Hello! Who are you?
Hello, world 🙂. My name is Bill Lennan.
I live in Silicon Valley, am the co-founder of a mental wellness education company, and this is my 5th+ career path. Previously, I’ve spent 25 years running software teams, was a realtor, and was a Ferrari mechanic out of college.
I’m a happy parent, my sons are 21 and 18, their mom and I have the best divorce on the planet. I also have a girlfriend who’s amazing.
I’m passionate about having adventures, helping people, and staying fit.
And yes, I’m very happy. Life is an interesting series of challenges - I choose to see them as adventure possibilities.
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What is your struggle and when did it start?
I struggled for decades with social anxiety.
I was afraid to talk with strangers, afraid of crowds, and even afraid to get vulnerable with my friends.
My anxiety had a few causes. Sadly, a big part was what my mom told me growing up - that I should not be in conversations unless invited and that my perspective wasn’t valuable. She also had challenges controlling her temper and would scream criticisms - which I learned to avoid by not talking.
I was always happy to work and choose roles that didn’t require deep conversations. And as my software career advanced, it became clear that my fear of talking with people was also crippling my career progress.
How did this struggle make you feel at your worst moments?
At its worst, my social anxiety had me considering ending my life.
The combination of relationship struggles, career frustration, and no perceivable end to the pain was an overwhelming darkness. I drank every day to manage.
No one knew of my struggles. Even my wife didn’t know how much I was struggling. Part of the challenge was my inability to communicate effectively with her.
Looking back, I can see how my fears of criticism, feelings of scarcity, and lack of communication skills kept me in a trap of my own construction.
I thought I was the only person with this kind of struggle.
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Was there a moment when you started to turn things around?
The turnaround happened due to a series of tiny steps.
My wife insisted that we see a therapist. Our marriage was a shambles, neither of us was happy, and we were both afraid of our pain impacting our kids.
The therapist recognized my social anxiety. We had a series of sessions with her, both together and separately.
One day when it was just me, she shared that my communication problem could be solved much more effectively at a Landmark workshop than by working with her.
She didn’t elaborate beyond giving me their website. I immediately trusted her advice because it meant substantially less income for her. I signed up the next day.
At the workshop, I realized that many other people had the same or worse struggles. In a group of 200 people, I was just another face, listening, learning, and finding small freedoms as our mental models changed.
At that workshop, I realized that learning and practicing skills was how I could achieve freedom from my fears. I was able to point at specific areas (i.e. giving presentations) where learning specific skills (PowerPoint) would make that area achievable.
Taking this skills approach, I started learning baby steps and practicing better communication skills at work and at home with people I knew. I also learned how to present effectively which opened up more work opportunities.
It took a bit longer to get comfortable talking with strangers. And again, I started with learning baby steps. My first step was simply asking the barista at Starbucks how their day was going. This sounds trivial but I can remember the sweaty fear I felt the first few times.
I’ve realized that doing the behavior gave me the evidence and ultimately confidence that I could be comfortable in any communication situation.
What steps did you take to overcome your struggle?
My first big “aha” moment was seeing all the other people in the seminar who were also struggling to communicate. I had been ashamed that this communication problem was uniquely mine and hadn’t imagined a place where I was just another shy introvert among hundreds. Seeing that others shared my problem and that they were also working to reverse the challenge was enlightening.
The second shift happened after two weeks of practice starting conversations. This was an exercise that a friend helped me to create - asking a barista (or any retail worker) how their day was going. At two weeks, I realized how easy this exercise had become, quite a contrast from the sweaty starting point.
In just two weeks, maybe 20 repetitions, I’d had a huge shift in my confidence (even though they were only 2-minute conversations).
I still practice this today, a dozen years after that epiphany.
The next shift was understanding the value of being interested in conversations vs. being interesting. I can 100% control my level of interest in someone else, just by being curious and prompting them to share by asking questions.
Early on, this let me avoid talking about myself and still have conversations. It also made people want to talk with me more - because people enjoy talking about themselves. I used this for business networking, social situations, and even dating.
Since then, I’ve learned, practiced, and become very comfortable with presenting, leading trainings, and even public speaking.
One of the strategies that really helped me succeed was using “baby steps”. Figuring out how to give myself an achievable challenge, even if the action seemed trivial.
Asking baristas how their day is going - seems trivial but it was all I could manage. My first presentations were to three people. My first public speaking lasted five minutes. When we can break down the learning into tiny increments, every piece is achievable.
Have you shared any of this with people around you in real life?
Yes!! I’ve taught this approach to dozens of people ranging from teens to mid-career professionals.
Watching students go from being nervous about meeting strangers at college to being excited about possibilities as they practice is delightful.
Hearing professionals share how networking has become possible and interviews become easy is another highly rewarding outcome.
If you could give a single piece of advice to someone else that struggles, what would that be?
We all struggle, it’s part of being human.
Once we can accept the normality of struggle, we can stop self-criticism which just makes things worse.
Getting out of struggle is a two-part recipe: our beliefs and our skills. When we can upgrade our beliefs and start learning and improving skills, the struggles become simple activities that we take for granted.
As babies, walking was a struggle but now we take it for granted. I can remember struggling with multiplication and division - both of which I do in my head now.
Struggle is just a sign that we need to learn and practice new skills, our beliefs usually change in the process.
What have been the most influential books, podcasts, YouTube channels, or other resources for you?
- Landmark Education.
- Awaken the Giant Within by Tony Robbins.
- DBT Skills for Adolescents by Linehan, Miller, Rathus.
DBT is the leading clinical intervention and should be taught preventatively to everyone. I use these skills every day to improve my emotional resilience, stay on task, manage my energy, and communicate effectively.
- Outliers by Malcolm Gladwell.
- Finite and Infinite Games by James Carse.
Where can we go to learn more about you?
💡 By the way: If you want to start feeling better and more productive, I've condensed the information of 100's of our articles into a 10-step mental health cheat sheet here. 👇
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