Career support and new reading material
by Matt May
Hi, loyal readers. It’s been a while, but I have a really good excuse: I left the country.
I’ll explain in a second, but there is more important news, which is that I’m also back to career coaching, with an important twist. And I wrote a chapter for a new book: Digital Accessibility Ethics. Read on (or jump ahead) for my two new offerings and info on the book.
Bienvenido
Since the last newsletter, I’ve been quietly preparing for my own winter trial of living outside the country. I left in October for a couple months in Mexico, during which I’ve received my temporary residency, and I’ve decided to extend my winter stay into 2026. I mentioned last time that I wanted to work from wherever I choose, and residency allows me to stay and work, as long as my income is from outside the country.
A lot of the impetus behind this move is physiological. I’ve lived in the dark, wet winters of the Pacific northwest for almost 30 years now, and it’s given me a heavy dose of seasonal affective disorder. I decided this year to see how my body would respond to a warm, sunny winter, instead of the Big Dark. So far so good, as it turns out! I’m in a great neighborhood with amazing food, lots of activities and all the vitamin D I can absorb.

I’ve spent most of the first month getting settled and in vacation mode, and now I have started figuring out how to do work while in paradise. Whenever I go out, I’m giving my Spanish a workout. And I will say that it's a lot easier to disconnect completely, which is helping me break away from doomscrolling or watching TV news helplessly. My health, both mental and physical, is much improved, and that's a great base for me to get back to helping others.
Mi carrera es su carrera
I started offering open office hours back in 2017, for people working in accessibility, inclusive design, and related topics, as a way of supporting the community through the stressors inherent in the job. For the first few years, I'd say most of the folks who I talked with wanted to know about how to get into the field, or to nudge their jobs or their companies toward a more inclusive and equitable approach, against the headwinds of a hostile but honestly pretty ineffectual first Trump administration.
A couple years ago, the vibe shifted. Fewer and fewer people were looking for a way in. And more and more were talking about how hard it was to hang in there. By the time Trump had returned to office and launched a coordinated, sustained attack on DEI, many people were coming to me having been laid off, or on the way out; many who had felt reasonably safe in their career tracks were also now in crisis, seeing job openings dry up, their workloads increase, and/or their budgets cut.
Simply put: it's a hard time to be doing this work. A lot of people got into DEI-related work in tech because they saw the need, and found companies and organizations that sounded like they supported those efforts. Now, with a hostile administration, an AI onslaught and a seemingly inevitable market correction to come, they're seeing how easily the winds can change, and finding themselves stuck. People feel burned as much as burned out, and they're looking for ways to hang in there, to make some kind of progress with all the odds against them. But others are starting to realize that it's not worth it to stay in at all costs, and want to find something else to do with their life that's more in line with their values. Somewhere they can still move the needle.
Friends, I have been there. I've worked with hundreds of folks on their career trajectories. We've talked about hopes and dreams, but also realities, and incomes, and budgets, and reward systems, and management mentalities, and job markets, and macroeconomics. I've helped people work their way up within their organizations, building alliances and executive support so they can make change that sticks. And I've told people when the deck is stacked against them and I think they should move on.
I don't believe in staying in tech at all costs, and I think too many career coaches discount the possibility that someone can be happier and more effective (and maybe even more comfortable financially) doing something else, even if it's not a job at a big tech company. This is a matter of understanding one's own ethics, and what one is willing to accept. But once you find yourself fully in opposition to the work of your own company, you are at the point of moral injury, and that's an express train to burnout. Or sociopathy. Either way, it's worth a check-in.
Which brings me to my new offerings. Starting in December, I am offering a new, 6-session, one-on-one program for people who want to figure out their careers, with no prior attachment to the outcome. Once we figure out what you want to do with your life, we'll get into the work of how to do it. Maybe you want to recommit to the work you're doing; we'll take an inventory of what tools you have at your disposal, and go from there. Maybe you want to see what it's like working somewhere else in tech. Or you want to see what you could do in government, or a nonprofit space. Maybe you need a gap year. Maybe you want to sell bracelets on the beach. We can talk about your ethical stances, your red lines, your personal obligations, your budget, your resources, your risk tolerance. There will be homework! In the end, you will have a much clearer view of what you can do, ethically, to stay clothed, fed, and making a difference.
I worked in tech for 30 years. I have done this work for myself, and have drawn my own conclusion. Yours probably isn't "you should move to Mexico." But it's also not going to be "keep your head down and make sure the check clears."
The program is US$1000. Sessions can be weekly, or be spaced out for up to 3 months. If your organization offers reimbursement for career counseling or enrichment, I'll provide any necessary documentation.
I'm soft-launching this program today, and will start promoting it in time for the New Year self-improvement push. If my market research holds up, and I'm getting the word out, it will soon be more work than I can handle, which means two things: prices will go up, and I'll have a waitlist. If you're interested in doing this by the end of 2026, I've created a signup form for you. If you fill this out, you can lock in this price, and you'll be prioritized as new slots open up.
I am also offering paid office hours again, starting today. These are priced at $100 for 25 minutes, or $200 for 55 minutes. If you are looking for someone to talk through an organizational problem, dealing with a change in your career, or simply feeling overwhelmed and fried from trying to do the right thing, I've been working with folks like you for eight years, and can talk with you on a drop-in or recurring basis. I offer discounts for folks looking for long-term weekly or bi-weekly checkins. (These sessions are usually also reimbursable for corporate employee development or enrichment budgets.)
I offer a sliding scale, particularly for folks who are between jobs, working in academia, nonprofits, or freelancers. Please contact me for details. And, like I've done from the beginning, I have free office hours on Thursdays, subject to availability.
Libro
As I mentioned previously, I'm in another book! I wrote a chapter on burnout for the upcoming book, Digital Accessibility Ethics. It covers burnout among accessibility practitioners as an ethics issue for them as well as their employers, and provides advice for both to help prevent or mitigate burnout while clearing a path to progress.
The book itself features an incredible lineup of accessibility professionals, and I can't wait to get the finished product in my hands on March 26th. For now, you can take a look at the table of contents, the list of authors, and preorder the book today.
Horario de oficina
Office hours are available this week. I am now on Central time (UTC-6), and have availability most of this week for 25- to 50-minute paid sessions, and on Thursday for free 25-minute slots. (I know this Thursday is Thanksgiving in the US, but I'm in Mexico, so good news for non-USians who want to talk!) If you want to schedule a 15-minute informational about my program or paid office hours, I'm happy to do that, too.
To clarify: free office hours are really, actually free. If you're already a client and need to use one, that's okay. Once they're used up, new ones will pop up next week. I will never pitch you on any paid service during a free session.
- Free office hours (Thursdays)
- Paid coaching - 25 minutes
- Paid coaching - 55 minutes
- Schedule an informational meeting about 6-session career intensives
That's all. Have a great week.