Debbie Millman: "Courage to take a step into the unknown is the birthplace of creativity."

I want you to imagine something. In fact, if it’s easy, grab a pen and write it down: It’s winter 2031, ten years from today. What does your life look like? Be very specific here. Who do you live with? What is your job? What shoes are you wearing?

Now keep this. It will be helpful as you listen to today's episode of Hello Monday.

This is the ten-year plan. It’s an exercise I talked about with today’s guest, Debbie Millman. 

Debbie is living proof that articulating your dreams and planning for them can lead to great things. During her 20 years as president of Sterling Brands, she worked on logos you’d recognize, like Burger King and 7Up. She’s written six books, and she helped found the world’s first masters in branding program. Her artwork has been shown around the world. 

And for more than 15 years, she has hosted one of my favorite podcasts, Design Matters. She interviews other people about how they navigate creative and powerful careers. So, in this episode, I have attempted to distill her formula for success. 

You can download the episode to hear about it, or listen to it below. Then, please, share your own thoughts and tag them #HelloMonday so I can jump into the conversation.

??Here are some highlights….

On confidence: "I define confidence now as the successful repetition of any endeavor."

On life: "I wish I had worried less. I remember after leaving the first company that I created with my partner back in the early nineties, I left. And I remember thinking at that time that I was probably unemployable. I'm 32, and I am a has-been and I'm never going to get another job again. I really thought that, and my career had barely started. I've spent a good amount of time worrying about not being good enough. And that fear keeping me back from trying things, because I was so afraid of rejection of failure.

On feedback and social media: "Seth Godin's book, The Practice, really suggests looking at your work as a practice to do every day and thinking about what makes you feel alive as opposed to what is going to get the most likes or clicks or feedback. I do think that the work itself is hard to evaluate without feedback. And I think as a culture, now, we expect and anticipate that feedback in everything fairly instantly. And so that feedback, while it gives us that sense of happiness in the moment, it's a hit of dopamine. It's really ultimately thwarting real breakthroughs because we then really kowtow to that feedback."

Advice from a memoirist she admires, Dani Shapiro: "She said she felt that ultimately confidence was something that only came after courage, that it was much more important to have courage, to take that first step into the unknown, than to be able to just manifest confidence through some sort of motivational inner language. I do feel that that's true. Courage to take a step into the unknown is really the birthplace of creativity.

On creating a personal ten-year plan: "There's something about envisioning and declaring what you want that is very powerful. I do think it's a little bit of magic, too. But it's mostly about articulating and declaring what you feel you're worthy of being able to achieve."

On imagining the future at a challenging moment in her career: "We tend to think about what we know. It's very hard to imagine more. It's much easier...for us to imagine having less. We don't think of possibilities coming in. We only think of opportunities going away. And I was really worried that without having that security, that I'd have nothing to replace it with. Never considering that any number of things could manifest that I've had that I've had no idea about at that time."

?? Office Hours: Taking your questions

So what do you imagine for your own life in a decade? This week on Office Hours, producer Sarah Storm and I will stitch together our own ideas, and we invite you to join us.

If you haven't been to Office Hours, it's our coffee break, quite literally--a time to get together with listeners for a little community. Sarah and I go live every Wednesday at 3pm EST to talk about the week's episode, get ideas for the future shows, and generally catch up. We've got a steady group of listeners who join us every week and quite a few people who pop in occasionally. Sometimes we invite guests; sometimes we keep it very informal. If you have an idea for a guest, or thoughts on your own ten-year plan, or you just want to come see who puts the show together, RSVP below or email us for a link at hellomonday@linkedin.com.