What have you learned after one year in business?

Advice from The Sherwins for August 2017

Happy Anniversary to You


Hi Sherwins,

I’m thinking about taking the leap from my current job and launching my own design business with a friend. Since you started your company last year, what have you learned that could help me out? I’d appreciate it!

O in Colorado


Hello O,

Good question! On the one-year anniversary of Ask The Sherwins, we popped a bottle of sparkling cider, put some poblano mac ‘n’ cheese in the oven to cook, and jotted down the 37.5 things we’ve learned from our first year running our own consulting and training business. Some of them, we probably knew before we started, but let’s just say… there’s knowing and knowing.

Here they are, in no particular order.

1. Do what you said you were going to do, when you said you were going to do it.

2. Don’t schedule back-to-back meetings.

3. You don’t need to work at the same time or keep the same hours or even work on the same days as your partners. Just communicate that to each other so you can plan meetings and stuff.

4. Debrief after each meeting with your business partner, even if you both attended.

5. Naps are awesome.

6. Schedule time for self-care into your workday, even if it’s just watching an episode of RuPaul’s Drag Race.

7. Have working hours. Don’t “work whenever you feel like it” or “catch up on email while watching RuPaul’s Drag Race”.

8. Bill what you work.

9. Coffee dates and meetups and phone calls should be considered business development, even if business development is a department of one. Track that time. If this is hard for you, consider using time-tracking software.

10. Create clear expectations regarding how you want to work together, even if you’ve known each other for decades. Regularly check in with each other. Time passes. Things change. Including you.

11. Get off your phone.

12. Keep a notebook by your bed. Before bed, write down your list of things to do tomorrow on the left side of the page. On the right side of the page, write down the questions you’re trying to answer right now. This practice is amazing for insomniacs and worriers alike.

13. Have a formal, scheduled payday. Celebrate it.

14. Cultivate at least two hobbies or activities that don't overlap with your everyday work.

15. Some clients will have a contract that says they don’t want you to tell anyone that you’ve worked for them. Ask them if you can change that. They might say yes.

16. As a matter of fact, no one’s going to change anything unless you ask. So ask for the things that you want. This is true for everything in life.

17. Worry less about networking.

18. Worry more about having coffee with lots of people that you enjoy talking to, and that you think you can learn from—even if it’s not related to work.

18.5 This is for Bay Area people: “Let’s have coffee sometime” translates to “Hah! I’m never going to talk to you again”. So if someone actually does schedule coffee with you, do not mess it up.

19. Don’t ask for advice from people you don’t respect. Life is too short.

20. Don’t confuse respecting someone for liking someone. Our lives, our work, our discipline, heck, even our country, all rely on being able to disagree with some semblance of civility.

21. Don’t rush through conversations with other people.

22. Get a good lawyer. Bonus points if they’re fun like ours.

23. Don’t complain that lawyers are expensive. Lawyers are expensive, which is why everyone who can make your life miserable already has one. Factor legal fees into your operating overhead and your estimates for contracts.

24. There’s more to life than design thinking.

25. Make sure every estimate has an expiration date. Otherwise, you won’t be able to keep track of your availability for prospective clients.

26. Oh yeah, keep track of your availability. On a calendar.

27. Keep up on your health insurance. And your taxes.

28. Don’t forget the rest of the everyday office stuff either. Incorporation documents, business license, seller’s permit, business insurance, all the domain names you own, etc. etc. Schedule it into your workday.

29. The emphasis in your home office is on home. Do the dishes. And the laundry.

30. You’re going to worry about money. Everyone does. Anyone who says they aren’t is lying.

31. Follow up. If you haven’t heard from someone and you should have, don’t wait around. They might have just escaped after being kidnapped by space unicorns, and you’d be the last person to know.

32. Don’t follow any of that “Meet one new person a week/fail seventeen times by lunch/puke in 300 countries before you die” stuff. It’s life, not a to-do list.

33. Take a moment every so often to teach each other something new. (Texting someone the link to an article is not teaching.)

34. Have a social media strategy, and be a little bit stricter with your image than you’re comfortable with.

35. There’s a fantastic intersection of stuff you want to do, stuff you’re good at, stuff the world needs, and stuff you can get paid for. (Google search: Ikigai.) Find that, figure out how to say it in a sentence or two, and then tell that to others.

36. Did we mention that naps are awesome? They are.

37. Do good work that you are proud of, even if at the end of it all, the client hates it and never wants to work with you again. You’re the one who has to look at yourself in the mirror every morning. No work is worth doing without dignity.

We could say more—and we did, in this book—but really, if you’ve got #1 and #37 down, you’ll do just fine.

The Sherwins


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The fine print: This advice will be around only for the month of August 2017. We keep getting questions from readers about this, and it's 100% true—each column is only online for a month.

Send questions to questions (at) askthesherwins (daht) com. All questions become the property of Ask the Sherwins, LLC and may be edited. Our advice shouldn't be construed as a replacement for the appropriate legal or professional counsel.