The other day, like clockwork, a draft from Brian Plain arrived in my inbox.
Brian has been my client since early 2019, and for the six years since then, he has written two articles a month, which he posts on his blog and shares via an email list of over 300 people. In all that time, I don’t think he’s ever missed one.
If you’ve ever tried to maintain a blog or email newsletter or any sort of writing habit, you know how amazing this is. I work with clients all the time who struggle to write one article every six months, much less two a month. And as you’ll read below, he actually started sharing content regularly via an email list over 16 years ago.
So it occurred to me, when I saw that latest draft in my inbox, that Brian should be studied! Or at the very least, I should interview him about how he does it, why he does it, and how his writing practice supports his business.
Tell me your elevator pitch… Just kidding. But really, what do you do?
I have a financial planning and consulting practice. My role is to provide advice, accountability, and a holistic view of my clients’ financial picture. I focus on helping my clients live better both financially and emotionally.
I know we’ve been working together since early 2019 — but you’ve actually been writing newsletters even longer, right?
Yes, my first newsletter was over 16 years ago. The format and frequency have changed over time, but the impulse is and was the same. Back then, I noticed a big opportunity: financial planning and investment professionals weren’t really using the online universe to communicate at scale in an authentic way. At first, my writing was about client acquisition. I was still building recurring revenue, so I needed ways to connect at scale. Looking back now, I realize it was also my way of processing my thoughts.
What was your marketing approach before you started blogging?
I leaned on community-based marketing—a mindset I borrowed from my dad (who’s a CPA and financial planner). The idea is simple: if you show up for your community authentically, build trust, and expect nothing in return, good things tend to come back to you. That might look like volunteering, joining boards, or just showing up consistently in shared spaces. In my case, that even meant playing a lot of tennis—helping run the men’s league, getting involved locally. I wasn’t out there giving a sales pitch. Relationships grew organically from shared experiences.
I also focused heavily on building relationships with professional partners, i.e. people in adjacent fields. My mindset was always: What can I do to help you? That way of being is still foundational for me.
Why start a blog then? What was it about writing content that was appealing to you?
Over time, I realized I’m more introverted than I’d previously thought. I enjoy one-on-one conversations, but those take time and energy. Writing became a way to communicate in a similar fashion but in a one-to-many format. Sure, you lose some of the personalization, but you can still write vulnerably and honestly, and reach more people at once.
How do you come up with new ideas consistently?
I’ve gotten better at formulating them over time. Most good ideas don’t happen while I’m staring at a blank screen. They come when I’m out walking, observing, and not multitasking. I’ve gotten more intentional about taking walks without headphones—just time to think. When something comes to mind, I jot it down and revisit it later.
I’ve also let go of the pressure to be “right” or “helpful” in every piece. Sometimes you write something that feels like you nailed it but it gets no reaction. Other times, something casual really hits home. I’ve had to accept that unpredictability as part of the process. For me, it’s about letting go of what my writing is “supposed” to be, and creating space to process what I’m noticing in my life, the world, and my clients’ lives—and sharing that in a way that’s honest and useful.
What’s your writing process like?
It’s tied into my broader accountability structure. I set a goal each year—24 pieces of content—and check in weekly with my accountability coach. I write best in the morning, so I block time then. Often I’ll go for a walk, head to a coffee shop, and start with a “brain dump” draft. I don’t aim for a polished post right away—I just need something to work with. Then I either send it off to you for feedback and editing, or revisit it later with fresh eyes.
Environment matters too. Coffee shops help eliminate distractions. At home, I might start doing laundry or other “productive” procrastination. Going to a different space signals to my brain that it’s time to write.
What’s the hardest part of keeping this up for so long?
I don’t find it that hard anymore. It’s something I enjoy and it’s impactful for my business. But I do think people trip themselves up by overthinking it—worrying about being on post #3 out of 24 for the year, or getting stuck trying to write something “important.” It helps to think of writing as an experiment and not something you’re “supposed” to do. There are so many different ways to get your message out there — audio, video, etc. You have to choose what’s right for you.
What impact has blogging had on your business—and on you personally?
When I started, I was trying to figure out if I could bring my in-person conversations online in a way that still felt real. That was the unlock in working with you: yes, you can, but you have to do it more concisely than you would in person.
Professionally, it’s become a way to stay present with my clients, even when we’re not talking directly. I’ll often hear, “You wrote that one for me.” And I didn’t! But it turns out we’re all dealing with similar stuff. Writing gives people a sense that I’m here, paying attention, and available when they need me.
Personally, I now think of myself as a writer. Not professionally, necessarily—but writing has become a way of exploring my natural curiosity. I write just as much for myself as for others.
How do clients and prospects react to your writing?
It’s pretty common that people respond. Sometimes they’ll email back, or mention something months later. A client once referenced a post where I talked about Sour Patch Kids—and I realized, wow, they’re really reading these.
The most satisfying responses are simple: “Thanks, I really needed this one.” I don’t write for those dopamine hits, but I’m happy when people feel comfortable sharing that it resonated with them.
AI is changing how people write and consume content. Does that worry you?
Not really. I’ve never written for SEO. My business is intentionally small—I only need to be impactful for 40 to 50 people at a time. AI gives people more access to information, but they still need help making sense of it in their specific context.
If you’re just trying to be an information provider in your content, sure, that’s dead. But if you’re reflecting, exploring, and inviting others to think alongside you, that will still be relevant.
What advice would you give someone just starting out with content creation?
Treat it like an experiment, not a success or failure. Don’t worry about whether your first posts are good. If you don’t look back and cringe at early work, you’re probably doing it wrong.
Also, find a format that’s in alignment for you. Writing might not be the thing. Maybe it’s audio or video. There’s a difference between something that feels uncomfortable vs. “I hate this” and I’m banging my head against the wall.
How do new clients typically find you today? Where does your content fit in?
Most clients come from referrals—existing clients, business partners, or friends of friends. My content provides a way for them to “trust but verify” before they make initial contact. Prospects can see how I write and think before they reach out. When I ask how they found me, I can often tell if they’ve read my work. It helps establish trust before we’ve even talked.
It also helps me stay top-of-mind for past prospects or current clients. Even if they’re not ready now, the writing makes it easy for them to find their way back when the time is right.
Any final thoughts?
Everyone should have a great editor. You don’t have to do it all yourself. Maybe you need someone to ghostwrite, or maybe it works better if the writing comes from you directly. There’s no one right way.
For me, writing became a practice. I’ve tried video and didn’t love it. But now I also record audio versions of my posts—just another way to make the content more approachable. The experiment process is about unearthing what that unique way is for you and your business.