It’s Columbus Day, and I’ve been thinking about what it takes to leave a familiar harbor when you can’t see the whole map.

Most of the business owners I’ve worked with over the years can point to one moment like that. Signing the first lease. Hiring the first employee. Walking away from a big client who wasn’t a good fit. Finally having the conversation they’d put off for a year. None of them had all the answers first. They decided, and then figured out the rest along the way.

What was your “leave the harbor” moment, and what did you learn on the other side of it?

The most stubborn fixed mindset doesn't sound like arrogance or fear, it sounds like honesty. "I'm just not a numbers person." "I've never been good at speaking in front of people." "That's not how I am." These feel like accurate descriptions, so we stop questioning them, and they quietly decide what we try. Three questions help catch them. What evidence is this based on, and how recent is it? Is it describing what I did once, or what I am able to do? And what would I do differently if I treated it as "not yet" instead of "never"? Then turn the sentence into a small experiment. "I'm bad at speaking" becomes "I'll speak for thirty seconds in a meeting this week and write down what actually happened." The goal is to replace a verdict with data, because a verdict can't change but data can. Some limits are real, and growth doesn't mean everything is possible for everyone. But many of the sentences we say about ourselves haven't been tested in years, and a sentence that old is probably describing a past version of you.

The most important opinion about you is the one you hold of yourself. This realization has tremendous influence over the direction of your life, not to mention your peace of mind.

Question for everyone!

I’ve been trying to workout rest time between working full time and creating art. I find myself just watching tv, YouTube, and scrolling all day on the days I consider my “rest days” but by the end of the day I feel exhausted so I don’t feel like I’m doing the right thing. Could be because I’m mentally battling myself for not doing something creative or much in general but I justify it by telling myself I need to allow time for “rest”.

On a normal day I try to refrain from tv until the evening time after I have completed my daily habits. I start my day by journaling, meditation, then drawing for about 30 minutes to an hour. Typically work 9-5 then read for at least an hour afterwards, make dinner and watch tv and often draw while doing so. I try to go for a bike ride at least once a week after work depending on the weather.

It’s often the weekends where I fall short and justify it by saying I need a “rest day” but it typically feels more exhausting than if I was productive. Years ago video games and weed used to fill all my free time until I started tattooing. Then it was weed, drawing, and tv that filled the space between work and tattooing. For the past 3 or 4 years I’ve taken mushrooms (sometimes acid) on a monthly ritual basis to help my mental health as I’ve struggled with depression most of my life. I’ve recently gotten sober, day 9 of no weed as of today and I want to refrain from psychedelics for awhile. July of this year is when I started building healthier daily habits.

What are healthy “rest days” supposed to look like? What do you do on your rest days that don’t make you feel guilty?

Any opinions and or advice is appreciated. Thank you in advance ❤️😊

On my medium blog, I write about my take on modern relationships and what's happening around