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Lessons learned being an “Indie” Designer

Over a year ago Chris (my cofounder) and I embarked upon the murky waters of the startup universe.

Lessons learned being an “Indie” Designer


Over a year ago Chris (my cofounder) and I embarked upon the murky waters of the startup universe. I "toed the line" between running Wiseacre Digital and building a product with ChoreMonster for several months, until things turned a corner (i.e., ChoreMonster got venture funding). I packed my bags and waved goodbye to nearly a decade of being a freelancer — or as I prefer to call it — indie designer. Recently an old graphic I created on Dribbble has been turned into a tshirt, and I thought "Maybe I could share some of the things I learned working for myself?", where I succeeded and where I failed. This is by no means comprehensive of all the things you need to know when starting your own graphic design business, but I believe covers a great deal of things you need to be prepared for before and while you do.

Don't Be Desperate

My introduction into the independent world of design (I loath the term freelance, but I don’t have time to get into that right now) was not voluntary. Panic was my suit, my state of being (as was faith, but mostly panic). I was unprepared and acted out of desperation. I wasn't a salesman. I wasn't a marketer. I wasn't known. I had no connections (and this was 2001, there was no social media, other than message boards). How could I make money for my family (afterall I had two young children to support and a wife who was a fulltime mom). I felt worthless. I asked (begged) everyone I knew if they or anyone needed help with design — anything in design: logos, print, web. That desperation made me devalue my worth. I traded my pride for pennies in a cup because I believed it was all I could do to survive. While I had a lot of small projects and a few contract opportunities, the amount of time and money I made effectively canceled the other out. My estimated hourly rate shrunk as I spent more time on projects (because I was not only doing the design, but the programming and development, the administrative work and the client management). It became a cycle, a boulder down a mountain I couldn't stop. It took me five years to learn how to stop it. To find my pride and worth.

Find Advocates

I stopped the avalanche with trust. My distrust of people and their intentions (or abilities) led me to do things I wasn't fit to do. I was overmatched and stressed, and in that stress made many poor decisions. I met a few people who restored my trust in humanity (or more to the point, lifted my fear), and through them I started to value my work and allowed them to become my advocate. Finding others with which to collaborate is one of the most important things you can do as an indie designer. You simply cannot succeed (or grow your business, because that's what it is, a business, it's not just design — design is only about 40% of what you do) without others. Know your weaknesses and find people to make it a strength.

Be In A Community

The only way to find advocates is to become involved in a community (outside your home — while it's true that kids are naturally creative, I don't think your clients appreciate farty-poopy humor in their communications; usually). I mistakenly thought that "getting out there" was frivolous. I worked and worked. Every moment of the day I was on the clock — if I wasn't making money I was wasting it. I was alone, at home all the time. I was an island and stranded. This not only stifled my work, it stifled my growth. While being billable is very important, so is being sane. Find a place to go where there are people. I know this sounds obvious, or easy, but it's not. Go with no agenda. Go with only the idea of finding like-minded friends. Commiserate. Drink. This will always yield a magical outcome. Call it serendipity. Call it providence. There is no science to finding your advocates — your eventual partners — but it doesn't happen without intentionality.

Set Strong Boundaries

Working at home makes sense (if you're an indie designer). Your overhead is low. You don't have rent. You don't have to spend on gas or parking or food or clothing (I literally did work in my pajamas). I consciously worked from home because I wanted to be around my kids. I was able to take timeouts — eat lunch with them, put them down for a nap, play pretend in the backyard. I wanted to actively be in their lives. Given the chance, I would choose to do this each time, even today. It was the right decision (for me). I loved my kids, and I wanted to be a decidedly purposeful father (and more available than my own father). I believed (and still believe) that fatherhood was more important than being a famous designer. But that decision also involved a lot of sacrifice (in more ways than I actually knew). There was no big money (not as much as someone who worked at an agency/studio). There was no advancement. There was no recognition (this was in the young days of the internet, when social media didn't exist — the "known" designers where those that spoke at AIGA events, that published articles in PRINT, Eye, Emigre, HOW Design, ID, et al). There was no time.

Working at home with kids is horrible. For the first few years I worked in a very small area — the width of a window  in our bedroom (the only other option was a desk/hutch area in our dining room in our very small house inhabited with non-school aged children always about). When we moved to our current house we made sure that it had a separate, quiet office for me. One would think that this is enough to shield you from the distractions of your own, lovely, angelic, perfect children — but one would be wrong. Since you're at home it is nearly impossible for one not to spill into the other. There will come a point, hypothetically, where your wife will have her hands full with one child deciding to use applesauce to paint the dog while the other child has forgotten how to use the potty and pooped on the wood floor, hypothetically, and it will be impossible for you not to help out (since you are there, after all), hypothetically. A few moments a week will turn into several moments a day and the "Daddy's working leave him alone" will turn into "Daddy's here, let's tell him about how we just farted".

You have to set solid, unflinching and sometimes cruel boundaries. Why? Because being pulled from work to home becomes a divide that takes time to cross. That time adds up, and that time becomes lost hours and lost money. When my office door was closed, no matter how much knocking, screaming, begging my kids did — I would not answer. I was at work (just as if I were not in the same house). When I left my office, whether to get a snack or go to the bathroom, I was still working. That doesn't mean I ignored my kids, but I couldn't engage them (which really means I was ignoring them, but I don't want to sound like a horrible person).

But these hard boundaries didn't just apply to my family, it also applied to clients. I told my clients that they could contact me at any time during the day, but any phone calls between 9am and 4pm would be sent to voicemail, wherein after 4pm I would call them back, otherwise they could send me an email. Random interruptions disrupt productivity. Controlling how those disruptions flow allows you to maintain your productivity.

Don't Be An Asshole

This sounds like simple and obvious advice, and it is. What it means is that you're working at the mercy of those that entrust their business communications in your hands. You both are risking something for the other. Your time is their time. Your creativity is their creativity. While you're an expert, that doesn't give you license to be an asshole. One can be frank and honest without being condescending and unprofessional. Don't lie and say that you're a "company" when it's just you. Believe me, being a "freelancer" will be a problem for many clients — the perception that you cannot manage their needs on your own might be legitimate, but unless you carry yourself professionally, establish consistent communication, clear boundaries and managing expectations, you will not conquer those perceptions. I was guilty of this starting out, I was so afraid of not gaining work, I worked under the guise of a studio. I misled. I lied. It got me work in the short term, but my efforts to keep the client happy led to putting in more time than my estimates and effectively lowering my hourly rate. Building a collaborative team is essential. While you might work alone, having a team of others skilled positions will eliminate (some) client doubt and land your larger clients with larger budgets. Lying to a potential client by saying you're a "company" will never go well, because you're starting a relationship on a lie.

Love It Or Leave It

If you're an indie designer, you must be one with the same mentality as someone who is running an agency (or any business for that matter). You're not merely a designer. If you hate accounting, if you hate client management, if you hate looking for and paying for health insurance, if you hate the inconsistency and the "feast and famine" cycle, if you hate programming and development, if you hate sales, and you have no one else to manage those things you hate, then find another job. Don't play with other people's money and trust because you're afraid. Love what you do or leave. Love doesn't mean bliss, but it does mean commitment and truth to the business you willingly entered.

For a long time I hated waking up. I was stressed and worried every moment of the day. I had no idea how I was going to survive from one month to the next. I created enormous amounts of debt because of it. I operated like a man with a gun to his head. I came to the point where I wanted to jump off a cliff, but instead I turned around and faced the stampede. I owned my problems. I owned my decisions. I found pride and self-respect. I found advocates. I ruthlessly pursued healthy boundaries. I stopped being an asshole. I became a businessman. All in all, don't make my mistakes. Find yourself and go.