Prioritizing The Critical Path (But Sacrificing The Signage to Get on it in The First Place)
Working 'in' the business at the expense of working 'on' it
People told me to start a side project before quitting my job to become an entrepreneur. I didn't listen. But sometimes I wish I had—particularly at times like now when I’m battling carpal tunnel and less productive than I would be without it.
It’s funny because like any venture in life, if we knew how hard it would be upfront, we might never take action. And where’s the fun in that, right?
Take my first overseas move, for example. I made a solo move to London in 2014 (that’s a whole other story about failure and redirection you can read here). But I vividly remember my Aussie friend-turned-roommate Erin’s mom telling us with an exasperated sigh “Girls, you don’t know how hard it’s going to be.” Her mom was an ex-pat herself—to Australia from Ireland—and she knew well the tribulations of building a life overseas.
Erin and I reassured her we’d be fine with a mix of excitement and ignorance about the knockbacks that would darken our doorsteps. Years later—having found our ways back to Canada and Australia, respectively—when Erin and I reminisce about our London lives, we’re in firm agreement we were better off not knowing every challenge we’d endure. Otherwise, we might not have made the move and that would’ve meant missing out on all the incredible parts too.

Nine years later, I now think of solopreneurship as a similar game. It’s best to go into it with a mix of optimism and the mindset that the tribulations that darken your doorstep will probably be worse and more frequent than you anticipate. But if that doesn’t deter you, then you can tackle each challenge as it comes. And hopefully, like my London gamble, your highest highs will heavily outweigh your lowest lows. In fact, you’ll look back with rose-tinted glasses.
Working on Your Business as well as in it
I had a choice to make in early March. When I realized the extent of my carpal tunnel and everyone echoed the same advice about how “rest is the only solution,” I knew I had to prioritize fast. So I drew a line in the sand (metaphorically speaking, since I’ve seen a lot more snow lately than sand).
My biggest priorities as of late have been testing, iterating, and scaling the Community of Practice I created for course creators to build and run their first cohort in twelve weeks or less—and continue scaling from there. But with an unwieldy dent in my productivity, I had to prioritize even more.
Prioritizing The ‘Critical Path’
Every course has a ‘critical path’ through which you help students achieve outcomes. Because despite most people boasting sales revenue and completion rates as course success metrics, the real success of a course is the extent to which students actually achieve what they set out to do by taking your course. (This is why I always go on about Backward Design and starting your course design with student outcomes in mind).
In my case, forging a ‘critical path’ meant students:
Ran their first cohort (or a cohort if they’ve done so before joining).
Felt good about their first cohort (meaning they were ‘right-sized’ challenged and felt supported by myself and the rest of the community from A to Z—whether it was refining their course concept or landing page, testing their workshops, avoiding pit-in-your-stomach stress, sleepless nights, and so on).
Set a date to run cohort two (or whatever their next cohort is).
Of the roughly 40 people I consider part of my “beta testers,” since I released the course on January 18th and started office hours a week later, five people (representing 12.5%) have run or are in the midst of running their first cohort. I know of a handful of others building and running theirs without joining office hours, and the rest have been passive.
At first, I perceived these stats as low and thus indicating major flaws in my community and async course offering. So I started reaching out to people I knew well to check in and it turned out they were content—apologetic even—about not being active in the community.
I was still feeling unsure though, so I planned to reach out to the rest of the passive members when I came across a LinkedIn post advising against it. Here’s a screenshot of the post with an accompanying graphic:

The more I reflected on my own experience with membership communities, the more I realized how accurate this ratio is. Many of us take great value from being part of communities that we aren’t necessarily active in. Because they act as troves of advice and information we call pull from as necessary. But we don’t want people hassling us to “speak up more” as if we’re in elementary school. So as a Community Manager for a Community of Practice, don’t fret about passive members so long as the top 10% is showing signs of vitality.
Sacrificing The Signage to The ‘Critical Path’
Overall, I’m thrilled with the quality of the courses that have emerged from my community and I know each teacher is going to be huge. So it’s cool to be cheering them on from the sidelines, knowing I’ll be able to look back on these early coaching sessions and recognize how far they’ve come. I’ll share some case studies profiling individual course creators over the coming weeks, so be sure to stay tuned.
Now, the downside to prioritizing the ‘critical path’ at the expense of marketing efforts is I was working in the business and not on it to draw in more course creators. And there were consequences to that. After having 12-15 new joiners each month since the pre-sale in December, March was a marked drop-off with a mere two new members. Brutal—especially when I originally anticipated a spike because I’d planned to make marketing a priority after relying on word of mouth.
But I can’t feign surprise that I didn’t magically draw in more people when I’ve been working exclusively within the walls of my community and other client projects. All I can do is push forward and make marketing (i.e., working on the business) a priority going forward.
My Challenge to You
Assess how much work you’re doing in your business versus on it. Are you happy with the ratio? If not, how can you redistribute your work to better achieve your long-term goals?
Remember, if you spend too much time in your business you won’t be able to sustain—let alone scale it—but conversely, if you spend too much time working on it and fall down on delivering the work, you’re equally doomed.
It’s a delicate dance but all we can do is keep trying to find the right rhythm. So hang in there if you’re struggling. Try different experiments and don’t be afraid to scrap anything that isn’t working. Sometimes a process of elimination is the easiest route to success.
Thanks for reading this week’s newsletter and have a wonderful week,
P.S. If you or someone you know is looking for guidance and support to build and run a cohort-based course, check out my Community of Practice/Course. We’d love to have you.
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Sending you healing vibes. They won't actually heal you, but you can know someone in California (other than Christin) is propping you up. ✋❤️
Great stuff Alexandra! I can completely relate to the starts and stops that come with working in and on the business.
From my past experience, usually this pattern keeps going until a couple of things "click." Then you scale up to the next level, and the cycle starts all over again. In and on until the next breakthrough.
I also like that bit on that distribution of people engaged with your course. It's funny, it's a topic I talk about often on social strategy (and the theme of my upcoming newsletter), but I somehow failed to see the connection to course attendees until you pointed it out the other week.