The Reckless Optimists

The Pre-Work: Annie Kawasaki

Oct 20, 2026 · @Jessi

Start Here.

Annie, I'm so excited to dig into this with you. These questions are here to help me get to know you and your work a little more deeply before our offsite.

Some of them are practical and some are more personal. I've found both are helpful as we start building what's next for you, whatever shape that ends up taking.

Please don't overthink it. Write your answers out in a way that feels natural to you, with enough detail that I can follow your thinking. I'll read through everything and come to our offsite with lots more questions, so we'll go deeper together in the room. If you can send it to me the day before we meet, that would be perfect.

If a question feels hard to answer, write what you can and we'll explore it together.

Where You've Landed

It's been about two months since you walked out of HOKA. Before we look forward, let's notice where you are.

1.What's different? In your body, your mornings, your patience, your sleep. What's come back that you didn't realize was gone?

2.What do you miss, and what don't you miss at all? Both lists matter.

3.When someone asks “so what do you do now?”, what do you say? Write down exactly how you've been answering, and how it feels coming out of your mouth.

Who You Are Without the Badge

For twenty years, your title and the brands on your resume have done a lot of the introducing for you. I'd love to hear how you see yourself when they're not in the picture.

4.If you couldn't mention a title, a brand, or a shoe, how would you describe what you're great at?

5.When did you feel most like yourself at work? Pick a moment or two. What were you doing, who was in the room, and what did it feel like?

6.Tell me about something you're proud of that never showed up on a performance review. The quiet win. The person you helped. The thing nobody saw but you.

7.You told me service is one of your core values. What does serving someone well actually look like when you're the one doing it?

8.Send me your resume and LinkedIn, just as they are. No need to update or polish anything. I'd just like to see how you've been describing yourself.

Resume

LinkedIn URL

Anything you want me to know about them (optional)

The Practical Magic

Now let's talk about the work itself. Some of these questions may feel like they overlap a little, and that's okay. Different angles tend to bring up different stories.

9.What do people pull you into that isn't your job? At work, with friends, anywhere. What's the thing people say “ask Annie” about?

10.What's easy for you that you watch smart people struggle with? The storytelling around a product, the question nobody else thinks to ask, a brand voice that holds at every touchpoint, finding order in chaos. Use those as a start, but tell me what's actually true.

11.What work have you LOVED? The projects, seasons, and moments where you lost track of time. Go back as far as you want.

12.What work drains you, even when you're great at it? The tasks you never want on your plate again. This list matters just as much as the one above.

13.What makes you righteously indignant when it's done badly? I've found that what frustrates us often points toward what we know best.

14.Three wins you're proud of. Anywhere across Nike, Cole Haan, HOKA, or beyond. For each one: what was broken or at stake, what you did that someone else in your seat wouldn't have, and what changed because of you. Numbers are great if you have them. I'd love the day you asked the room “which consumer are you talking about?”

How Others See You

We tend not to value what comes naturally to us, because we've earned the ease. Other people see it more clearly than we do.

15.Ask five people. Text five people who know your work this one question: “What do you think I'm uniquely great at?” Paste their answers here word for word. Try to include someone from Nike and someone who knows you outside of work. Their answers, word for word Then tell me: what surprised you, and what was hard to read?

The Life You're Designing

You already painted it for me: up with the sun, a run, a slow breakfast, meaningful work from 11 to 3 or 4 where you're solving problems with a team, then dinner with Brian and bed at a normal time. More ease. More white space. Being where you want to be when you need to be there.

16.Is that still the picture? Now that you've had some space, what would you add, change, or protect even harder?

17.Your standards. These are the things you'll never trade away again, whoever you're working with or for. Think about how you want to be treated, how you want to work, and what you won't absorb anymore. These will be just as useful with a future client as with a future employer.

Who You're Becoming

Back in September of last year, you described a future Annie who had already made the decision and was so happy in her next life. Let's get to know her.

18.Describe her. How does she carry herself? How does she talk about her work? What does she say yes to, and what does she say no to without guilt?

19.When you imagine telling someone “this is what I do, and this is what it costs,” what comes up? Excitement, nerves, the voice that says who do you think you are? All of it is welcome here.

20.What old habit would be most likely to pull you back? Saying yes to everything, catching every dropped ball, the good day that makes the hard ones feel fine. Which one would be hardest to resist, even in a role you loved?

How We Build Together

21.What do you need from me to do your best work? More push, more pace, more permission, more space? Tell me where to lean in.

22.Six months from now, how will you know this was worth it? Not the metrics. The feeling.

23.What does your real capacity look like over the next six months? The holidays, your travel, Brian's season, the rest you still need. How many hours a week can you give this without it starting to feel like a job again?

Your answers go straight to Jessi. Write what you can — we'll go deeper together in the room.