I read something on Substack the other day about a guy who was 38 giving advice to those in their 30s and 20s.
His tone is very different than mine (lol), and I disagreed with some of the points he made, but the very first one struck a nerve. It read:
“When you turn 35, you’ll see the difference between those who took risks and those who didn’t.”
While I’m not 35 yet, it’s already ringing true.
I’ve started to see the separation between people who go for their goals and the people who watch them slip by.
I’m not saying that one group of people is better or more worthy than another.
The difference between the two is that there’s an internal fire within the people who go for it that causes them to make a change. The other accepts their fate—a comfortable, good enough life.
Risks shouldn’t be taken lightly or all of the time, of course. They should be intentional—usually coming from a soft whisper and then turning louder and louder.
The people who push down the voice telling them to go for it are the ones who stay exactly where they are.
I can say this because I was one of them.
If I didn’t take a risk and move to NYC, I probably would still be in San Francisco always wondering what if.
If I didn’t take the risk and leave my corporate job, I probably would be sitting at a dinner with my friends still complaining about politics and horrible bosses.
Risks don’t have to be huge leaps of faith—they usually start out much smaller until your nervous system feels safe to go bigger.
I believe that practicing risk taking now will set you up for more alignment, meaning, and achieving whatever goals you have set for yourself.
4 common reasons holding you back from taking risks (+ prompts to help you work through them)
According to my Notion CRM, I’ve talked to 127 people in the last year and a half (and honestly, it’s missing a lot of people).
These are some of the more common reasons I hear when people say they can’t take risks.
You don’t have time: You’re working a full-time job that requires 50+ hours per week. You literally don’t have time to work on anything else because you’re giving 110% to your job. Every other hour is spent on personal to-dos, socializing, or simply checking out with the latest Netflix show.
What is my long term vision in my career and life? How is my current work situation helping (or hurting) me in getting there?
What areas in my life are being sacrificed because of my work?
What’s my ideal working scenario and is that possible at my current company within the next 6 months?
How can I free up 5 hours per week to work on what I really want?
You don’t have energy: You might have actual hours to dedicate, but you don’t have the energy to do so. You started an idea, only to have life stuff pop up again, and it’s hard to get back on track. Or it could be the case that you don’t have an idea that’s exciting enough for you to keep going.
What habits or rituals can I incorporate weekly to increase my energy?
Who do I want to help most and why is helping them important to me?
How can I make my side project / career experiment more fun? (Switching up the environment? Partnering with a friend?)
You don’t have confidence: You’re afraid of doing something different because you’re not sure how it’ll work. You second guess yourself and have trouble putting your work in front of the people who actually need it because you’ve never done it before.
What mindset block is holding me back? (Fear of failure, fear of what other people think, imposter syndrome, perfectionism, or something else?)
How can I reframe my thoughts to something more positive that will help me reach my goal?
How can I develop a support system of people who are doing similar things?
You don’t have the means: You’re responsible for finances for yourself or your family. Leaving something stable means risking your lifestyle or even your basic needs. You don’t experiment because you feel like this is the only way to ensure safety.
What is my current lifestyle costing me? What are my bare minimum basic needs?
What if working on a career experiment made you more money? How would you feel?
Final thoughts
Risk-taking isn't about being fearless. It's about being curious enough to try, even when you're scared and building a life that's big enough to hold all of who you are, not just the version of you that plays it safe.
Your turn
Vote below and reply back to this email with a risk you’ve been thinking about taking.
Which reason is holding you back from taking risks?
✨ Weekly Feels
I’ve been thinking a lot about (1) systems and (2) future offers that play to my strengths and also tie into something I enjoy.
On the systems front, I am having fun with Zapier and learning more integrating AI into my work to handle manual tasks. I have Zapier workflows that automatically do things like add a lead to my Notion CRM after someone books a call with me, send onboarding emails once a client pays, and more.
I’ll be writing a newsletter on this soon and featuring other solopreneur’s workflows!

Some of my Zapier workflows
On the offers front, I’m getting ready for my 2nd cohort of Just Start. I’m making a lot of tweaks this time around to make it even more valuable and sustainable with a full-time job. Things like templates to craft your outreach and surveys, pre-recorded lessons to save live time for workshopping, and more.
I’m also tinkering with a few other ideas. If you want to help shape them, please help me by filling out one (or both) of my surveys below 🙂
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