it helps them budget, there are no surprises.

#F2: Discuss in advance what the expected deliverables are, even if on a week-by-week basis. If you are efficient, you can deliver them on time without spending 40 hours per week. Companies won't care if you work less than 40 hours in my experience. As long as you deliver high quality work on time, they won't even think about you – they have full-time employees to worry about. If they're ever upset with your output, have an honest discussion and offer them a refund or ensure you work harder next week to catch up. You'll find the balance quickly. Don't promise that you'll work X number of hours, promise that you'll deliver your work on time with high quality and back it up.

#F3: Try to raise your rates a little bit at each new company, they may say no, but they generally will be open to negotiation. The goal is not to maximize your income, but to afford yourself as much flexibility as you can.

#F4: This is somewhat counter-intuitive, but the higher you charge, the more respect you will get and the more likely you will get paid on time. Once you reach a certain threshold, all the hostility you receive as a freelancer seems to melt away. It's the cheap companies who expect the world and treat you poorly.

#F5: The most important skill you can have as a freelancer is a healthy balance of communication. They are hiring you for your expertise and autonomy, be judicious when choosing to ask questions and just answer them yourself if you can. The less you go to them, the more they'll appreciate you. Take stuff off their plates, don't put stuff on them. If the questions you have can be deferred and are non-blocking, wait until the end of the week and ask them all at once instead of individually.

#F6: You can freelance and pursue your personal work on the side. The idea that you need to have full focus on your business or pursuit is incorrect, it's much better to have income and even a little seed money than feel strained. With constrained time you'll be less likely to waste it anyway, and with constrained income or well-being, you'll struggle to complete your personal work.

#F7: The best gigs are working for medium-sized companies on internal tools or projects. There are very few deadlines, little bureaucracy, and you'll be a relatively small line-item on the budget. Plus the company will love you because your co-workers will use your work directly. They may keep you on contract for a while because the cost of not having you when something goes wrong is much higher.

#F8: The fewer meetings you have, the fewer hours you have to work. Meetings always take a fixed amount of time, creative work does not. Since you are not billing hourly, you have no need to worry about "hours". Set your boundaries early.

#F9: Don't be afraid to be honest about exactly what you want (hours, pay structure, in-office, etc.). Just ask – though you may have to first build trust. They won't hold you to the same standards as a full-time employee.

Build up to these. You can't show up as a freelancer on Day 1 and expect to take advantage of all of these ideas. But you can sprinkle them in as you gain more confidence and skill. You may have to bill hourly when you're first starting out, but you will know when you're ready to make the switch.

#S1: Try to model your data structures correctly early. Always start with the data structure before writing code. They're much harder to change in the future and will invariably make your life more difficult. Really think deeply about how things may change and grow in the future, so keep them flexible.

#S2: Just ship it. Once in a while, though, rewrite an entire feature immediately after you've gotten it working. It'll teach you how to better do that in the future so you don't make the same mistakes. You'll begin to see yourself getting it right the first time.

#S3: Make best friends with the devops team. Tell them "thank you" often. They are always underappreciated and inevitably will be the only ones who can unblock you when you need to deploy something.

#S4: The best technology is the one that solves your problems effectively and that you know well. End-users will never see your code or systems, they only see its shadow.

#S5: Full rewrites take far longer than you could ever anticipate. If you plan to pursue that, try and force yourself to add zero new features or design-changes beyond architecture improvements.

#Co1: If you can afford it, pay for indie software and art. It's the best way to ensure that it survives. Your wallet is far more powerful than you may realize. If something costs the same as a coffee or beer and it brings you value, you'd be foolish not to support it.

#Co2: What you choose to surround yourself with, what you choose to consume is like giving someone else sudo⁷⁷  For the non-software engineers, this means giving them admin access access to your brain. Everything you give attention to constructs your own personal reality. Be judicious - within reason.

If you have any questions or want further clarification, or you just want to tell me how wrong I am: drop me email me below.