Day-to-day, there are two topics that I am asked about most: design and working for myself.

If you're reading this, it's likely that you are a professional designer. If you're reading this in your inbox, it's because you're a designer who signed up to get one of my books, attended a training program, signed up for CDO School, joined a webinar, etc.

While a lot of people ask me questions about design careers, an equal number of people want to know how to make their own money. They are curious about anything from strategy and operations, to product development and audience building.

When I first started working for myself in 2019, everything I did was delivered under the banner of Second Wave Dive. All my training cohorts, the content I produced, the tools and frameworks I created… all of it was done under the SWD banner. Professionally, I don’t fit nicely into any traditional professional box. I make software, teach, coach, consult. My background is interdisciplinary and I wanted to run a company that allowed me to do that.

SWD was just the business name of me. From the start, it has always been creative studio that works much like an incubator. I make software, offer courses, write books, provide consulting and coaching services. It's always been an exploration in making good money, starting new companies, and working creatively in unconventional ways.

While a lot of people ask about how I do this, it's always via a DM. And since you're likely a designer, it felt really strange to talk about working for yourself stuff alongside the design stuff. After all, you only signed up for one of those topics.

So, I decided that if I wanted to write, talk, and share content about running a company of one, I had to make some changes.

Heavy behind the scenes work began in 2023

In 2023, I began moving all the designer specific materials, courses, and programs over to a new brand; CDO School. At the same time, I was developing other programs and content under new brands like Jump Ship! and The Strategy Studio.

Pretty much everyone I spoke to told me this was a bad idea.

They told me that creating multiple things and multiple brands would require a lot of work, a ton of back-end changes, and it would "dilute" what I'm known for. It also meant I wouldn't have the time to do much in terms of writing, talking and sharing.

They were right, but my instincts told me it was the right thing to do.

For the last 18 months, I've updated all aspects of my operations, all while trying to keep steady money coming in. I've never shared this in public, but here's what's been happening:

  • Updated all my banking and accounting
  • Moved all website content from multiple Squarespace sites to multiple Ghost sites
  • Created all new brand materials for social and marketing
  • Developed new voices and tones for the different brands
  • Sorted out what the business model and strategies were for each

It's been a long road, but all of this work has been done to get to this day. I'm ready to share.

My content has three separate homes

Starting today, I'll be showing up in your inbox under three different banners; Second Wave Dive, CDO School, and Jump Ship! Each banner has a specific focus.

Second Wave Dive: Scale your solo business by running multiple brands

  • Materials, tips, lessons, thoughts, etc. about building long-term sustainable independent work, developing micro-businesses, and creative projects.

CDO School: Get the skills you didn't get in design school

  • Practical tips to grow your design career, insights from everyday designers doing the work, what's happening inside CDO School, and making influence more actionable and achievable.
  • A complete library for experienced designers and leaders to make confident decisions in anything but design, A year-long learning network for senior designers and leaders, and using AI to create your Design Leadership OS.

Jump Ship!: Build tools with AI to grow your business

  • Stories about self-employed people using AI to get more customers, ditch expensive subscriptions, and make more money

Here's what this means for you

You are already subscribed to Second Wave Dive and CDO School. If you're into design stuff and making your own money stuff, expect to see more content from me on a very regular basis.

  • To update your Second Wave Dive subscription, click here.
  • To update your CDO School subscription, click here.

You are not subscribed to Jump Ship! If you want to make your own money, do your own thing, and run a company of one, this is for you.