3 Key Lessons from “How to Design a Life”
This is a summary of the Tim Ferriss Show podcast episode #214 and reposted on Nov 5th, 2021
For those of you who are not familiar with Debbie Millman, she has been described as “one of the most influential designers working today,” by Graphic Design USA. Among many of her accomplishments this one really stood out…
"At one point, if you walked into any given grocery store or supermarket, anything like that, she had a hand in about 20 percent of everything you might see or touch".
In this podcast, Debbie describes some of the difficult career and life decisions she's had to make and she provides many tips and insights into how she handled them. It’s easy to forget all the great points that Debbie shares in this podcast, so the intention of this post is to capture the ones that really resonated with me. To listen to the full podcast click here. To read the official podcast transcript click here.
Lesson 1: Create a 10 year plan for a remarkable life
Debbie describes an exercise that she learned from Milton Glaser in which you envision and write out what your life would be like in 5 or 10 years. She recommends that we dream as big as we can with no fear of failing - don’t edit anything out. She goes on to explain that being as vivid and detail oriented as possible is positively correlated to the likelihood of that future coming true.
For example, describe your future spouse, kids or pets, if that is what you want - what are they like? How do you feel? What is a typical day like? What do you do for work? Get as detailed as possible even down to the type of sheets you will be sleeping on. It’s that simple. Once the document is completed, re-read it every year.
Lesson 2: We don’t think enough about the upside
It’s never easy to make a decision to leave the conventional path to success. In Debbie’s case she was deciding between an opportunity to become the CEO of a company or pursuing a less clear but equally important personal mission. The conventional path would provide a stable career, lots of money and social approval; however, this was not the path she had envisioned for herself.
As she was considering her options, she expressed her fears with an analogy:
“…I was in a trapeze, rather than let go the of trapeze and do something else, every crook of my body holding on to some other trapeze… had the sense of if I’m doing enough, I’m not worthy, if I’m not making enough, I’m not worthy, if I’m not producing enough, I’m not worthy... Suddenly, I not just let go of the trapeze but let go of the entire apparatus”
Debbie shares that she learned two things from this experience:
“Most people live in a world of scarcity… we don’t think about all the possibilities of things that could come up if we give ourselves openings to receive them...I have all these new things that I’m doing that I never would have thought possible”
“Hard decisions are only hard when you’re in the process of making them. Once you make them, they are not hard anymore. Then it’s just life and freedom.”
Lesson 3: Rely on courage rather than confidence
How do you know you’re making the right decisions in life? Especially when the choices seem so dire and consequential. This might sound familiar, in your mind you set a goal for instance if you’ve amassed a financial cushion of $500k maybe that’s when you make a radical career transition. Debbie warns us:
“I also think that if you’re waiting for something to feel right before you do it, if you’re waiting for a sense of security or confidence, that those things are sort of like being on a hedonistic treadmill”
The concern is once we hit that cushion of $500k, we’ll probably increase that threshold to $1M and so on and so on. On top of that, we’re likely to doubt ourselves and feel like we lack the confidence to make the tough decision. Debbie goes on to quote Dani Shapiro:
“...confidence is highly, highly overrated… But in order to take that first step you need courage, and that’s much more important than confidence”
Personal thoughts:
The podcast encouraged me to take action right away and start writing about my future life. I’m a big fan of vision boards but prior to this podcast, I have not written out the future in great detail. I found it to be a fun and inspiring exercise.
On the topic of upside potential, I’m definitely someone who is more focused on all the things that could go wrong, and thinking of ways to mitigate all the downside risk. I’m still working on not only preparing for the worst but also spending an equal amount of energy imagining the enormous upside if everything goes well.
Finally, I couldn’t agree more with Debbie and Dani about relying on courage rather than confidence. I recently had a difficult decision to make, although the stakes were much lower for me (my other option was not a CEO role). In my case I was still leaving a job to pursue a less defined personal path. As I reflect back, I was definitely not confident in my choice but I’m glad that somehow I was able to muster up the courage to make my choice.