On this date ten years ago, I reflected on the first decade of my career as a designer, a professional milestone not unlike reaching a scenic overlook on a steep mountain climb or a mile marker on a rocky long-distance trek. As I looked back over the years and wrote each lesson, I conjured up all my successes and failures, the people who shaped my work and my thinking, the projects that pushed both my skill and my patience to their limits, and all the little everyday moments that had much more influence than I realized. In that short exercise of writing a retrospective blog post, it was like I had stopped to catch my breath and survey my travels so far — but also to take stock of the important things I had gained and, of course, to brace myself for the next leg of the journey.

Now at the end of the second decade, I really feel the passage of time, its psychological and experiential weight (not to mention the physical effects), but strangely, the timespans themselves feel much shorter than they actually are: 2009 seems like yesterday, and 1999 only last week. A lot has happened in these past ten years, in life and in design, and my transition to being self-employed in 2012 has brought with it new challenges but also opened new doors. Every single one of those original lessons has held true, some more than others. Today, I have twice as many to add: 

1. Set clear priorities for yourself. If you don’t manage your own time and attention, someone or something else will.
2. Suspend judgement. Let ideas flow before narrowing them down, especially in groups.
3. Beware of premature confidence and settling for incomplete information. You really don’t know until you know. (this is my personal mantra now)
4. Understand what matters to people so you can find common ground. 
5. Communicate intentionally. Have the right conversations in the right way; don’t rely on quick and lazy channels when a phone call or face-to-face meeting is what you really need. 
6. Always anticipate needs. Don’t wait for someone to ask you for something. Plan ahead for potential problems and proactively ask what more can be done.
7. Don’t be afraid to break from convention — champion possibilities. You don’t necessarily have to deliver on a client’s exact orders or submit passively to “the way we do things here” when there’s another and possibly better way. 
8. Take care with what you share. On social media and in casual conversations, speaking too freely or openly, or making your opinions too widely known can create more trouble than it’s worth. 
9. Be honest about the value you provide. Acknowledge how you can and can’t help a client, and be forthright about what might actually be wasteful or unnecessary.
10. Humanize your work. Talk like a real human being, not a robot. Read what people are feeling or expressing, not just what they are saying. And always try to represent people in drawings as human figures, not as boxes or words alone.
11. The burden of clarity is on you, not them. Don’t blame others for not “getting it,” no matter how obvious you think something is. Your job is to keep finding other ways until the light bulb goes off.
12. Be flexible, but within reason. Casual exploitation of your time and effort by a client is not cool, no matter how much you’re getting paid and no matter how much you don’t want to piss them off. Your value isn’t measured in dollars alone but your dignity as a professional who should be treated with as much respect as they demand of you.
13. Stay focused on your goals, and what it takes to get there. In meetings, in projects, and in life, be clear on what needs to happen, plan for success, and keep everyone on the same page. More coaching and encouragement, less policing and whip-cracking.
14. Disconnect like you mean it. Your personal time is valuable, so protect it: don’t even dare to peek at e-mail when you’re on vacation, because your mind will only be preoccupied with the work you’re not doing.
15. Streamline administrative stuff as much as possible. For small business owners who often wear lots of hats, there are lots of tasks to juggle: new business development, project delivery, project management, and everyday internal operations. Know where you need to spend your time and devote your attention, and what you can “set and forget” or automate.
16. Learn to say no without shutting the door. Requests and new projects pop up all the time, so make sure you know what you can realistically manage and tactfully set aside or redirect demands on your time with sensitivity to the person coming to you for help.
17. Take advantage of design history and design literature. There is a wealth of knowledge from generations past and from more recent thinkers that has relevance to many of today’s challenges. Don’t just accept someone else’s pre-digested take on a book or written work online — read it for yourself. If it’s not online, go find it in a library.
18. Build better relationships. Design is a people-driven business. How you interact with clients, co-workers, and others along the way matters more than you may realize. Simple gestures like sending a thank you card or offering guidance to a designer just starting out can make a big difference.
19. Know when to zoom in and zoom out. Some people prefer details and tactical planning, while others like the thousand-foot view and strategic thinking. Helping both kinds of people see the same picture together is absolutely essential to get everyone to solve a problem together.
20. Be grateful and show gratitude generously.

The real secret behind all of these little nuggets of wisdom is that the longer you keep at it, the more diligently you practice your craft and pursue the good in all you do, the more these insights will reveal themselves to you naturally, in the mistakes you make, in the problems you solve, and in the exciting and terrifying new frontiers that open up before you. And speaking of exciting and terrifying, with my peculiar sense of time, 2029 will be here before I know it.