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Jack Redley

3 Key Factors That Make (Me) A Happy Webflower: Security, Freedom & Fulfillment

May 22, 2024

I gotta be honest - I've been completely lost in my twenties.

Physically, I've been more lost than Wilson (see reference).

I have lived in 5 different countries since 20). It was fun but often bizarre and lonely. While I was living in Brasil, for example, I lived in a 25 person house which sometimes felt like I lived in brothel/refugee camp.

Career wise, it hasn't been much better. I've been fired 5 times and I've never stayed in a job for more than a year.

I've tried all sorts from hospitality work to the usual freelancer stuff to some weirder jobs like being a club photographer or stamping grapes barefooted on a Portuguese vineyard (hope no one drank that toenail that came off in the 2016 vintage x).

Anyway, before you think I'm about to tell you that I finally know what the fuck I'm doing and here is the secret to life, I'm not.

I'm currently a lodger living with a retired couple in their seventies who tell me off for leaving a light on over night. Last night, a homeless guy challenged me to a fight while I was walking back from five-a-side with my bike after I got a puncture. Not exactly someone you should take advice from.

But I do think I'm getting closer to at least working out what I don't want to do and how I want to live.

Certainly talking to almost 100 Webflowers has helped.

Here's my theory - I think I need security, freedom and fulfillment to feel balanced and content as a Webflower. If you're feeling out of balanced, I hope this rambly article helps.

Let's dig in to these three:


Security comes first and for good reason.

We need to pay the bills. Life is more expensive than you think. My dad always said there's no such thing as a free lunch. What he's saying is that it's impossible to get something for nothing and as much as I hate agreeing with my old man, damnit he's right.

Life's hard but it's more like trying to fight a tsunami wave with a jam jar if you haven't got your basics covered. Weird metaphor but basically, what I'm saying is that money doesn't protect you from life happening to you (family members dying suddenly, breakups out of nowhere, spilling coffee on your shirt before an interview) but it allows you to control the parts of life that you can (renting a flat, buying a nice birthday present for your friend, taking your parents out for a meal).

When I was a freelancer, I had a really unhealthy relationship with money. I used to think money was bad and wealthy people were bastards which is ironic considering my privileged upbringing and, frankly, ridiculously fortunate position in life. However, I've come to realise money is not inherently good or bad but how one chooses to use it is good or bad. Money is like a knife - you can use it to butter your toast or you can use it to stab someone. The knife isn't good or bad but your action with the knife is.

Anyway, I guess this is a rambly way of saying that since I didn't have a healthy relationship with money, I charged very little (or sometimes nothing) for client work and this, in combination with a complete lack of boundaries, nor business acumen or awareness of cash flow, meant I was completely broke.

As a result, I didn't have any financial security and so I was forced to take sometimes full or part-time jobs I didn't like in order to cover myself. My lack of discipline and flighty approach to life meant I never got a depth of skillset in anything in particular and as a result, I never earnt solid money.

I still don't earn solid money to be honest - I'm now doing sales for Macu Studio when I was doing marketing and before that, I was doing freelancing.

I guess I regret not developing a depth of skillset in anything in particular which would lead to a depth of financial security but anyway I am finally able to be more secure than I ever have in the past.


I think part of the reason why I quit/got fired from so many jobs is because I just thought "who cares?"

I normally quit if I kept my mouth shut or got fired for opening it and asking that question to managers.

Putting aside the meetings about meetings, lack of decisive decision making, arse-kissing to rise up pay grades etc. I just felt like what I was working on didn't really matter.

Like if I died tomorrow, would anyone care about the work I was doing?

And was the company I worked for adding anything meaningful to the world?

Or were we just there to log on at 9 and log off at 5pm and get paid?

Freelancing felt like the answer - I could decide the projects that I worked on, be decisive when it came to decision making and choose what I earnt. Or so I thought...

I quickly found freelancing was hard - I quit one boss to potentially have multiple and realised I was out of my depth trying to wear different hats from getting the work to on-boarding the client to doing the work to presenting to QA to handing off the work to doing it all again after a post-mortem. After doing an expensive mentorship program, I was even more confused. The mentor asked us all to choose a niche by industry and the more specific the better to later reveal during the program she didn't know what her niche was herself and actually got told what her niche was by her business coach years after setting up and running an agency.

This was where Webflail came in. I realised there wasn't one way to freelance successfully but clearly a variety of ways. I had learnt a lot from working at Crafted Studios (shoutout to Dexter Washington and Chris Loggins) but was keen to know more. A podcast turned out to be the perfect undercover way to ask intrusive questions to people that knew far more than I did so I pursued that and have done that for almost 2 years.

This has been my fulfilment pillar from life - I get so pumped seeing people get something from listening to the podcast.

I feel fulfilled and energised speaking to smart people each week and it's even started to make me a tiny bit of money too which is mental.

This has lead to working with Edgar Allan with their team in Argentina, meeting incredible people all over the world and speaking events. I was on stage at No Code UK recently (as a compère rather than speaking but great experience!) and I'm even going to San Francisco next week to interview Vlad which is mental! That all came from trying to get answers which others also wanted to know.

However, I've come to see my security coming from my job and not forcing security to come from Webflail. When I tried to make Webflail my primary earning source, the why behind Webflail became lost. I put less focus on writing the newsletter, making the podcast, writing articles and generally trying to help people like me and more focus on trying to earn money.

This didn't help anything and I actually think money comes generally when you provide a tonne of value so essentially, when you do something really well, money will follow shortly after (if you want it to).

As I did Webflail, I then got offered more roles in community and marketing rather than web design or development. This was cool but I lost the time and creative freedom to make stuff if I was only marketing and Webflailing.


Now, of course, you may argue that Webflaila and jobs in marketing are creatively free. Yes, I would agree but I've come to realise that I still want to design and develop websites - it is just magic taking an idea through different stages to something visual.

I deal with clients in my job so I want to do "permissionless re-designs," - this means making websites for free for someone of something that hasn't commissioned the work.

That's where Blunt Scissor Studio comes in.

Blunt Scissor Studio is the name of me and friends that hack through problems fast to make websites about and for particular environmental or social issues.

The ideal outcome for each website is to make a tiny dent in the environmental or social issue the website is about.

It might be specifically for a charity, company or small business that's doing good, or a particular topic eg. Plastic Free July!

If one person is aware and/or takes action about whatever the issue is that I'm trying to tackle, then great - I've done what I set out to achieve.

The first one is a design for Clement Knives.

Project to be released this Friday.

Oh, and I have arranged to have Friday's off work to explore these ideas. 4 day work week (Webflail mornings and evenings) and then Friday to focus on Blunt Scissor Studio, weekends to get outside and touch grass.

Plenty more to come from this series of projects from Blunt Scissor Studio but for now, excited to tell you guys so that I have social pressure to keep up momentum!


There is a danger trying to get fulfilment and freedom and security all from the same source. It puts tonnes of pressure on everything being in alignment for your job and I have found that's unrealistic. Just like your partner is not necessarily the perfect blend of being all of the qualities you want eg. someone that's funny, reliable, rebellious, adventurous, attractive, decisive, empathetic, humble etc etc. or should you put that pressure on your job being the sum of all your needs.

Why am I telling you this? Because it's given me a load of energy that I've been lacking recently realising I can compartmentalise my needs around my skillsets and interests. I'm not sure if it helps you but I hope it helps you too if you're feeling a little lost in the quagmire of life.

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