For years I’ve been wanting to build something of my own. Some form of online business with a creative passion at the core. A newsletter, a podcast, some coaching, maybe a product or two in the mix. And for years, I’ve had this nagging feeling that I’m doing it wrong. Everywhere I look, someone is telling me it should be simpler and faster. Post more. Build your audience. Make a course. Quit your job. Earn six figures.
I spent money for courses that led nowhere, wondering what I was doing wrong. Then I found Jessica Lackey’s book and the perfect name she’s given to this: the entrepreneurial casino.
Reading the book was a huge relief. Not because she makes it sound easy. If anything Jessica does the opposite by telling you clearly how much work is actually involved in building something resilient, how long it really takes, and why most of what you’ve been sold is nonsense.
It’s not a particularly sexy message.
The opposite of the casino is, well, work. Honest (and sometimes really hard) work over many years. And that’s exactly why it’s so important to know what you’re really in for so that you can navigate that path successfully without burning out.
I was lucky enough to get to chat with Jessica, and I’ve written up a few of my favourite highlights below. You can listen to the full conversation on YouTube, Spotify, Apple, or wherever you get your podcasts.
Highlights from our chat
1. Social media stopped being social when TikTok arrived
Before 2020, social media worked as a genuine discovery tool. It showed you content from friends of friends and helped you find your people. After TikTok, platforms shifted to passive and shorter, faster forms of content consumption. Posting every day hoping people will find you is now a poor networking strategy, and it’s exhausting. The people who built businesses solely from social media attention mostly did it in an era that no longer exists.
2. Use “Puppy dog internet theory”
Instead of posting into the void and putting all your energy competing for attention, find people you genuinely admire and… follow them around the internet. Like a puppy, not a stalker. What communities are the people you admire in? Who do they know? Go there, support those people, build genuine relationships. It sounds slow. It is. But it compounds in marvellous ways.
3. You might be building two businesses at once
There’s the short-term stuff you do to pay the bills and then the long term business — the thing you actually want to build and spend your time doing — that grows slowly in the background.
The short-term business is often about solving immediate problems for people. A job-job. It pays the bills while you build your network, sharpen your thinking, and let the longer-term thing compound in the background, without also demanding it immediately pay you.
4. Ask “what are you optimising for?”
If you need to replace a corporate salary within one year, the level of effort required is completely different from someone exploring a creative direction while their steady day job covers the bills. Neither is wrong, but being dishonest about which situation you’re in and what you want will only lead to misaligned decisions and burnout.
Regularly asking yourself what you are actually optimising for and answering that as honestly as you can is a very powerful practise.
5. Know your ceiling and if you actually want to break through it
Growing past a certain point changes a business fundamentally. More revenue means more infrastructure, more staff, more complexity. If you want to run a solo creative business providing a bespoke service on a one to one level, you have limiting factors built in. At some point that business model breaks if you try to scale it without changing anything.
It’s good to be aware of that and ask: if I grow this thing, how will it change? Do I actually want that or am I just pushing for growth because it’s the “logical next step”?
It’s okay to stop and live under the ceiling that makes you happy.
6. Do the stuff that sucks in order to do the stuff that sings
There’s the discomfort of “this is wrong” and the discomfort of “this is hard.” Succeeding means learning to tell them apart and accepting you’re going to have to do uncomfortable things to grow. Your first newsletters will be rough. Your first outreach emails will feel awkward. That’s the price of entry. Do it anyway. You’ll get better and used to it at the same time. Again, everything leads back to long-term compounding.
7. The opposite of scarcity isn’t abundance, it’s sufficiency
Ignoring metrics and “going with the vibes” whilst having zero clue what you’re aiming for is its own failure mode and often swings too hard in the opposite direction to the hustle bros.
There’s a minimum level of activity required to build momentum. In content, in networking, in outreach. Figure out the minimum you need to put in to make the kind of progress you actually want to make, shoot for that, and adjust as you go. Put another way, target your zone of enoughness and actually measure for it.
8. Seeds → Roots → Sprouts → Fruits
Plant seeds (relationships, content), build roots (infrastructure, systems, long-form thinking), track sprouts (early signals — something lands, someone shares it), then harvest fruits (clients, revenue, real results). Most people only look for the fruits and get discouraged before the rest has had time to grow.
9. Signal and momentum are not the same thing
A post going viral, an article spreading, a concept resonating - that’s all signal. It tells you you’re onto something. In todays attention economy, one positive signal does not mean you have momentum.
Momentum takes time and requires seeding the idea across different networks. It also depends on enough people encountering you enough times to actually notice. (Case in point: I only bought Jessica’s book the third or fourth time I saw it in my socials!) Don’t expect an early hit to be an instant flywheel.
10. Niche down, but let the pattern emerge
You can’t pick a niche before you know what the pattern is. Pick a direction, a type of problem, an area where conventional advice seems to be failing, and pay attention to what people reflect back. The niche emerges from the exploration. You also probably won’t have the language of your brand when you start. That develops with time too.
11. Don’t force your art to pay the bills
One of Jessica’s colleagues ran a podcast studio for five years while developing a show on a completely different topic on the side. The studio paid the bills. The show became the business with time. But she never forced the creative work to carry the weight it wasn’t ready to carry. Putting immediate financial pressure on the creative thing you’re passionate about is a good way to ruin it.
Resources
Jessica Lackey’s podcast: Aggressively Human
Book recommendations from Jessica:
Tiny Experiments by Anne-Laure Le Cunff
The Business of Expertise by David C. Baker (and the 2Bobs podcast with David C. Baker and Blair Enns)
