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 - learn how to stay small and run a successful company of one.
In this newsletter, you get:
- Materials, tips, lessons, thoughts, etc. about building long-term sustainable independent work, developing micro-businesses, and creative projects.
- Topics like Behind the Scenes, Positioning Yourself as the Expert, Finding Paying Customers, Tools, and more.
CDO School - get the skills you didn't get in design school
In this newsletter, you get:
- Practical tips to grow your career, insights from everyday designers doing the work, what's happening inside CDO School, and making influence more actionable and achievable.
- Topics like Business Acumen, Operations, Stakeholder Management, Communications, Strategy, Emotional Intelligence, Personal Growth, Leading People, and more.
Jump Ship! - start a company of one with AI co-founders
In 2023 and 2024, I ran experimental workshops under the Jump Ship! name as a collaboration with my pal Greg Storey. Soon, we're launching something entirely new under the Jump Ship! name.
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.
- To be the first to know about Jump Ship!, join the waitlist here.