| published by | Tim Schilling |
|---|---|
| in blog | Better Simple |
| published date | 2026-05-12 |
| original entry | A self check-in on the mentorship business |
I’m three months into my mentorship business and I’m running into some growing pains already. Thankfully, these are all logistical and not a core aspect of mentorship. I’m up to seven clients now. My goal is to support 20-25 people, so if you’re interested, set up a meeting!
This post is meant to be a check-in of sorts with myself. Originally it was supposed to be short, but obviously it grew!
Out of 9 prospective client calls, I’ve been able to convert 7 of them to paying clients. Three of them I need to have another successful meeting with before I can send an actual bill, but I’m confident those relationships will continue, so I’m counting that as a win! I attribute this to my ability to connect with people, build an understanding of their challenges, and offer relevant experience / resources / guidance to help them move forward. Admittedly, I share a LOT of community resources with other people. It’s infrequently content I’ve created. I’m pleased with how this has developed and the trajectory of this progression. It bodes well for my plans for creating curated content paths for people to follow without having to meet with me.
Another major win for me is the wide range of client needs I’m supporting. I knew going into this that I wanted to be adaptable to what people want, and it seems I’ve been managing that. I’ve got a client who I’m acting as a tutor and tech lead for; I’ve got a few clients that we’re having in-depth discussions on technical topics with. Another is asking for me to do regular pair programming to be more efficient and effective. Another has a great job but wants to find their voice in the software engineering world, and another is looking to carve out their place in the technical domain.
It’s challenging and rewarding to be able to discuss these varied topics. What makes things even more interesting is that my clients are around the globe. They are from Africa, Asia, Europe, North America, and South America. In these cases, there’s a lot more pressure for me to recognize my own biases and assumptions. I need to ask questions about how things work in the culture they exist within.
There are many aspects to this question. The purpose here is to identify adversity that I’m ultimately happy to take on because it’s good for me. For example, some of my clients are rightfully wanting me to help them make a major career decision, such as whether to stick with software engineering or to stick with a stable job. The amount of short-term uncertainty in the software world today, especially for junior developers, creates a lot of pressure. Thankfully, everyone understands that I’m not here to make decisions for people, but rather to ask questions to help them determine their own path. Then make that path smoother!
The other major challenges are logistical in nature. Finding quality marketing/advertising channels and scheduling meetings.
My entire marketing plan has been around providing quality content that attracts people who want to improve and are in a situation that can support mentorship. What I’ve found is that these people also tend to be people who are looking for technical support and to learn more. I’ve adjusted my plans to consist of more involvement in these spaces. My involvement here needs to be slightly different from what it has been in the past. Rather than purely answering technical questions, I want to cultivate the community a bit more. If I can cause a few people each month to come back a few more times, I improve my chances of them discovering my content on my site and therefore add a lead. The other benefit is that I’m hopefully helping the Django community retain new members and smoothing the pathway for their self-improvement.
Side note, my blog post on LLM contributions to Django had about 25,000 views, mainly from Hacker News. From that, I had zero people navigate to my let’s meet page. When I wrote up my announcement for my business, I had about 300 views and ended up with two new clients. Clearly Hacker News should not be a goal (not that it was), and knowing your audience is a force multiplier for marketing.
The last aspect is around scheduling meetings. I’ve been using cal.com as a meeting time picker. It generally works great. When someone picks a time, I make it recurring based on their plan. In a vacuum, this works well. But when I go to a conference for a week, this makes things much more complicated. If a person is paying to meet with me each week of the month, what happens when I need to cancel one of those weeks? I’m landing on providing a discount for the invoice that month. It’s annoying enough to make me consider switching to a “pay X dollars for Y meetings with an expiration on when those meetings must occur by” mechanism. I don’t want to abandon the recurring meeting cadence because I find without that, people tend to let things slide. The purpose of our collaboration is to be disciplined and accountable, so recurring events are pretty much a must. Either way, this will be something I think about more and will likely tweak.
Thankfully, my frustrations with the business have been limited. When I use the term “frustration” here, I mean something that I’m unhappy to deal with that I would like removed because it feels forced upon me or isn’t helping anyone be better.
One area I’ve been frustrated with is around billing cadences. Because I want to give people the chance to go through the meetings and then decide if they would like to pay, things get a bit wonky with Stripe. What ends up happening is that I create a customer account and backdate an invoice that suggests it’s actually for the upcoming month’s meetings rather than for the meetings that already occurred. This really isn’t a problem right now, but in the future it absolutely will be confusing when a client decides to end the collaboration because they’ll have one more invoice to pay. I have been doing my best to communicate this early on with the first bill, then expect that when the time comes, I’ll need to re-explain and refer to the original email.
The other frustration is with wealth inequalities. I would like to work with people regardless of their geographic location and culture. I hate that because of the chances of where we were born, I simply may not be able to work with someone.
While not my goal, I find many people want to be more involved in open-source software or in creating content. We need diverse voices in those spaces, and I would like my clients to be helping in that quest. However, the realities of the world get in the way. Because I am selling my time and not content, the impact of implementing Purchasing Power Parity is extremely high. At the same time, it’s hard for me to allow a person to spend a third of their monthly wages to meet with me twice a month. I know I provide value, but that’s too high a bar to live up to!
I suspect a solution moving forward is to have a set of PPP slots every quarter. This would limit me from overextending myself in helping everyone but also allow me to continue to work with people in other parts of the globe.
I’d like to see at least one of my clients “graduate” in the next quarter. I think this will expose me to another area of my business and will present me with an opportunity to secure an actual client testimonial!
Furthermore, I expect to host regular events on the Django Discord server. I’m between debugging tutorials and exploring book exercises. Though knowing me, it’ll probably be both.
Lastly, I want to continue to create content for people on the site. The goal is to provide curated paths similar to Trey Hunner’s exercise paths on Python Morsels. I hope that this will be reusable content that everyone can benefit from, not just people who can meet with me.
If you have thoughts, comments, or questions, please let me know. You can set up a meeting with me, or find me on the Fediverse, Django Discord server or use email.