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Introducing: Free Coaching Curious sessions

Pamela J. Hobart
Pamela J. Hobart
4 min read
Introducing: Free Coaching Curious sessions

This post is for people who are interested in one-on-one philosophical life coaching OR who are interested in entrepreneurship stories/details.

Anyone else, feel free to browse my other writing or move on with your day 🤗

Backstory: The Paid Intro Session

I launched my philosophical life coaching practice in the spring of 2019 with just one offer: the “False Belief Fix-Up,” a paid intro session. It cost just $75 at the time, and I truly had no idea if I’d sell even one.

Well, the paid intro session actually took off! By the time the summer was out, I was selling them at a slow but reliable pace (via a truly tiny < 200 recipient email list, my random personal Twitter account, and a smattering of blog posts at

I’ve done well over 100 paid intro sessions by now, despite several price hikes, and they have mostly been pleasant, educational, and clearly worth it. Over half of paid intro session clients go on to purchase at least one more coaching session - a staggering conversion rate, so clearly something was going right in the self-selection process.

(Shoutout to Coach Pony for putting the idea of a paid intro session into my head initially).

Why It Worked

There’s a lot to like about the paid intro session. For one thing, you immediately avoid spending tons of time and, more importantly, energy on people who are not truly willing to spend any money on your services.

This is not just a practical & financial benefit. Skipping right to the best clientele is also a motivational and educational benefit in disguise. New coaches, even those with intensive formal coach trainings under their belt, can easily get sucked into a pit of random one-off intro calls that go nowhere. This feels terrible, and also provides low-quality information to learn from regarding which clients are a good fit for you and how to work with them effectively.

The expectations built into a one-time, modestly-priced session are relatively clear and reasonable: the client gets to identity one “false belief,” suboptimal practice, potential habit change, etc that you then go and work on later. I was almost always able to deliver satisfaction via the intro session, and the environment was relatively low-stress for both me and my intro session clients.

Last but not least, offering a paid intro session allowed me to skip right to “on the job training” - these paid intro calls, as I always emphasized, were substantive coaching calls and not “sales calls.” I was able to quickly determine that I had some aptitude and desire for coaching work.

Unfortunately, one newbie coach’s feature is another veteran coach’s bug…

What Broke

Upon reflection, by myself and with a mentor and coaching peers, it seems that the very sales process that created my initial success is now shooting me in the foot.

In fact, the paid intro session is not so much a sales process as a sales non-process. I’d deliberately avoided ever having sales conversations with people! Instead, I’d simply send them an email after the paid intro session with some links to pay & schedule again, no pressure! (My mentor refers to this as “leaving the client at the altar,” ouch).

This previous method relieved a lot of stress, as selling doesn’t come “naturally” to me. “Leaving the client at the altar” even sort of works - I’ve consistently had paying clients this whole time.

But I’m no longer satisfied with the results, and I’m ready to be more involved in helping people decide whether my flavor of philosophical life coaching is right for them. Leaving the ball in the client’s court seems like an easy answer to not liking selling and not wanting to pressure anyone, but it just leaves clients’ coaching questions and concerns about committing out of sight and out of mind without ever addressing (or even hearing and considering) them.

With a paid intro and little follow-up, some clients who would really benefit from coaching either never meet me or decide not to continue for bad reasons. And even the clients who do continue may not be on the same page as me regarding in what manner and for how long we will work together, or regarding what the expected methods and results should be.

Happily, these are largely fixable business problems. And so, without further ado…

Introducing: The Free Coaching Curious Conversation

Although there are pitfalls involved with doing tons of free calls, it’s the industry standard for a reason. If people are considering making a significant further commitment, they want to talk about it first - fair enough.

Plus, free calls don’t have to be all horrible and high-pressure and salesy. It’s within my power to connect with people authentically, to offer them services that are likely to help (iff they are indeed likely to help), and to gracefully take “no” for an answer.

If you are curious about philosophical life coaching and possibly prepared to make a commitment to it (time, energy, money), I invite you to book a free Coaching Curious convo here via my site.

We’ll get to know each other a bit and establish what problems you’re facing. I’ll let you know (honestly!) whether I might be positioned to help, based on the hundreds of hours of experience I’ve racked up with over one hundred clients in the past few years.

If work together seems like it’d be fruitful, I’ll make you an offer, and I can answer any questions you might have about how philosophical life coaching works.

Space is limited for these, but I am genuinely looking forward to meeting readers and prospective clients in a new way. Book Coaching Curious here.

P.S.: Async Mini Consults

I’d still like to be able to offer a small, paid interaction for readers out there who dig my style but who truly aren’t even interested in having ongoing, $ facetime with each other.

So I’m trying another small offering as a counterpart to the free Coaching Curious convo: an Async Mini Consult.

Side note - remember Coaching by Email? I’ve been experimenting with that for over two years, with mixed results. A good number of clients have flourished with email-based coaching, even choosing it for many months consecutively. But others find the emailing to be slow/stressful/ignorable.

The Async Mini Consult is basically everything that was good about Coaching by Email, but without the diminishing marginal returns of emailing back and forth for a whole month. You’ll write to me, I’ll write back, one and done and on with your life.

You can learn more about the Async Mini Consult here.

Pamela J. Hobart Twitter

Philosophical Life Coaching in Austin, TX. Also mother of 3, Miata driver, and DIY manicure aficionado.