In August 2011, I was waiting for my California Bar results. I knew I wanted to build my own practice, so I spent that time talking with small business owners.
One of the questions that I asked every business owner was,
What do you do now in your business that you wish you had started sooner?
One answer has stuck with me ever since.
A friend who ran a tattoo shop said,
Start a notebook where you record all the stupid sh*t you do that you don’t want to repeat. And then every day, write in it or read it.
After I passed the Bar, he handed me a Moleskine notebook. Inside the cover, he wrote:
Congrats. Here’s your own Sh*t I’ll Never Do Again book. Fill it up.
Fourteen years and several notebooks later, that advice has shaped almost everything about how I run my business.
- It’s helped me see what client situations repeat, and how to stop them.
- It’s helped me revise my contract so it reflects how I actually work.
- It’s helped me understand where I needed better boundaries and better language.
Sometimes when I read those early entries, it’s painful. Some experiments in there were destined to fail.
And I’m sure years from now, when I read some of my recent entries, I’ll shake my head. And wonder why I ever thought that was a good idea.
I credit much of the progress I made in my first year in business to this notebook.
Because the real power of the notebook wasn’t just in writing down what went wrong. It was in what how I learned from it. Especially when emotions were high, timelines were tight, or expectations didn’t align.
The act of reflecting and writing these lessons ingrained them into me. There were times when I started to do something, and the image of those pages popped into my mind. That image gave me pause, so I could stop and correct course.
This notebook has helped me be a better lawyer and businesswoman.
And while it has helped many parts of my business, it’s made the biggest impact on my client relationships.
When misunderstandings arose, I took the time to figure out what caused them. When all hell broke loose, I reflected on where it started and how I could prevent it from happening again.
Because it has become my blueprint for what and how I need to change to improve.
And that’s why this notebook has been so powerful for me. This notebook has directly improved every aspect of working with my clients.
One place where it’s made a huge impact is with the contract I give clients.
I’m one of those nerds who find contracts exciting. They are my jam. But I know that my clients don’t feel the same way.
And this notebook has helped me treat my contract as a living document. One that’s updated, changed, and modified based on things I learn and client feedback.
Contracts shouldn’t be written and then used robotically. You shouldn’t be filling in blanks. Or never update them once you create them.
Your contract should stay current with your business, what you learn, and client feedback.
And anytime you have a project that leaves you feeling used or unappreciated, you should decide if a tweak to your contract would help.
- Did this happen because you failed to enforce part of your contract?
- Is this something that your contract doesn’t cover?
- Is this something your contract covers vaguely?
- Do you need to change how you talk about your contract with clients?
I encourage you to change your mindset around your client contract. And to think about it as a living, breathing document.
One that changes and grows as your business does. And in turn, will make sure that you won’t have to repeat the same mistakes again.
If you’ve been noticing patterns in your own client relationships, and you’re ready to make changes that actually stick, then enter your email below to grab my free No Surprises Contract Checklist.

Hi! I’m Kiff! I’m your friendly legal eagle (and licensed attorney).
My goal is to add ease to the legalese. And because I think basic legal resources should be available to every creative, I create a lot of free content.
If I’ve created something that has helped inject a little ease into your creative business and you would like to say “thank you”, you can make a contribution here.
If you’d like to hear more from me, I’d love to pop into your inbox every Friday morning to share additional ways to cut through the red tape and inject a little ease.
Get tips from your friendly legal eagle in your inbox…
Your privacy is important to us. Learn how we protect it here.