A 3-part email template that helped me leave my comfort zone and start a company in college
A guide for you to start something right now
“There comes a time in every life when the past recedes and the future opens. It’s that moment when you turn to face the unknown. Some will turn back to what they already know. Some will walk straight ahead into uncertainty. I can’t tell you which one is right. But I can tell you which one is more fun.” — Phil H. Knight
In his book, The Untethered Soul, Michael A. Singer describes two clear-cut ways to live:
- You can devote your life to staying within your comfort zone by making sure everything fits within your mental model of the world
- Or you can devote your life to freeing yourself from the limits of your model
To understand this better, he uses the example of an invisible electric fence. As someone who loves dogs (and cats!), I found this analogy a bit… shocking. But that’s exactly why it stuck with me.
The invisible electric fence
Imagine for a moment that you’re a dog. You’re the living definition of joy — running, jumping, and exploring every nook and cranny. You dash outside and just when you thought you could explore what’s beyond the yard — ZAP! — discomfort courses through your body and you stop dead in your tracks.
As it turns out, you’ve discovered a limit to where you can run. Every time you reach that limit you get a shock. And it hurts.
Now that you know what these shocks feel like, you experience fear and discomfort whenever you approach the edges. You feel insecure because you find that the edges are everywhere. And now it’s a depressing day because even though you used to roam free, you decide you’ll never try to leave the yard again.
This is your life
Even though we’re not actually experiencing any electric shocks as humans, we each deal with something similar and all too real — our comfort zone. In our minds, we roam around a familiar and well-trodden yard. And whether we’re aware of it or not, the edges of that yard guide our decisions every day.
When we hit these edges we feel all the feelings we don’t want to feel: afraid, alone, anxious, guilty, insecure, overwhelmed, rejected, sad, self-conscious, weak. We pull back from the discomfort. We try to find safety. We stop trying.
Imagine yourself as that dog again, but this time, you’re determined to be free. You sit right there at the edge of the yard where your electric collar starts vibrating, and you refuse to back off. Every minute you are inching forward a bit more, getting used to the feeling.
Eventually, you’ll get out. As long as you’re ready and willing to handle the discomfort, there’s not a chance in the world that you won’t. You’ll realize that your collar can’t hurt you, it’s just uncomfortable.
Instead of fighting to stay within your comfort zone, what if you saw that these edges actually point your way to freedom?
Like a trained athlete, you know exactly how to handle the moment as soon as you come up against an edge — you relax, lean in, and push through.
If you’re willing to go beyond your comfort zone you’ll be free to go anywhere. You’ll never stop pushing past your limits instead of just “getting by” or surviving the next day. You’ll confront all the feelings you don’t want to feel. You’ll start connecting, creating, learning, and failing.
You’ll be free to experience all of life.
A tool for stepping through
For 9 years, I competed in a sport called fencing (ironic, I know). I experienced some of my highest highs and lowest lows competing around the world. By my junior year in college, however, I was in the depths of an existential crisis — I wanted to put the time I spent training towards something that would improve people’s quality of life. I wanted to build something much greater than myself, but I was terrified of all the edges I would come up against. I was afraid of who I would have to become.
I was that sad dog, fumbling for months, feeling like an impostor and stewing in my own doubts. What I finally did that allowed me to leave my comfort zone and start my first company was to take my proverbial hat and throw it over the fence. As the saying goes, I committed myself to the task so that there was no backing out. I had no choice but to follow through.
Every month I sent out a 3-part email to people in my life listing out:
1. What I’d been up to
2. What my goals were with a timeline
3. What I needed help with
Then I made sure to keep in touch with new connections through this email to both keep myself accountable and ask others for help. This list grew from 5 to 300 people within 1.5 years with the velocity of work and progress it created. The more people I emailed, the more powerful the motivation.
By publicly stating what I was going to work on and what goals I was aiming to hit, I was able to create painful consequences for not producing results or achieving something monumental. In order to not give up, to not stop trying, I had to go beyond my comfort zone.
I wasn’t sure that I could reach my goals each time, but I was motivated more than ever to challenge myself and find a way to push through to the other side. I found that often times, it’s the commitment that creates the solution. Having prominent investors, entrepreneurs, athletes, and industry leaders on the list only made the effect stronger.
The email template
So here it is, the email template that changed my life. I hope it changes yours too:
I was wondering if you wanted to be on my [Frequency] update email list (please feel free to say no). This is the way I keep myself accountable and also keep in touch with important people who have helped me with [Project]. I’m very grateful for your advice and support.
[Project/Company Name] [Month] [Year] Progress Update
Major Goals Accomplished (Last [# Weeks/Months])
- For each section, write 3–5 bullet points (maximum).
- Avoid going over a single email line for each bullet (1–2 sentences).
- Were you able to accomplish the goals you set for yourself last month?
- Did you have any unexpected wins?
- Be honest, precise, and proud of the hard work you’ve done.
Major Goals to Accomplish (Next [# Weeks/Months])
- With new clarity for your next steps, set new goals for yourself and a timeline for which you want to accomplish those goals.
- If you’re lacking clarity, write questions you will answer by your next update.
- Set goals that require going out of your comfort zone to reach.
- If you only set goals that you know you can reach, then nothing has to change in your life.
- If you commit to a goal that you currently cannot or don’t know how to reach then you will have to change in order to become the person who can do it.
- What do you need help with right now in order to accomplish your goals?
- This section is the lifeblood of your email, make it bold and a different color.
- It allows people to engage in what you’re up to and connect you with others.
- Personalize this section to what’s relevant to the individuals you are emailing.
Thank you so much for reading. I really appreciate being able to share these goals and challenges. Let me know if I can help you in any way.
Why this works
I recommend this template because of a few reasons:
- A simple conversation starter
I found that adding my monthly update emails to the bottom of initial email interactions with people was a fantastic conversation starter. It was a simple, quick read to get someone up to speed about what I’m working on and how far along I am.
- Regular updates cultivate relationships
Regularity has a powerful psychological impact. Whether it’s to family and friends, or to investors and advisors, consistent updates keep your work front of mind. By being open about what I was dealing with and learning, I was also able to help others who were going through similar challenges.
- Seeing the power of asking for help
Too often, we stop ourselves from asking for help out of fear of being judged, looking bad, and convincing ourselves that we don’t need it. I’ve been completely and utterly blown away each time by the sheer generosity of the people around me. Relationships are never numbers, but I trust that you will read this as encouragement: These updates consistently had 80%+ open rates and 20%+ response rates.
- Self-discipline + progress = gratitude & inspiration
I want your inbox to be flooded with countless words of support, advice, and connections because you have so much to offer the world. Don’t wait to start because I guarantee that if you put yourself up for the challenge and lean into your edges, incredible things will happen. You will meet people who will change your life again and again. Their endless love and support will remind you that we’re all in this together, spinning on a planet in the middle of nowhere. You will feel a new profound sense of gratitude that will push you to work harder and give more back to your community. And in the process, you will inspire others, so that they may find the same.
“Try new things, step out of your comfort zone, take risks, do things in ways you’ve never done them before, ask for help, surround yourself with self-actualized people, become obsessed with the fact that you have one go-round on this planet as the you that is you, and realize how precious and important it is not to squander that.”—Jen Sincero
One last thing…
Thank you so much for reading this. If you liked this article, share it with someone who might benefit from reading it too. Best of luck and add me to your email update list: email@example.com
I’d love to read your progress updates and I can’t wait to see who you become.