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This Career Pivot Playbook features Gail K., a former law firm accountant of 16 years and the writer behind The Old Black Lady Chronicles, a newsletter built on one idea most people trying to build an audience miss…

You do not need a big audience to make money. You need one clear offer, and the nerve to sell it.

She did not leave because the job wasn’t paying. She was highly compensated, well established, sixteen years deep. On paper, it was the safe choice.

Then a moment in her boss's office made the decision for her: stay quiet and small in a company that didn’t value her worth, or bet on herself.

What she did next is the playbook.

Inside, Gail breaks down how she went from corporate accountant to business and money coach, then pivoted again to Substack. She explains why the beginning was slow, and what actually turned it around.

She is clear on community, consistency, and why treating a new platform like moving to a new city beats chasing numbers.

She also shares about the note that changed everything, and how she now teaches women over 50 to turn their own experience into something sellable.

If you have the wisdom and the experience but haven’t yet turned it into something of your own, this one is for you.

A public archive of modern career blueprints…

Most careers no longer follow a straight line.

People pivot gradually.
They extend their work beyond institutions.
They combine roles, platforms, and income streams.

Career Pivot Playbooks is a weekly series curated by Katharine Gallagher documenting how professionals build resilient, future-ready careers by turning existing skills into income, often combining Substack with consulting, teaching, research, creative work, or business ownership.

The focus isn’t outcomes.
It’s about how careers are shaped in practice.

Gail K. is the creator of The Old Black Lady Chronicles, a newsletter for women over 50 with nearly 6,000 subscribers, and a business and money coach with 16 years of experience as an accountant before that.

She left a stable law firm career in 2021, rebuilt as a coach, then rebuilt again on Substack in 2025, turning one note about reinvention into 922 new subscribers in a single month.

She now teaches women over 50 how to grow a Substack, claim their authority, and turn what they already know into a sellable offer through her popular Grow It coaching lab.

You can follow her work here →

I've been a coach for the past five years. I quit my corporate job in 2021 and became a business and money coach.

Before that, for 16 years, I was an accountant working with a law firm in Washington, D.C. But even before that, I'd already owned a few small businesses. I owned a Molly Maid franchise, that's international, with an office, five cars, and twelve employees… so I have a lot of real business experience.

My ex-husband also had a business, a multi-million dollar government contracting business, and I taught him how to do the accounting for it. So by the time I left that law firm, I already knew how to run a business. I just didn't know yet that it would end up being mine, online, on Substack.

Honestly, I wanted to leave for 15 of the 16 years I was there. But I’d just gone through a divorce, my daughter was a teenager, and I needed something stable, so I kept telling myself, you can’t leave, this is a good job.

About a year and a half before I actually left, I started listening to The Life Coach School Podcast, and it started changing my mindset. I decided I wanted to get certified through that same school, but it was $18,000, and I kept telling myself, you’re going to retire soon, you can’t spend that kind of money.

Then two things happened. The head partner of the firm asked me to process the year’s bonuses and raises, I did payroll too. When I looked at my own, I had a zero raise and a $1,000 bonus, when I’d normally get five or six thousand. Nobody said a word to me about it. The next day he called me into his office and told me the partners had decided I was “highly compensated enough” and they weren’t willing to pay me any more money. I told him I probably wouldn’t continue somewhere I had no opportunity to make more, and I went back to my office and sat down… and I just heard this voice, I call it God’s spirit, and it said, they do not get to dictate how much money you make.

Not long after, I got on a call with my own coach and told her what happened, and she asked me, what if your business is your retirement plan? That was it. I took money out of my retirement account to pay for the coach certification, in 2020, during COVID, and on May 21st, 2021, I left the job to start my business full time.

So many things. I was an accountant, and I'd already owned a business before that even, so starting my coaching business as a business and money coach, my experience lent itself directly to it. I used to joke that I count rich people's money as I wrote checks for millions of dollars to the partners at that firm.

Most coaches don't have that kind of experience with big numbers, so when it came to coaching people on money, it felt very similar to what I'd already been doing… except now I was the one in charge.

My first clients didn’t come from my network at all. Right before my coach certification, I took a three-month program called Made to Do This with Kathy Heller. I was the star student, I was implementing everything. After the cohort ended, her team asked to interview me on a live about people who’d been successful in the program. I didn’t think much of it, but she ended up editing the other woman out of that interview and running mine on her podcast for Black History Month. I had no idea but she started telling her audience how great I was, and that’s really how I got my first clients.

Substack came much later, in February of 2025. That promotion had stopped a couple of years earlier and business had slowed down. I was on Facebook and Instagram but around that time it started getting ugly and political, and it just didn’t feel good anymore.

An author I followed on Instagram started releasing her new book in chapters on Substack, so I subscribed to read it, I hadn’t even heard of Substack before that. Once I was on there, I decided, you know what, I’ve always wanted to be a writer, I even majored in English for a while in college. I claimed the identity: I’m a coach, and I’m a writer and I went on Substack.

My audience is women over 50 who have lots of experience and wisdom and are ready for their next big thing. They've got the degree, they did all the things society told them to do, and now they're ready to do their own thing, they just don't know how.

In March, I created a Substack lab, which I'm rebranding now to Grow It. I'm building four courses out of it, but the one people really need is Grow It and Sell It. I teach people, mostly on Substack, how to figure out one simple problem they can solve, put together a tiny offer around it, and sell it for between $100 and $300. Since March I've taught 113 women through three cohorts of that group coaching program.

Harder than expected was being consistent, not so much with notes, but with the longer-form articles, and figuring out what should be paid versus free.

What's actually been easier, which most people struggle with, is figuring out how to make money. I don't really push paid subscriptions.

My thing is: have your own course, ebook, something that's your intellectual property, and sell that. Because I was already a coach, that part came more naturally. Even last May, when I got a wave of attention, I sold $16,000 worth of coaching off the back of it.

It was slow at first, the first three months, I felt like I was talking into a black hole, the way a lot of people describe feeling when nobody’s reading or liking their notes. I decided I wasn’t going to quit. Then in May last year, I wrote a short note about reinvention always being an option, and I got 922 subscribers that month. That’s when things started taking off.

My strategy, and what I teach now, is to treat Substack like you’re moving to a new city. You’re looking around for your favorite restaurants, your grocery store, the gas station, but you’re also building community and making new friends. Be curious, go out and meet people, comment on what interests you, be consistent, and don’t take it personally when it’s slow. It’s not personal.

Those first slow three months on Substack nearly made me quit. What kept me going was just deciding I wasn't going to… and it paid off, one note about reinvention changed everything within a few months.

Do it afraid. Don't believe what everybody else says, and don't even believe everything you're thinking, because our minds will lie to us, our brains are just trying to keep us safe. Step into your desire, be passionate about where you're going, keep your sights on it, and don't give up.

I always say, if you don't quit, you always win. You'll get to the destination. If you keep going, something is going to happen, you'll eventually build momentum.

I've been on Facebook for years and have around 14,000 followers there. I'm also on Instagram, and even though I don't post much, my Substack growth has started pulling people over there too, so it's growing on its own.

Now I'm going all in on LinkedIn, posting more and using a lot of the same strategies that have worked for me on Substack. Alongside all of that, there's the coaching business itself, and the ‘Grow It!’ Substack Lab, which is really the throughline connecting the writing, the coaching, and the teaching.

Quitting my job. It felt like jumping off a cliff, I was terrified, I got coaching, I went to therapy, I did all kinds of things to work through it. But that decision changed the trajectory of my entire life.

What's next is continuing to teach women how to build authority on Substack and turn what they know into something they can sell.

Connect with Gail K…

Gail K. - The Old Black Lady Chronicles: From a Law Firm Accountant to Helping Women Over 50 Make Their Next 20 Years Their Best Yet✨ The Career Pivot Playbooks Series

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