A Week In The Life Of…

A Week In The Life Of…

I enjoy reading other people’s ‘week (or day) in the life of’ posts to get a glimpse into their routine, so I micro-blogged every day last week. No week is the same when building a business, but how did last week look as a one-woman, bootstrapped business?


Monday and Friday are my favourite days of the week. I’m excited about the week ahead. There are still a lot of unknowns at this stage in my business. Whilst that would scare some people, I see it as an exciting time.

This particular Monday was interesting as it began with a shot of champagne. This doesn’t normally happen, but one of the businesses in my co-working space secured money to launch their product.

I made an ‘Insured Via’ badge for our customers. This is a badge they can display on their site to show clients, potential clients and visitors they’re professionaly insured. To my surprise a customer immediately adopts it!

A proof of insurance badge

I had a call with From Scratch who is working on With Jack’s copy. The current site doesn’t convey the value With Jack provides freelancers or the problem we solve. Sabine is helping me hone my message (a piece of advice drilled into me from Ignite).

I also finished watching the last of the InsurtechCon videos on YouTube. I watched every one of them to get an idea for where the UK insurance industry is headed.

In the evening I attended Tech Masterclass at Glasgow University. Rachel Evatt, who sold her startup to Skyscanner, was speaking about creative courage. I get a lot of value out of these masterclasses and use them as an opportunity to ask questions and seek advice.


I have a few copies of Learn From Great Design in my arsenal, so decided to run a giveaway through With Jack. My thinking here was purely traffic-related. A quick win (or so I thought) to get more eyeballs on the site.

It took time to get the landing page right, but one of the Slack groups I’m in provided critique (thanks!). For the amount of effort I put into this, however, it was a total flop.

Today was also about budgeting. I sent From Scratch, my copywriter, an email with the budget for writing With Jack’s copy. Budgeting is hard at this stage. I’m bootstrapped, early stage and a one-woman band, but I’m also open and transparent about money with any of the freelancers I work with.

One of my customers has built a forecasting tool. We worked out a special deal for With Jack customers and added it to the growing list of benefits. Having this kind of collaborative relationship with my customers makes me happy.

Another sociable evening. A photography group I’m a part of has their ‘end of wedding season’ party tonight. We meet in a pub, drink a few rums and talk shop.


Gah. Today I woke up with sore throat and cold symptoms so I worked from home. I wasn’t as productive as I am in the office and mostly used today for research purposes. There’s a new direction I’m flirting with for Jack.

For someone who likes technology and design, I’m not sure why it took me up until now to sign up to Tide—a business current account packed with powerful tools. First impressions: Why have I been using my crappy, dinosaur bank for so long?

I sent some cold emails today. I haven’t had any success with this so far, but I only do it when I genuinely stumble upon a business I’d like to work with and think would be a good fit. It’s probably strange for them to receive an email saying, “I really like your work. Let me arrange insurance for you!”.

Tonight I was supposed to attend GAB, my favourite meet-up. Feeling sniffly I decided to stay indoors. Instead I worked on clarifying my message after listening to How to Tell People What You Do in 3 Easy Steps.


Out of the office today. I’m visiting my old high school in Dunoon! Since leaving school 14 years ago I haven’t given much thought to education. That was until a couple of weeks ago when I gave a talk at my old school.

It made me think how powerful it is to have a positive impact on even one student’s career or attitude. Today I’ve returned to judge the YPI final alongside ex-pupil Sam Coley. Sam now runs a startup TickX.

The winners of YPI!

Apparently my old school has a poor uptake of girls with computing, so I’d like to get involved in addressing that.


I’m currently going through the Ignite programme. Well, kind of. I didn’t get investment or fully onboarded, but I’m attending the monthly off-sites in exchange for creating content for them. Today I edited and uploaded my latest Ignite video, so I’ll be sharing this on my YouTube channel come Monday.

I’ve been working with Catch Media, another of With Jack’s customers. Catch Media is managing my Twitter and Facebook ads, so I sent them copy and assets. It’s scary delegating tasks (and spending the money), but it frees me up to focus on other things. Everybody keeps telling me I can’t do everything alone, so I’m taking their advice onboard.

The Learn From Great Design giveaway came to an end. What a flop. I have 10 copies and only 5 people entered—so they automatically win. What should I do with the 5 remaining copies?

I end Friday with a few boring tasks. Catching up on email, going over analytics, sending payments to suppliers.

Now it’s time for mulled wine at the Christmas market.

Mulled wine at the Christmas market
Ashley Baxter's Picture

About Ashley Baxter

Ashley is building With Jack, business insurance on a first name basis. She likes video games, photography, and her dog, Indie. Based in Glasgow, Scotland.

Glasgow, Scotland iamashley.co.uk