Dillan Taylor
My favorite question to ask people
I ask questions for a living. Coaching, podcasts, writing… What makes a low-quality question? In my mind, it’s one that can be answered...
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Blog
Dillan Taylor
Feb 23, 20233 min read
2023 feedback review: my results (part 2)
Connor’s bachelor party in the mountains, April 2022. Earlier this week I shared the biggest criticisms I took away from my annual...
Dillan Taylor
Jun 13, 20227 min read
3 things I’ve learned after 1000 coaching sessions
The first coaching session I ever ran was on June 26, 2020. A friend agreed to be my first guinea pig. I began coaching my buddies for...
Dillan Taylor
Apr 14, 20222 min read
You can do it (actually)
Here’s a self-improvement cliche: You are capable of so much more than you think. I check in with my coaching clients every two months or...
Dillan Taylor
Mar 28, 20222 min read
Startups suck
That sounds harsh. Here’s what I mean. When I visited my friends in Philly this January, I walked one of them to the train station. We...
Dillan Taylor
Mar 25, 20222 min read
Next level
I’m shifting my business. It’s scary. 2021 was the year of building my one-on-one coaching practice from scratch. Mission accomplished....
Dillan Taylor
Mar 14, 20221 min read
Ideas vs. execution
I have a running list of business ideas in my Notes app. I’ve done nothing with 99% of them. People can be super protective of their...
Dillan Taylor
Mar 11, 20221 min read
Twitter rd. 2
Here we go again. @DillTho Follow the kid.
Dillan Taylor
Feb 25, 20221 min read
Boundaries
If we set boundaries, people will meet them. I’ve been slowing things way down in my business this year. Everything out of necessity. I...
Dillan Taylor
Jan 27, 20222 min read
The 10 million dollar question
I doubt that’s actually $10m. I got to ask one of my favorite questions yesterday. In a session, a client told me he wanted to take more...
Dillan Taylor
Jan 24, 20221 min read
You don’t have to 10x
Not a coaching client. I check in with my coaching clients regularly. I’ll ask things like: Where do you feel like you’re at? What have...
Dillan Taylor
Jan 19, 20222 min read
Should we be able to talk about money?
Money can be a sticky thing. There’s this age-old taboo that says we shouldn’t talk about money or ask people about theirs. I think we...
Dillan Taylor
Jan 5, 20221 min read
What’s your garden look like?
I did a fun exercise with a client yesterday. I had him write out a typical, average day in his life—morning routine, workflow,...
Dillan Taylor
Nov 29, 20213 min read
A weird key to success
It’s strange to claim that I’m successful. But I certainly feel like I am. As we’ve heard many times before, the word “success” means...
Dillan Taylor
Nov 27, 20212 min read
It’s not a “gift”
During Thanksgiving lunch this week, one of my family members complimented me when asking about my business. The past three months have...
Dillan Taylor
Sep 27, 20212 min read
I’m just a reject
I’ve been rejected a lot this year. This was to be expected as I launched my coaching career, but reflecting back on the number of No’s...
Dillan Taylor
Jul 17, 20213 min read
Why I don’t promote my business
In the past week, two different people have asked me why I don’t use my blog or newsletter to promote my business or try to get leads....
Dillan Taylor
Jul 14, 20212 min read
Certified Insight Coach
Today, I graduate from my 16-week coaching academy. In this time, I’ve received a ridiculous amount of training, made friends with...
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