Interlocutor as a Service

Back in August 2019, I soft-launched "philosophical coaching and conversation by email" with nothing more than a blog post and a generic checkout page ($100/month). I mentioned the email experiment in my personal email newsletter (~100 subscribers at the time) and probably also on Twitter.

I got one signup immediately, and others trickled in. To date, I've sold 15 client-months of coaching by email with close to no deliberate marketing efforts. Not bad!

Even better, I've learned basically what I wanted to learn in the process: philosophical coaching & conversation via email is better than viable, but only for some clients.

This post is a recap of my coaching by email experiment and serves as the formal announcement of Interlocutor as a Service.

The Heresy of Email

Paul Graham's been writing again lately, and this post - "Novelty and Heresy" - stuck with me. He writes:

One common way for a good idea to be non-obvious is for it to be hidden in the shadow of some mistaken assumption that people are very attached to. But anything you discover from working on such an idea will tend to contradict the mistaken assumption that was concealing it. And you will thus get a lot of heat from people attached to the mistaken assumption...

Every cherished mistaken assumption has a dead zone of unexplored ideas around it. And the more preposterous the assumption, the bigger the dead zone it creates.

Graham was probably thinking more along the lines of like... startups. But this idea of heresies embedded in moats of unexplored possibility immediately felt applicable to my work here.

And so I've tried to figure out: What exactly is the heresy involved in providing coaching by email?

Therapists and therapist-adjacent providers (like coaches) are right to emphasize that the efficacy of their work is grounded in the client-therapist relationship. Indeed, this relationship seems at least as important as the specific methods deployed in sessions.

(What this says about the conspicuous lack of depth and unconditional positive regard in our ordinary social lives... well, I'll leave that as an exercise to the reader).

Various entrepreneurs attempt to reduce the friction in establishing and maintaining therapeutic relationships via technology - apps and video conferencing, for instance. Someone even tried selling life coaching from a bot, plus random meat-body life coaches who would sometimes text you back, for $16/week (but that appears to have tanked, RIP).

So you're allowed to believe that technology-mediated real-time conversation maintains the critical "human touch."

And you're also allowed to believe that bite-size, peppy, mantra-type "self-care" and coaching can be app-ified.

But you're not allowed to believe that money can motivate people to get to know each other primarily or exclusively over longish text exchanges of quasi-therapeutic value. It's simply too far outside the therapeutic Overton window.

As such, your ordinary therapist won't write you much by way of a response when you email (it's all risk and cost for no $reward).

And the therapists and coaches who will email with you seem shady as hell, tbh. They do not have anything interesting to say about why you should choose that instead of real-time coaching, which makes both their real-time and asynchronous offerings seem suspect.

I have found that, for the right philosophically-oriented and self-selected client base, coaching by email is absolutely viable. Interaction via email provides intellectual (and logistical) benefits to both parties to the transaction. Philosophical coaching and conversation is not just a cheap substitute for something else. It's a different thing.

By now, I've exchanged tens of thousands of words with fascinating individuals. They were strangers before, but money gets people more interested in meeting each other's needs (h/t Adam Smith).

Extroverted, conventionally-credentialed coaches (i.e. not me) have little to gain and tons to lose by some portion of their clients coming to realize that the ritual of synchronous communication is partially - or sometimes wholly - dispensable to the undertaking of ritualized conversation. Thus they work to maintain the heretical status of coaching by email.

For instance, maybe coaching by email can't really be "coactive" - to which I say, so what? That's just one of many diverse approaches to ritualized conversation (with related credentialing body and interest groups, of course).

If coaching is simply a socio-commercial practice that arises in response to prospective clients' needs, then the needs can drive innovation over and over again. Let a million coaches bloom.

Writing Supports a Philosophy-First Approach

To the extent that they're separable in the first place, I view the coachiest part of my work as an extension of the philosophical parts.

It would be odd to discover or decide a bunch of things about values in life without doing anything to put them into practice, after all. In any case, the philosophy is logically prior to the coachy stuff. Values are prior to goals, virtues are prior to choices, and so on.

When you're speaking with someone, it is painfully easy to lose the plot of the cognitive elements of the situation: assertions, assumptions, implications.

Instead, a verbal exchange tends towards the emotional aspects of the interaction: who's feeling what and why?

To be sure, I am very deeply concerned with the interrelationship between cognition and emotion. I write regularly about how to think about, and deal with, the strange predicament of being a thinking-feeling-thinking-about-feeling thing.

But if emotions cloud or hog the conversation, the judgment and planning can't get off the ground. Email helps to prevent this type of coaching derailment.

Should You Take Part in the Epistolary Tradition?

The refined and effective letter-writing traditions of our forefathers are a marvel to behold. Those people wrote letters because they had to, I guess. But man, could some of them write or what. And, at the end of the day, writing is just careful thinking.

Email gets a bad rap, because so much of it is junk and bullshit. But if you've ever enjoyed a running, substantive email exchange with a smart friend, then you can imagine what I'm offering on demand here.

You can benefit from a deliberate letter writing practice (as via my email service) if you:

Have one or more areas of interest in your life that you want to consider deliberately (your career path, relationship troubles, want to find friends, want to work on your personal weaknesses, etc)
Do not feel very self-conscious about committing your provisional thoughts to writing
Will experience excitement, not intimidation, at receiving substantive responses (even though sometimes I will ask tough questions)
Appreciate the kind of accountability a coach can provide (such as relevant "homework" and check-in to support habit change)
Are curious about coaching and could use a conversational outlet, but have basically zero chance of ever willingly hopping on the phone with a stranger.

Coaching By Email Is Not For Everyone

None of this is to say that coaching by email is perfect or necessarily better in every client situation, of course.

Depending on personality and preferences, some people may strongly recommend explaining a complicated situation face-to-face or over the phone.

For people who don't write substantively very often, self-consciousness about writing skills could prevent a client from committing her thoughts to writing readily.

Then there's good old procrastination. If you're super motivated to undertake the coaching relationship in writing, then you'll use it to procrastinate on something else. But if a client doesn't have much of a taste for introspection generally, is averse to committing provisional thoughts to writing, or just is too busy, then the coaching thread will tend to fall by the wayside.

Troubleshooting the Email Format

Even for the right clients, the email coaching format presents some challenges. First and foremost, the response lengths tend to bloat almost immediately. Here's a typical occurrence:

Client: fills out new client questionnaire
Pamela: writes back with 3 one-line questions about questionnaire answers
Client: writes 2 paragraphs about each of the 3 questions
Pamela: writes multifaceted responses on each of the 3 topics, including links for reading & practical suggestions

Hello, wall of text!

Then what happens for the client? A few extremely dedicated readers and writers aside, the thread becomes too complicated and weighty to get back into easily - procrastination, avoidance, and even mild shame over wasting time/money and inefficacy can easily ensue.

As such, lately I've been actively trying to keep my responses short. This creates a different problem: managing the history of the thread. It's all available to go through at will, but that's a bit cumbersome.

Some of my email clients and I are experimenting with the use of online organizational tools to track of the chunks of conversation and tasks at play in the coaching relationship (e.g. a kanban board).

If this sounds insane to you, you're not in my target market. If it sounds exciting, please continue...

Formally Introducing: Interlocutor as a Service

Without further ado, I present the formal launch of: Interlocutor as a Service (IAAS)

Investment: $200/month - you can sign up here

What you get:

The opportunity to reflect philosophically on issues pertaining directly to your life (this is the magic of ritualized conversation, my friends)
Standard "coaching" support, as becomes relevant: facilitated goal-setting, accountability check-ins, and troubleshooting.
Full record of the interactions that you can look back on whenever you like, forever.
Email me as much as you want, I will always respond within 2 business days.
No commitment beyond month-to-month.
Existing clients receive priority if/when they'd like to return for another month in the future.

I am raising the price for several converging reasons:

Sustainability: It takes me 20-30 minutes to write most of these response emails, so my experimental rate of $100/month comes out rather low per hour. Since most email clients are benefiting substantially from this service, it is mutually beneficial for me to find a way to offer it comfortably on an ongoing basis.
Attracting the right clients: If no one got very much out of coaching by email, I'd have to keep the price low to get anyone in the door. Instead, I've had the opposite problem - my client load is near capacity, and I don't want to work more hours per week at this time. Higher prices will allow me to manage the pace of new email clients without implementing a screening process. Screen yourselves!
Shifting the nature of the coaching engagement: You invest in something because you care about it, and also you care about it for having invested in it. Even for the right clients, a higher price will encourage them to do what they can to get more out of me in our time together. I'd rather halve the length of client's coaching engagements but have them feel intellectually energetic than lackadaisically correspond for many months on end.

Which Interlocutor?

Whether the conversation will happen via voice or in writing, client-interlocutor fit is crucial to your being able to conduct the kinds of conversation you'd like to have (even though we can't predict exactly where they'll go).

If you're feeling it, go ahead and sign up here .

If you want to figure out whether I'm the right interlocutor for you, browse my blog or drop me a line.

I'd be happy to tell you more about how we could approach your situation to move your thinking and your life forward.

But, whatever you do, don't try to interrupt me to say coaching by email can't be done when I'm already doing it. 🤷