Lessons learned from failing to become a freelancer

August 13, 2018

I quit my full-time job with a dream of becoming a freelance marketer.

After 6 months of trying, I failed to get one client. Zero. As a typical ‘overachiever’ this hurt my ego!

I made mistakes which I’m sharing to dissolve the flowery image of freelancing that’s often portrayed.

In the startup and self-employed bubbles, the narrative of taking a risk to achieve a dream, and reaching it, is prevalent. Sometimes, however, stories just don’t pan out in reality as you imagine them to. And that’s okay :)

Here’s what I learned whilst failing to become a freelancer…..

The grass isn’t always greener

Many things were appealing about freelancing.

In my mind, freelance life was going to look like this...

⏰Freedom to structure the day beyond the constraints of fixed hours

🤑Ability to carve an income beyond the constraints of a fixed salary

🙆Work on lots of exciting projects with different clients

🏠Au revoir rush-hour tube, hello working from home

🚣Freedom to work abroad or go on a random 3-month trip

🚀Freedom to experiment with ideas

🙌No boss

Certainly, the above lifestyle is one led and loved by many freelancers, but this often takes a few years to build up to. There are lots of not-so-peachy sides to freelancing to consider!

Freelance Reality

😩Chances are, you’ll get shit money for AT LEAST the first year of freelancing

⏲You’ll probably work insane hours for the first few years


💁🏽It can be lonely AF

💸Co-working spaces in London (despite the networking opportunities) are bloody expensive and often not suitable for those starting out


🤓Lead generation is an ongoing job in itself, above actual client work

As the months of securing ZERO clients rolled on, I found an appreciation for the perks of full-time work that I often took for granted. By the end of the 6 months I totally missed working with a team. I missed working on collaborative projects and the comfort of a monthly salary.

Entrepreneurship/freelancing is often glamorized online and full-time work is painted as a prison sentence. But, given the right company, you can work how you want, even within the constraints of a permanent job. More and more companies are building cultures that encourage flexible working.

Where did I go wrong?

There are many things I did wrong that stopped me getting a client. My approach was to outreach to early-stage B2B startups that had established a product-market fit but had yet to invest in marketing.

My offering was to help them set-up their marketing function (with a focus on inbound and content marketing) on a freelance basis.

The above approach resulted in engaged responses, interviews, and some full-time job offers. But none wanted to take me on as a freelancer.

Why did this approach fail?

  1. I targeted a money-poor demographic 🙈; early-stage startups.

  2. I charged based on my old salary straight away and turned down potential work due to this. I should have taken work on for less initially as it could have opened doors down the line and it would have been excellent practice.

  3. I didn't offer a niche enough service. I offered general content marketing options, instead of a specific service like an email outreach creation service. Start small.

  4. Lack of portfolio. I had no examples of freelance work for clients. Just examples from my full-time job. Building a portfolio for a particular marketing niche should have been a priority, even if this meant free/cheap work.

  5. Didn’t pivot early enough from my initial approach as I didn’t ask for proper feedback.

What would I have done differently?

If I were to rewind I would have...

Worked for free (for a bit)

I would have worked cheaply or for free INITIALLY. This is a controversial point as typical freelance wisdom says ‘DON’T UNDERVALUE YOURSELF’. This is totally valid but I think it should be ‘don’t undervalue yourself once you’ve got two brilliant case studies’.  

I should have worked for free for wonderful companies for 2 months (e.g Monzo, Slack, Sanctus) and delivered exceptional work for them. This way I would have highly credible examples in my portfolio before then approaching other potential clients.

Spoken to my target audience more about their needs

I would have dug deeper than I did into the specific marketing needs of my target audience early on.

Offered one super niche service

I would have focused on offering ONE super niche content service.

Instead of offering to do a buffet of content strategy, social media, CRM set-up, guides, blog posts, distribution ETC, I would have offered solely a B2B case study service. Research showed there’s a huge need for case studies. They’re valuable assets to sales teams in B2B startups but a pain to write properly.

I began to carve out this service towards the end of my freelance journey, but realised I wanted to go back into full-time employment by this point!

If you happen to need a B2B case study though, I highly recommend checking out Case Study Buddy by Joel K; he is serving this niche well.

Other general learnings

Humility ❤️

Sometimes, things don’t go as you envision. First world problem..... but I’d been so used to ‘achieving goals’ in the realm of academia/career throughout my life, that my ego didn’t know what to do when I kept ‘failing’ for so many months.

Suddenly I felt acutely aware that many friends were settling down, buying their first home....whilst I was still living with my parents and had thrown my savings into the air to pursue a path that had led to a dead-end. I felt vulnerable saying to people ‘I still don’t have any clients’ month after month and felt embarrassed to say I was struggling.

Letting the ego dissipate has been very humbling.

Talk to people if you’re struggling with ‘failure’. You’re human and there’s more to you than your external success :).

So many entrepreneurial ventures fail and yet in the startup/freelance echo-chamber, 90% of stories shared are success stories. I recommend Rand Fishkin’s Lost & Founder for a more in-depth exploration of the reality of startup culture.

A big ‘backup’ fund is vital

I’d managed to save a pot of money over the last few years as I live with my parents. I would not have been fortunate enough to try this experiment without this runway of savings. I highly recommend if you try freelancing, that you have enough to sustain yourself frugally for at LEAST 6 months. (I know not everyone has the luxury of being in a position where they can live at home to save).

Try freelancing on the side before quitting your job

If you work full-time, it’s worth experimenting on weekends or evenings before you fully commit to freelancing. This way you can get a sense of what it’s like to work with a client and you’ll have a small portfolio to build upon when you quit your job. You may also realize it’s not for you! I didn’t do this but I wouldn’t skip this step again if I ever retry self-employment down the line.

Resilience is key/ ghosting is RIFE

One thing that surprised me is how common ‘ghosting’ is in the freelance world! To clarify, ‘ghosting’ (just as on Tinder...) is when you’re engaged in a lengthy conversation with someone, often for weeks, until they abruptly stop replying.

There were occasions where I would meet potential clients in person, multiple times over a few weeks, spend days writing proposals and reworking them to meet new specifications. Then…. radio silence. The first two times this happened, it was emotionally draining after getting my hopes up. I didn’t understand the lack of an honest 'thanks but no thanks' email after weeks of dialogue, but it’s part of the freelance parcel!

Learnings from ghosting:

A) Don’t waste days writing proposals.

B) Ghosting is common, it’s not personal. Tis’ the nature of the game, so move on swiftly.

C) Until you get a signed contract, KEEP DOING LEAD GEN ACTIVITIES. A handshake yes is not a yes.

The freelance community is awesome!

If you’re starting out as a freelancer (particularly in the field of marketing), I suggest following this inspiring mix of freelancers, entrepreneurs, and communities:

Francesco D’Alessio - King of productivity tips. Francesco kindly met me for a coffee when I was first contemplating the freelance leap and gave lots of advice! His YouTube channel will help you get on track with a daily productivity routine.

Asia Matos - Asia began her self-employed journey around the same time as me and managed to make $10k in 90 days; she's killing it.

Ross Simmonds - for B2B marketing tips and general wisdom.

Elise Dopson - for examples of what exceptional B2B copy looks like. She has a weekly Freelance Friday newsletter which often contains UK specific advice amidst lots of the US-centric content out there!

Cat - Honest insights and thoughts about freelancing. Also UK-based.

Freelancer Co-Working, Networking & Socialising Meetup Group - A monthly event for freelancers to chat and work together run by the lovely Adam Blades. Usually held at WeWork in Moorgate.

Freelance Heroes Facebook group - An active Facebook group of freelancers sharing tips.

Slack groups with lots of supportive freelance folk:  thinktank, OG, techlondon, Launch

Thanks for reading my freelance-failure ramblings! As of July, I’m now on the look-out for a permanent marketing role. If you're at a London-based company with a passionate team, big vision, and forward-thinking culture, I'd love to have a chat 🙂

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