2024 was a poor year for With Jack. It's the most underwhelming 12 months since launching in 2016. Growth slowed and I saw an increase in churn.

I can correlate this to a few events. Being able to pinpoint why it underperformed takes some of the sting out of it, but it's not where I want to be and I feel motivated to change that.

A lacklustre 2024 boils down to:

1. A difficult year with my mum's health, culminating in us being told her cancer is terminal and she has months to live
2. My binder. I'm 5 years deep and tens of thousands of pounds into this
3. The economy. Things kind of suck for freelancers right now
4. Churn. In 2023 I gained lots of customers that haven't been the best fit. This year I'm paying for it

Events that killed my motivation

When we found out my mum's cancer had spread and couldn't be cured, I lost all desire to work. Even things that usually lift my mood haven't helped, like training for Scotland's Natural Strongest Woman in the new year.

I'm spending more time with my mum. Work has taken a back seat. This is the way it's meant to be and I know when I look back on this period I won't regret my decision. Even when I'm not physically with my mum, mentally I'm distracted and emotionally I'm drained. There isn't much left to give to With Jack.

Business is still ticking over. Quotes are being processed, claims are being filed, customer emails are being answered. I'm very much on top of things but I do not have the capacity to market, strategise, create content… all of the things I've done previously that have helped my business grow.

Because of this, 2024 has been a year of standing still.

It's not just the situation with my mum that's lead to a lack of motivation.

In 2019 we started the process for With Jack becoming a Lloyd's coverholder so that I could get a binding authority. A binder is where the insurer gives me permission to quote and bind policies on their behalf, meaning I can build the technology to handle onboarding for me instead of how we currently manage it.

Currently we manage onboarding with a lot of manual processes.

1. Customer submits details on our quote form
2. Quote is manually processed and emailed to customer
3. Customer submits answers to risk questions
4. Policy is manually bound and emailed to customer

It's not a ton of work on an individual basis, but it's problematic for a few reasons.

Freelancers generally shop for insurance outside of conventional office hours. We lose sales because I'm not working at 10PM on a Friday, or checking emails on a Sunday. I used to, but dancing dangerously close to burnout lead me to introducing boundaries.

It's simply not scalable. I want to 10x my business, and manually processing everything takes time away from doing tasks to market and grow.

Oh, and I'd love to take a holiday without my laptop.

One day I'll do a deep dive on the 5 years of working on my binder, but the way it's made me feel is drained and apathetic.

The bottom line is it's challenging to stay motivated on any project that takes years to come to fruition. Especially one that experiences prolonged periods of stagnation. This is where doubt sets in.

Is this ever going to happen?

Can I commit to another year of this?

Is this worth the time, energy and money I've invested?

We took a big step forward this month when my application was submitted to Lloyd's. I felt particularly motivated that day, so I do think the binder has played a massive role in how I feel about work.

I haven't completely lost my spark. Solving the problem of non-payment lights a fire. But the way this past year has played out, I've not been working on parts of the business I used to find enjoyment in, like speaking at events, networking, writing code, creating.

The freelance market

I spend a lot of time speaking to freelancers. I've heard first-hand that the market has been challenging this year.

We've lost customers to full-time employment because freelancing has become unsustainable. A quieter job market has lead to freelancers being even more cost sensitive and, well, we're not the cheapest.

Freelance communities echo this sentiment with comments like:

"This year has been a huge drought when it comes to clients."

"The benefits of a full-time job has done wonders for my mental health."

"I want to leave the field entirely."

I don't have any control over the market so it's not something I'm going to lose sleep over. With Jack has already survived Brexit, a pandemic, changes to IR35, VC-backed competitors and now a cost of living crisis.

Plus, there are many freelancers who are thriving.

A bad year for churn

Insurance churn is always going to be higher when compared to other models like SaaS.

I don't think we can be doing anything else to address churn. The products we sell are useful, we provide reliable support, and with the introduction of services like Timely customers have access to more help than ever.

Other than positioning ourselves as the cheapest (not gonna happen), I'm unsure what more I can do to convince people to stay.

But this year was particularly bad for people churning mid-way through their policy. When reviewing our data most of these customers had something in common.

Last year a VC-backed competitor closed. At the time I picked up lots of their customers and was feeling happy. Partly because we saw a spike in sign-ups, but also because many of these freelancers had been given little notice that their provider was going out of business. It felt good to help them.

They ultimately haven't been the best fit for us. The interactions I had at the time we onboarded them should have acted as a red flag because they sounded like this:

Freelancer: "Your price is £X higher than my existing policy. Is there anything you can do to lower the premium?"

Me: "That's a really low price that we wouldn't be able to match. It might be worth staying with them."

Freelancer: "I can't. They're going out of business."

The logic baffled me. They wanted me to match the price of a company that wasn't making enough money to stay in business? There's a reason we don't compete on price!

Once the initial scramble died down and these customers had time to shop around, many jumped ship. This lead to some ugly metrics for us. There were 7 weeks out of the year where we lost more customers than we gained with sign-ups.

There isn't much I can take away from this other than it highlighting something I already knew. We don't want every customer. Not all growth is good growth.

I'm getting better at politely steering people in a different direction if they aren't the right fit for us.

Some highlights

There aren't many accomplishments to reflect on from 2024, but one of the bright spots was participating in the Autumn cohort of Techscaler.

I'll dedicate an individual post to Techscaler, but the accelerator helped me:

• get out of my comfort zone with discovery calls
• drill down on my idea
• start building it

We also built a new platform users are onboarded to, complete with courses and community features. That's pretty big!

Part of the binder required us to build and demo a system that could do all of the things the insurer and Lloyd's need us to do. It's been a huge risk. Despite investing a lot of money into this, we're doing it with blind faith that the application will be approved.

There are many nights I've lay awake worrying about it.

2025 can only get better

We're at a strange place with my mum's health. We don't know how long we have together. Things are changing quickly.

Whilst I want to set some goals for the year ahead, the most important thing is being kind to myself as I work through this. It's not going to be a perfect start to the year.

Being more intentional

This year I didn't do much work on growing With Jack. I've rode the coat-tails of previous years' efforts and I'm lucky we were still able to grow a bit.

Now I want to be more intentional with my marketing. Admittedly I feel so overwhelmed with modern marketing. Is X worth using? It doesn't feel like it anymore. Should I gamble on Bluesky?

My plan is to pick two channels to commit to. For business I'm leaning towards LinkedIn and short-form reels. For personal I'm thinking Bluesky and this blog. (Hey, this seems like a good time to include a call-to-action for my newsletter.)

Beyond that I want to run lots of mini experiments and be more intentional with measuring results.

Launching my Techscaler product

I've built and launched products before, but I signed up to Techscaler for accountability. Now the accelerator has finished I have the beginnings of a product.

I will launch this in 2025.

Do something every day to move the needle

I mentioned riding the coat-tails of previous years' efforts. I may have gotten away with that in 2024, but I absolutely can't spend another year standing still. Every day I want the work I do to move the needle on making the company successful. That's it.