• Richard Gilbert-Cross

Freelance in 500 days - day 1 of 500

By Tuesday 1st August 2023 I will be a full-time freelance writer. I vision myself as my own manager, working from a laptop, five days a week. I am writing this blog to track my progress, also to hold myself accountable.

I want to be 100% remote, in my home office but importantly, being able to travel as I work.

I would like to fulfil my creative purpose.

Working hard, writing for companies and publications for my wage. This will free up time and freedom to make YouTube videos, as well as write short stories, two other passions of mine.

I was born with a creative gift - writing - which I am completely wasting working in admin and wage slave jobs. I will focus harder than I ever have in order to work for myself, using my writing as the product. This will allow me to explore my passion for travelling, whilst exploring and meeting new people too.

From today to the end of 2023 is 655 days, but that's not so punchy. 500 is far more of a challenge.

My partner and I go on holiday to Thailand every couple of years. I have a vision of one day doing that with the freedom to return when we wish. No need to worry about coming back to an expectant manager and angry members of the public. If we stay longer, we can rent a condo and work from there.

I have a vision of travelling to Dubai for a holiday my writing wage has paid for. We’re in a reasonable hotel - sod it, we’re in the big one: Atlantis, The Palm. I’ve just woken up in our hotel room, it’s a Wednesday. We go the gym, have a swim and breakfast. Later on, we’re going to the top of the Burj Khalifa. When I get back home - if we don’t extend the holiday - work will be switching on the laptop and writing. Creative jobs that I’ve picked myself, for clients with whom I have a respectable and flowing creative relationship.

So, what’s my life like right now? I’m 33 in a few months’ time. After failing university twice, I worked in hospitality for ten years. The first five years in pubs in affluent areas of London, the latter for a well-known cupcake company, you know the one. I joined at a really crucial part of my life. I’d just kicked a drinking habit with the help of my partner, whose trust and love and support changed my life.

I was a nervous wreck, having to work without chucking back pints, in a job where I felt like such an alien. Everybody seemed ‘normal’ and I’d been scarred by my experiences in the pub. I was even adapting to no longer being nocturnal - finishing work at 5pm instead of starting!

I was very shaky at the start. After three months, however, I was promoted to the role of supervisor. They didn’t have one, but clearly needed one, so I just visualised the role for myself. There and then, I just started acting like the supervisor. I turned up early, I offered to help out with reports and writing the rota. I set an example. After three months, I was offered the role itself. After quickly adapting, the next visualisation was for manager. However, the current manager had been in the role for ages, with no sign of going anywhere soon (five years later, she is still there!)

Then, there was an accident where I set the fire alarm off in Waterloo station, causing the station to be evacuated. I clung on to the job by the skin of my teeth. Due to this incident, I was banned from working in the station. I thought it was all over. I was transferred to Blackfriars, where there was a team of three, including me.

Working life was different here, far less intense. The manager was incredibly laid back but clearly didn’t have much interest in the role, although he was good. I started imagining what I would do as manager. How I would change things, how I would interact, etc. After five months, the manager announced he would be leaving to study at university. Suddenly, there was a vacancy. With my partner’s help, I meticulously prepared for the interview. I planned how I would hit the ground running, how I would look after our regular customers, how I would grow sales, form excellent relationships with station staff and suppliers. Then the news came - I’d got the role!

I’d gone from joining as a recently-sober nervous wreck, with no plan for life, to a manager - in eight months.

Adapting to the manager’s role had its own challenges. My anxiety skyrocketed. I was paranoid people would think me not up to the role. I got sketchy about employees talking about me, forming opinions of me. On the people side of things, I had some issues to work through. On the numbers-side, however, sales really improved. I made good on my promise. Sales grew, we started to form new regular customers, and station footfall really grew in that time as well, and I managed to make full opportunity of this.

I had a big plan for generating large quantities of extra business. I started informing customers word-of-mouth that we cater for events and can provide large quantities of cupcakes for parties/gatherings, at short notice. Over the counter, I said yes to absolutely everything. If somebody ordered 96 cupcakes and we only had 24, I would hop on the tube to the other side of London (to a struggling shop) and collect them. Every day I told the team: yes, yes, yes! We don’t say no to any incoming business.

We didn’t yet have Deliveroo, and the couriers we employed sometimes needed a few hours’ notice, so I started my own delivery service. Customers started phoning saying they needed cupcakes in the next hour. So I would take payment over the phone, then prepare them. I’d close the shop up for twenty minutes or so - risky - and jog over to their offices to deliver. Bank of America, Goldman Sachs, many other private law and investment firms. You name it, we delivered there. Even if it was freezing cold and far easier to stay in the station - with my many layers of thermals and cup of tea.

Things were going well. I was visualising our sales expanding. The focus of this wasn’t making money - it was providing a service and making people happy. The busiest days on the cart steadily grew from £1k to £2.5k. I did an office event down Old Bailey: 200 cupcakes, all purchased through the cart (on top of the days’ sales) and gone in ten minutes. I got obsessed with expanding the sales. I sniffed out every opportunity, without ever being forceful or pushy. That’s just not my style. I never propose things or situations to people, like a salesman. I far prefer to lay the ground work and then wait for the person or company to approach me on their own terms.

I discovered the value of being open to strangers. Magical people came and went. It was as though every person held an invisible treasure - invisible to them, but which they could share with others. I’d always visualised being a musician. One day, I was speaking to a new customer about the jazz music I had playing through the speakers. He asked me if I liked jazz and whether I could play any instruments. When I replied yes, he offered me the chance to be in his band. Nervous and awkward, I said I would think about it. The truth is, I had exaggerated my musical abilities in order to endear myself and didn’t want to be found out. I pocketed his business card - he was a senior executive for a powerhouse financial company - but didn’t pursue it.

One day, the big sale I’d always dreamed of arrived. 1,000 cupcakes, with a 10% discount, for £3,000. Our target that day was around £800 and I finished the day with, I think, £4.5k. Needless to say, senior management were shocked and delighted. I vividly remember breaking my cool persona with customers to remark, “The total is - and I cannot believe I’m saying this - £3,000, please”. Once I left, the new manager gave me a leaving present: the original receipt in a frame.

After a year or so, I started to feel the restrictions of having such a small cart at a small commuter station. It was getting far busier than usual due to an increase in trains, but I fancied trying to test myself on a much bigger stage.

As part of my development, I always said yes to either covering at different stores or visiting stores, to pick up ‘extras’. ‘Extras’ were stock the manager was trying to get rid of (everything was fresh, daily) as their sales hadn’t matched their expectations. There was a few periods where we were doing so well, I’d visit shops every day.

One day, the flagship store in Mayfair picked up the phone to say yes, we do have extras. We always have extras, come on down.

I arrived the shop and was super impressed. I’d just spent the coldest winter in the train station and here was a physical shop, with heating! Whilst I was there, I noticed a lot of bad habits in the staff. Over a cigarette, the manager told me she’d had enough of the place and was thinking of leaving. Once I left the building, I immediately texted my manager and said, “Wow, what a beautiful shop! You have to let me know if there’s ever a vacancy, I would love the opportunity to work there”.

He replied laughing, saying the manager had been there for eight years. Had she had been complaining about leaving again? She was always doing that. Nonplussed, I remained steadfast with my vision. One day, I received a text message from my manager, asking me to call him.

She was leaving the company. Sales were actually declining each year. Our shops typically had a healthy 3% growth every year. Mayfair’s was -3%. Ours was 10%. It was a very tough decision for the company to make, he said, she’d been there for so long. But did I want to interview?

I got the role and managed to grow Mayfair to bigger and better levels from my previous store. We had some completely ridiculous days of high sales. I found a colleague from another store who shared in my vision of being the most profitable shop in the company, with the absolute best customer service. We became obsessed with sales and the mantra ‘yes, yes, yes!’ Whenever we had an average sales day - or low, it sometimes happened - we’d be back the next day with a vengeance. For high sales days, particularly Valentine’s, I’d be up at 4.30/5am and psyche myself up, dreaming that we’d smash it, and we would.

I ran the shop like this for a couple of years. I started to wonder, what was my next, natural step? Although the idea scared me a little (okay, it scared me a lot) I started to vision myself as the manager of the biggest and best shop in the company - Selfridges.

That place to me held so much awe and mystery. Whenever I met somebody who worked there they had a glow about them, and I would quiz them endlessly about the shop. It became a vision of mine and the timing didn’t yet feel right, but I would dream of this for myself. Maybe after I’d been at Selfridges I would become an Area Manager and start to earn the money (£35k+) I’d never dared to dream of.

Then Coronavirus hit. The shop closed for the foreseeable future. Suddenly, I was doing Customer Services remotely for the company. Opportunities to delight customers - always my passion - shrunk dramatically and I had to deal with customers screaming at me every day.

I tried to empathise with them and felt genuinely very sad that I couldn’t provide the level of customer service I was used to. But this was a side gig - I wasn’t furloughed, despite working in retail - and I was grateful to be busy during this crisis, as well as help the company out. Also, too, it would dramatically improve my chances of retaining my job once everything returned to normal.

In the meantime, they were eager for me to return to retail. So, I was offered the chance to go to one of the busy shopping centres. The working attitude here was very lackadaisical, with people often turning up an hour late, completely unfussed. I threw myself into learning the new skills it offered, such as making milkshakes, and really worked on improving the team’s coffee-making skills. I spoke to customers and asked why they were so frustrated with the shop. Once I’d got the broad picture, I communicated to the team and tried to change this. As I could not convince the team to live and breath the job - some were only part-time - it was so important that I adapted myself. Rather than completely ridding the shop of all negative influences - like I did with Mayfair - I wanted to instead try to be a positive influence. I would meet the team at their level and share my experience wherever possible.

One day, we were just recovering from a very busy morning when I got a phone call from my manager. The Selfridges manager was pregnant and wasn’t sure if she was going to return - and they wanted me to be her maternity cover. Manager of Selfridges! I pondered how far I’d come. Just before my first role with this company, I’d been fired from a coffee shop for not being good enough. After eight months I’d secured two promotions. Now, four years later, I’d been offered the chance to manage a company’s most profitable site - and hardest to run - in Selfridges.

I threw myself into this latest opportunity. It was a big task but I did well. I formed decent relationships with the hard-to-impress senior management. I made sure every phone call was answered or followed up. And largely, I delegated. Every day I was in the locker room with the Louis Vuitton staff, the waiters from the champagne & oyster bar, the personal shoppers, as well as of course the food retail staff. And every day I pinched myself, thankful and grateful I was here.

One day, I received a phone call. Did I want the job full-time?

This was it! I’d visualised my way to the top!

However, Coronavirus had really shifted my perspective on my working situation. After being in hospitality for ten years, I was at a crossroads. When I joined the company, I fantasised about having a retail job with weekends and evenings off. There were only four sites in the company that offered this (about 15-20%)

When I moved to Blackfriars, and then Mayfair, my desire had become a reality. For 80% of the time I worked for the company, pre-Coronavirus, I worked just Mon-Fri, with the shops closed evenings and weekends.

No frantic Saturday morning phone calls, trying to find cover. No working a double on Sunday because it’s suddenly busy. I had Bank Holidays off. I went away, recharged my batteries.

Through remote working, I’d discovered it was possible to earn money without using my arms as labour, without having to leave my partner and physically travel somewhere.

She’d been working from home all this time. To do the Selfridges job properly I made myself work some evenings and weekends. The shopping centre was the most difficult time, every weekend was required.

I was faced with a choice. My dream retail job or an alternative life I didn’t dare to dream of.

Many years ago, I was accepted for a job interview at a Selfridges clothes shop. I was so terrified of failure, I didn’t even turn up.

Using this as inspiration, I went this time for the courageous choice - and said no.

I informed the company despite it being my dream retail job, I no longer had the passion for retail and was currently looking for other opportunities for remote working.

For the first time in my working life I’d been employed solely for my brain and customer-facing skills. It had awoken a passion in me. I adored speaking with customers - and here was the chance to do this without preparing risk assessments, cleaning windows, having my arm deep in a grease trap and dealing with last-minute staff absences.

After a couple of months, Mayfair reopened part time, and I spent the other hours doing some remote sales job for the company. We had to phone up lapsed customers and offer them a discount code. It was far too repetitive and before long I started to visualise huge sales opportunities. After a couple of months, I received an email asking if we could provide some last-minute brownies for a work treat.

Pretty soon after, I was making about £2k a month for the company. All from handing out discount codes! I drafted sales pitches, asking managers whether they’d thought of sending individual brownies, flowers or hampers out to their remote team as a treat. The sales started to grow and each time I secured business, my manager was flabbergasted.

Eventually, however, the thrill of a challenge dried up. I was itching to cut ties with my beloved shop, as I was by now just going through the motions. Sensing my heart was no longer in it, I made the company an ultimatum: offer me the remote sales job full-time or I would seek opportunities elsewhere. As they couldn’t offer this, I found a Customer Services role in another company a couple of weeks later and handed in my notice.

Which brings me to the present day. After eight months in the role I have already manifested what I wanted. I have my dream rota, the extra responsibilities I’d wanted to make happen. My customer quality evaluations have all been 90%+, by far the highest. But this dream vision of mine, that I have never dared to pursue, keeps forcing itself into my everyday life.

Eventually, I dropped the fear and listened to it.

It’s March 2022. By December 2023, I will be a freelance writer.

I will earn either the same or more than I do now, which is £22k plus bonus.

Let’s have a look at the assets I have to make this dream happen.

I have a phone and a laptop, which is great. I’m lucky to have a second-hand MacBook my partner got me for my birthday.

I have a background in writing, which looks good on paper. However, it’s time to be honest here. My experience for writing at NME, for example - I did like two short articles during a week’s work experience there. That’s it.

Despite having an okay history of writing for a couple of magazines, I have never been paid a single penny for writing. I’ve never had an article with more than, I think, ten shares on social media. Nobody has ever sent me feedback, I don’t even know whether my stuff’s good.

I have no contacts.

I don’t have a rich family with connections. My mum works in a shop in my hometown, my siblings work at the factory in my hometown and my dad doesn’t work.

As a writer, I’m a nobody. If I don’t take action, nobody except family will ever know I wrote anything.

So, I’m taking action.

I’ve signed up for five freelancer websites. My CV and cover letter are on there. 0 job offers so far.

I recently made a YouTube channel called ‘The Vegan Traveller’. There are two recent videos on there, with 0 views and 0 subscribers. Well, one has six and the latest has one. These are all me, watching the videos to check something.

So I’m starting my freelancer life with literally 0.

My aim is to earn £1 from my writing. Just £1. This is definitely the hardest part.

Once I’ve earned £1, maybe I can earn £500 from that client. Or earn £1 from 500 clients. The same with YouTube subscribers. 0 to 1 is harder than 1 to 100.

So I’m starting from the bottom. Here goes.

Freelance gigs I’ve applied for - 0

Freelance job offers - 0

YouTube views - 0

YouTube subscribers - 0


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DAY 11 of 500 - Wednesday 30th March 2022, 6.43am Note to self: improve the website. I couldn’t find many writer websites as examples but I did discover: carolinegibson.co.uk and richmondwalker.co.uk