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Business Update: Fall 2021

A mid-year update for summer/fall 2021: new stack, professional development, service changes ahead.

Pamela J. Hobart
Pamela J. Hobart
4 min read

This is basically an off-schedule overall business update. You can see my first and second updates here and here.

(For all you freelancers/entrepreneurs out there, I strongly suggest writing these even if you don’t publish them, it’s pretty amazing to be able to look back for comparison).

New Stack (and it wasn’t Shiny Object Syndrome)

Mostly, How I Spent My Summer Vacation was migrating my stack.

(Other than dealing with hand foot mouth and RSV and also traveling with the whole family to a funeral, that is).

Previously, I used:

  1. Squarespace (website)
  2. Wave (invoicing)
  3. Satori (scheduling)
  4. ConvertKit (email marketing)

Now, I use:

  1. Ghost (website)
  2. Keap aka Infusionsoft (marketing automation)
  3. Acuity aka Squarespace (scheduling)

For notes and writing, Notion + Ulysses - no change there. Happy to answer questions about any of these, just drop me a line.

Now, sometimes switching around like this is just “Shiny Object Syndrome” that detracts from the core activities of the business.

I did give this possibility serious consideration, but in the end decided these diversions were worth it for me.

I do often actually write (and find clients that way), but Squarespace had become cumbersome enough that it was inhibiting my posting (I had even written some stuff and never posted, eek).

Less than a year ago I’d gotten set up on my previous scheduling platform, it was ok but had limitations that created extra work for me and I still had to use a separate invoicing thing. I had paid for a full year, but decided to treat my last few months as a sunk cost and move on anyways.

On the one hand, it was overwhelming to move these systems simultaneously - I’d spend hours at a time just doing small odds and ends of checking my old links, recreating and tinkering with pages, etc. At other times, I’d spend hours doing the same things: Squarespace doesn’t export nicely, so I had to re-create 75+ blog posts manually. Definitely I broke some stuff, which is embarrassing.

On the other hand, some parts of this were easier to do at once - if I had moved schedulers and then needed to change all the links in Squarespace first, that would have been slow and demoralizing.

Plus, I was doing client work all through these migrations - not avoiding the real thing in order to do more fake wantrepreneur stuff. Big difference.

Now with everything almost completely up and running, I feel calmer and more motivated, as hoped. No regrets!

Some Stats

As a result of moving to Keap/Infusionsoft, I now have a really good handle on the past and present of my business. Some updated stats:

  • Lifetime clients: 119
  • Number of paid intro sessions: 87
  • Intro session conversion rate (bought more sessions after the paid intro): 53%
  • Client-months of email coaching: about 70
  • Email subscribers: 938
  • Email open rate: 52%

Considering that I started out working literally a couple of hours per week and am still only around half time, these are very satisfying to see.

Wins compound, even if they’re small (and especially if they’re small, when small is what’s genuinely possible)


I’ve fallen off the wagon at writing this spring/summer! For me, the bottleneck is never a shortage of ideas or “writer’s block.” Instead, I suffer from a simple lack of time.

Being busy with my clients (and children) is a perfectly good problem to have, but I know that growing my business further will certainly involving writing more (and better).

I am optimistic that my new stack will noticeably lower the barriers to more writing this fall. I feel better already here in Ghost, like I really have no excuses not to just write & publish the damn thing.

(Also, I’m about to agree to write a book someone solicited from me as a kind of quirky side project, not about life coaching/philosophy stuff directly - more on that later).

Professional Development

I’m done getting my foot in the door, I have a continuous stream of clients, I have a writing practice, I will keep tinkering with marketing forever.

Now I find my interest turning towards a learning phase: “professional development,” so to speak.

Being self-taught and on-the-job-trained is wonderful, but it’s time to move beyond those foundations. To that end, I am working on:

  1. Internal Family Systems for Coaches
  2. Acceptance & Commitment Therapy Intensive
  3. Existential Psychotherapy
  4. Making Sense of Counterwill

More writing on these topics very soon 👀

(Want to sponsor any of these? Basically, you reimburse me for the class and I’ll give you free coaching sessions effectively at a big discount, we’ll play around with the topic that I studied. Get in touch and let me know!)

What’s Next: Minimum Coaching Commitment vs. Monthly Membership

As I level up, both substantively as a philosopher-coach and as an entrepreneur, I’m going to be restructuring my services.

When I started out with my practice, I felt very nervous about my prices exceeding my value, and it was important to me that I charge low enough to keep people coming in the door - if you have clients, then you have a business, and it's just an optimization problem (whereas when your prices result in no clients, you're just dead in the water).

But it's time for me to set a minimum commitment for working together at big, complicated life issues. Clients who have active problems sometimes schedule once and then disappear and then later tell me they were just procrastinating/avoiding, or they book a 5-pack of sessions and leave many unused without announcing a deliberate break, hanging over all of our heads.

Although it’s unsettling to put a highest-ever price tag on my work, clients get way better results if we meet consistently at first. This will look like a philosophical life coaching “package,” I’ll announce it soon. After that initial commitment, clients will be free to pop in for a session or two as-needed, no problemo.

At the same time, I still believe in the value of light, occasional coaching for people without big thorny things on their plates right this minute. For that, I have my membership Reality Check monthly - one short call per month to keep you on track.

I’ll be making some changes to the membership soon and finally marketing it properly too :)

That's all for now - thanks for your support - intellectual, moral, spiritual, financial, and otherwise <3


Pamela J. Hobart Twitter

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