Cover image for Why I Gave Up Freelancing to Become an Employee 😱

Why I Gave Up Freelancing to Become an Employee 😱

jameesy profile image James Bedford ・4 min read

Following on from my article the other day where I went through the tactics I used for winning and keeping clients from my five years as a freelancer, I had a lot of questions about why I made the choice to go back to a full-time career.

I wanted to take this opportunity to dive into that subject a bit deeper and leave my thoughts and opinions on the topic.

Please note - this article isn't me telling you that one career path is better than the other, this is what is right for me.

First We Need to Go Back In Time 🦕

My first experience of building something and selling it was actually when I was pretty young. I sold my first website aged just 14, a simple WordPress build back in the day when it was a new technology and it wasn't so simple to get up and running.

I sold probably 10 / 15 websites over the space of a year, which was pretty awesome when I think back to it, so I always had the mindset that the internet was there and you could make money on it.

I didn't do particularly well in school and left at 16 to work for minimum wage as a software developer for a construction manufacturing company, building and maintaining their stock tracking application in house and working on some PCB production.

Over the years I changed jobs but always stayed in the construction industry. I was a labourer and a van driver to name a few things!

So at the age of 25, I decided to jack in the job I was doing at the time, a Project Manager (again, for a construction company) to start building websites for people and really diving deep into modern web development.

If you want to know more about my success' and the methods then check out my post here - https://dev.to/countrysidecoder/an-ex-freelancers-guide-to-getting-your-first-clients-18ao

But needless to say, it was hard work. Very hard work.

Things I Liked About Freelancing ❤️

  • There was never a dull moment, I could be working on an e-commerce website one day and then an in-house CMS system the next. I got to know lots of people, lots of companies and I liked that.

  • I could set my own rules, boundaries and time frames.

  • I could (eventually) pick and choose jobs I wanted to work on.

...and no matter how hard I think about it, that is really it. Those three points.

Things I Disliked About Freelancing 👎

  • The time I could spend learning new tech was drastically decreased - I did not want to experiment with new tech in case it went wrong and cost me money, and any downtime I had was usually spent trying to locate more work or chase up existing clients.

  • You have no set income so it is much more stressful than having a salary. People don't always pay on time and when you have bills to pay and food to put on the table that is hard.

  • You need to be primarily a people person and work on your sales skills and not just your development skills.

  • Handover from clients can be an absolute pain.

  • It can at times be extremely lonely when you are working by yourself. You have no team to learn from.


So... Why did I Go Back To Full-Time? 🙌

I don't like the negative connotations revolving around working for someone.

I think it stems from the Gary-Vee-esque mindset of success manifests itself as "being your own boss", and I certainly thought that at one point.

However, I don't agree with that, and I came to learn it over time.

I looked up at who I consider being the influential developers and engineers, and they all work for companies. They excel at their career and move up to Lead Developers, CTO's, Engineering Managers. They are not losing because they are not working for themselves... They are winning because they are doing what they do best FOR someone else.

To put it bluntly, when I was freelancing I felt as though my skillset decreased. I was becoming outdated, falling behind the times and not being able to excel at my strengths but having to spend my time working on my weaknesses.

I missed being part of a team and having comrades all working together. Sure I like my alone time most of the time, but having someone who has your back if the shit hits the fan is a nice feeling.

Also, and possibly the main reason, security. I now get paid a handsome salary each month whilst getting all the other benefits I was missing. Sure, freedom is a brilliant perk of working for yourself, so I was able to find a company where I could set my working hours, as long as the job is done. If I want to take two hours for lunch to go into town and grab something I CAN. If I want to finish early I CAN.

I am infinitely happier and a stronger individual now for it.

Like I said at the start of this article, I am not trying to sway you one way or the other, but these are my personal thoughts and experiences.

If you have any questions regarding freelancing or careers then please feel free to leave a comment or hit me up and I will do my best to answer.

Also, go check out Chris Achards awesome post on how to start freelancing! - https://dev.to/chrisachard/how-to-quit-your-job-and-start-freelancing-as-a-software-developer-2ffh

Posted on by:

jameesy profile

James Bedford


Engineering Manager @ Monzo - Previously Front-End Lead @ Mango


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I'm a freelancer now, and I find it hard to swallow when you say your skillset decreased while freelancing!? So I worked at Apple and Google, as well has a half dozen dev agencies and tech was mostly fixed. Moreover project managers and product managers want something done asap, experimenting with new tech is a non option. Now, my experience as a freelancer-if I want to wake up and build an app in Golang and the next week in Python, or change my mind the next day and use Elixir, I say so, and nobody tells me I can't experiment. I'd say this is the best part about freelancing, my skill building now have no boundaries. And the client-if they have a problem with that then screw that contract! I sleep good at night.


I'm just telling my truth here David, this is what I PERSONALLY felt, I'm not speaking on anyone elses behalf :)

That's awesome you have found your balance now, and you are in a good place. However, my experiences have been completely reversed to yours!

It's so interesting to me how people experience different things :)

I get what you are saying about PM/PO's, however where I am they are fairly removed from any of the technical decisions. Our main product stack is Node, and we have grounds on microprojects and open-source work to experiment with what we want. It is encouraged even!

Your last sentence resonates with me where I think we may differ. See in that situation I would worry about it because I am anxious and cautious. Maybe I don't have the correct DNA to be a freelancer! But as an experience, I am glad I gave it a go for a chunk of my life, and I want to share my own findings with other people.


I'm working online self employed too atm and it has been great. But yes. There are different growth opportunities in bigger companies for sure. And the loneliness is a big issue! For most of freelancers I meet.

Good article!

Thanks!! There are definitely pros and cons for both


Freelancing can be a pain sometimes, the loneliness is real. Although for me after freelancing for 4 years, I felt I couldn't really scale my income based on limited time in a day, plus I have to do everything by myself - So I started my own agency and hired people to assist me. This was the balance I needed. I still code on a daily basis but only on projects I'm passionate about.


That is definitely a dream for many people. I think that if I was going to give it a go again it would definitely be with the intention of at some point employing people. That would probably alleviate most of the problems I was facing.

How long did it take you to get from solo-freelancer to having an agency? How was hiring people? Would love to hear more about your process.


I freelanced for about 4 years, last year august i got an office space. My first staff was actually a newbie, i had to teach him javascript, vue, he picked up nuxt.js and react by himself ( See our last project 2dotsproperties.com built with rails backend and nuxt frontend) . My second staff was a UI designer, he was great from the first day, although i still had to mentor him ( I was a sketch guy, he had only used XD we ended up switching to XD full-time).

Hiring people was hard man. I could only get newbies, so i had to train literately every one of my staffs by myself mostly during weekends we build side projects. Things has gotten smoother now, the old staffs trains the new guys.

That's really nice that you invested people who are now training people up though! I bet it has been so satisfying to see your staff grow in skillsets.


It seems like all the things you dislike about freelancing can easily be solved by doing two things: 1) finding jobs using a good freelancing platform and 2) working from a co-working space.

I'm working as a freelancer on Toptal and the platform eliminates almost all of the disadvantages you've mentioned. You don't have to chase new clients. You just set your hourly rate as well as the number of hours you're willing to spend working per week and internal recruiters reach out to you with the jobs that you're the best fit for. Toptal also guarantees that you're always paid on time regardless of whether or not Toptal has received payment from the client. And the bonus is, there's an internal Toptal Slack where freelancers share their ideas and help each other so you feel like you're part of a community.

When it comes to meeting people in person, there are Toptal community events all over the world. But you also need to find a good co-working space where they don't offer you just a table but organize events for the members. That way you'll get to know other people there and it would feel the same as having colleagues. I was lucky enough to find one (PaperHub) just around the corner from my apartment in Prague.


I'm looking into freelancing and I'm curious what you and other Toptal freelancers think about the recent news about the founder withholding equity from employees and investors. Does that have any bearing on your view of the company? It seems unethical to me, which is why I decided to not work with them but I would think people getting some large portion of their income from Toptal would be much more conflicted than someone just starting out.


I cannot speak for others but I also think it was unethical. Nevertheless, the world is not fair and they should have signed better contracts. Would you refuse to work for Facebook just because Mark Zuckerberg stole the idea, then tricked his co-founder and left him with a really small amount of stock options? (I mean ignoring Facebook's current problems...)

But this behavior of the Toptal founder got me thinking. It's never been a good idea to have all power in the hands of a single person. So I started to look for other options in order to have a back-up plan if something goes wrong. Although I still think Toptal is probably the best platform for freelancers.

Would you refuse to work for Facebook just because Mark Zuckerberg stole the idea, then tricked his co-founder and left him with a really small amount of stock options? (I mean ignoring Facebook's current problems...)


Good idea on the backup plan. I'm looking into Facet and Arc.dev (formerly CodeMentorX). So far it seems as though Facet is more personal and Arc.dev has more work, but it's really early days for me. If you know of others I should look at, let me know.

I would be interested to hear what your opinions were on any of these platforms Chris.

Just recently I've joined a new freelancing network based on really interesting concepts.

It's an open network owned by its founders, investors and freelancers themselves by issuing their own tokens. The network only takes 10% fee on top of your rate to cover its expenses and they want to give away all profit. The value of the network will be determined just by the token. They also want to hand it over to community so in the future freelancers will be resposible for vetting new applicants and they will be rewarded by the tokens.

This network was founded by a guy from San Francisco who has already sold two companies and his third one is heading towards IPO. He's also been an investor focusing on blockchain technologies and this is his first attempt to create a blockchain-based marketplace. He plans to open other marketplaces in different areas in the future.

There are not so many jobs available on the network at the moment so I wouldn't rely on it as the only source of income. But I think it has really promising future ahead. Right now, it's in private beta phase but you can register using my link: app.usebraintrust.com/r/tomas1/


Thanks for such a detailed reply.

Your right, things would have been made much easier for me if I had found a good platform to stick to. Toptal looks really good! Also, I know a lot of people who recommend co-working spaces. I'm glad that worked for you.

I just think I prefer being part of a team for a company. I am moving to a different job at the end of next month working on a product that I use daily and love and the excitement I have to be allowed to work on such a product far exceeds any passion I had whilst freelancing.


I'm glad you've found what you were looking for. I can see comments from other people who followed the same path as you did and finally ended up as an employee in a good company.

It's interesting to see how we're all different. I worked for two companies before and then co-founded another one. But freelancing fits me best so far. I always enjoyed first few months in a company and then it started to be boring. I probably need a constant change and that's what freelancing gives me. However, I'd like to give entrepreneurship another try in the future as I see it as the most fascinating career path.

I always enjoyed first few months in a company and then it started to be boring<-- I agree with this as well, but I'll usually feel bored about 2 years into the company. It's good to know I'm not alone on this.


This is great - I agree with all your pros and cons for sure. It's a hard balance to walk! I think there's also no problem with freelancing for awhile, then working for awhile, then jumping back to freelancing again, etc - the freedom is great for awhile, but like you say: it can also be extremely stressful.

Thanks for the post! This is great reading for anyone who wants to be a freelancer (or who thinks it will all be ponies and rainbows :) )


Thanks Chris! Just threw a link up at the bottom of the post to your latest article, I think that is really helpful for anyone looking to get started!

I also tell people there is no harm in working full-time and doing a little bit of work on the side to dip their toes in the water.

The lifestyle suits some people more than others, I just don't think it was for me, but I am ultimately glad I gave it a good go.


Yeah, great point about on the side - it's a good idea to see if you even like it or not.

And I just edited my post to include a link to yours as well :) I think they're a great pair of articles, coming from both sides!


I somewhat agree with you but skillset does not suffer in freelancing but what suffers most is dealing with people for money. Its called recovery and it is one of the hardest things in the world. As an intellectual, i think this recovery is a wasting process for anyones intellect. People are just so stubborn on paying for the work you have done as a freelancer.


Yeah, I agree with you.

My points were based on the fact that I thought my skillset took a battering, however, I know many freelancers who continue to flourish in strength whilst working for themselves... It just wasn't right for me :)


It wasn't right for me too!... I am beginning to find more happiness in the job culture. I guess. We need peace and we deserve it.

Yes :) As I have gotten older, I have learnt that life is less about impressing people and doing what makes us happy as individuals. If I want to work a career because that's what makes me happy then I don't really care if others consider that an easy way out :) It works for me


I have the feeling, most of the problems you had with freelancing are solved by simply charging more.

If you make much more money than you spend, you have all the time to experiment, you can wait through a dry spell and late paying customers.


Oh no, please don't get me wrong! I did not want for money at all, I actually ended up really comfortable. However, I am quite an anxious person by nature, and even though I was pretty secure, it was always on the back of my mind that it just wasn't a finite resource.


I think your approach to freelancing was completely wrong.

I started freelancing as a web developer with the primary aim of building my own agency. The objective was to recreate the type of working environment that I would thrive in.

12 years later I have built a web design agency, Teamalfy.com that has 5 permanent staff and 3 contractors working from my home office. I love my team and I am never lonely.

I can never look back or go to the corporate world and chain myself to a desk. Never!


Thanks for sharing :)

I never set off with the intention of growing an agency, maybe I should have done?

I would love to learn more about your process of growing your agency though! What were the hardest parts and the best parts?

Awesome website by the way!


Even if you’ve done everything right you can still fail at freelancing. I’m not sure why you are giving him a hard time because he doesn’t want to freelance anymore. Also, clients can choose to stop working with you at a drop of a dime. You can still feel chained to your computer screen at the mercy of your clients with freelancing. I think both have their pros and cons, you just have to do what’s best for you.


Sorry mate but sounds like you've either had seriously crap contracts or a very Bad CV. I've been freelancing in IT 20 years and every contract rolling... like almost every other IT contractor I know.


No need to apologise :)

I think we have our wires crossed here. By "freelancing" I am not talking about contracting, although they have fairly narrow lines, I mainly made my career from approaching companies and saying "do you want a website?".

I have worked as a contractor as well and it has been a good experience because I have the certainty of income and also most of the time have been embedded within a team that already exists.


Not always true and you don’t need a CV for freelance work (that’s for full-time employment), you need a portfolio. Lol!


I can sympathise. I was an employee for years and then went contracting (I'm UK based like you so I guess you know what I mean by contracting rather than true freelancing - longer term projects in clients offices). I did that for 5 years and I did enjoy the projects and I learned a lot as of course I was embedded in teams, both filled with employees and in come cases all contractors. But eventually at the end of last year, just after buying my first house (my wife and I are a bit older than most first time buyers and we jumped a rung or two by stretching ourselves), my contract was cancelled with one weeks notice at Christmas. It was a remote contract which is great as we live in rural Devon with meetings in London every couple of weeks. But suddenly I was in a precarious position with a big mortgage and no work available locally. I didn't want to work away from home as both my wife and I find it very stressful but I felt it was my only option. Out of the blue, a permanent home based job came up that both paid well (all the permanent local jobs are pretty under paid round here), and offered the chance to get into whatever I wanted to a degree: the company uses C#, Java, JavaScript/Typescript, Kubernetes etc and everything is now in Azure and there was the freedom to use whatever we needed in Azure so long as we could justify it. Funding for conferences. Time to learn and then present in brown bags. The option to work out of an office or at home, and no need to go to any office more than once every few months or so if you want (ideal when you live in Devon!).

I applied, went through a multi stage process inside a couple of weeks and started less than a month after initial contact. And it's brilliant. I have security, which took away the gnawing anxiety and growing depression, I work with a team of brilliant developers based all over the UK and Europe, we all get to pitch in on reviewing applicants and interviewing so you have a say in how the team grows. The benefits are good. And best of all, no more worrying about how you're going to win business to pay the bills. I can concentrate on learning and improving myself and helping others as well.

I personally was a reluctant contractor. It was a circumstance thing and I never really enjoyed the stress of renewal time or trying to get new contracts or the hassle of paying the right taxes at the right time (even with an accountants services). So I completely empathise with your viewpoint.

Of course everyone's mileage will vary, and that's fine. But freelancing and contracting are not for everybody, although I would urge anyone to at least try it. I was fortunate to find a good permanent job at the right time that pays what developers are actually worth, bit I also think that in too many places developers are undervalued and underpaid still, which is a problem.


Thanks so much for sharing your story :)

As you touch upon, I would consider freelancing and contracting slightly different things. I have always had fairly good experience with contracting, but again, always suffer with anxiety when it comes to renewing. It's not like it is an urgent threat most of the time, however, I suffer with anxiety pretty bad anyways, and I worry about things that don't necessarily need to be worried about! It sounds like you have found the ideal place though!

Me and my partner are currently Berkshire based but are looking to move down to Devon somewhen. I have been doing my research and you are right with the fact that many jobs that way are underpaid, however, the cost of living is substantially lower. My dream is to be employed fully remote for a London company, which allows us to up sticks and move down south and benefit from the lower living costs whilst still taking a city salary. It sounds like you have managed to sort out a similar arrangement :) that is awesome! Devon is a beautiful part of the country.


I know the area you're in fairly well - I was born in Wokingham and grew up for 10 years or so in Crowthorne, and my Dad retired to just outside Basingstoke. Devon is fantastic and your goal is definitely achievable: My offices are London and Shrewsbury and I have to go every few months at most. But I know a guy who is a dev manager (might even be more senior now) who lives near Barnstaple on a smallholding and goes to London every so often as well, so it's very do-able. My employer actually has a blog post on Medium on our interview process and how to apply to us (it's a code test) and they actually encourage people to apply speculatively, although they also have vacancies page but they do like to hear from good devs no matter what. I think that sort of attitude is slowly becoming more prevalent, which I believe is a good thing.

Don't be fooled by the cost of living thing: It can be cheaper but not everywhere. I'm in East DEvon and prices here for houses etc can be pretty steep. Of course, it will likely still be cheaper on average than in Berkshire, but you often have to use the car more and so on. Of course, if you want sea views then double the price for the same hou8se anywhere else, and if it's Dartmouth or Salcombe, then triple it :)

I'd definitely encourage you to follow that dream though: My wife an I love it here and are so glad we made the move. It's the quality of life as much as anything. Who knows, maybe there will be enough of us to start a home workers industry group for meet-ups and conferences and the like!

Oh yes, we are pretty much 20/30 minutes outside of Basingstoke :) Small world.

Yeah for sure, the quality of life is much different. Its good to hear from you first hand that you have made it work and know of other people who have done the same.

Hopefully, I'm making strides to allow that to happen as I plan on having a new job by the end of this year 🤞🏻


I really like the honesty and perspective. I also freelanced for about 2years albeit not that successfully. I felt my skills didn't really grow and had some issues when applying for full-time roles. I just didn't get the big picture of working with large complex teams.

It is also true that my skills didn't grow as significantly as it could have. I was not an expert at anything. Today I would be working on legacy JQuery code, tomorrow Vue, then a client throws in React. One time I had to use FetaherJS with a 24hr notice, then I never touched it again. The bright side it enhances my ability to learn and adapt to technologies as fast as they come.


For sure :) We always have to find positives and a bright side of any situation!


I really appreciated your honesty for your reasons to returning to full-time work for an employer. I was having a similar discussion recently. You brought out some points that overlooked (lack of new tech upskilling, missing team environment, etc). It truly comes down to what is best for the individual. Thank you for emphasizing that!

I look forward to when I can work for a flexible employer too :)


Your welcome!

For someone like me, a flexible employer is everything. It really gives the best of both worlds and I like the fact that I am trusted to just get on with the work because they have employed me to be an expert in my craft.


My wife took 5 years off while our children were young. While I've stayed corporate she has been taking on freelancing work that gives her plenty of time to pick-n-choose when and how much she works so that she can spend with the kids. Meanwhile the family stays covered with health insurance from my salaried jobs.


That definitely sounds like a good mix. My partner and I do something very similar, she was able to drop down to three days a week at work and she uses the other two to work on her own skills that she enjoys with the intention of earning a bit of side income.

I have it lucky that I am being paid full time to do a job I love. I would love for her to also spend most of her time doing something she enjoyed.


I think when you have large bag of experience in software (10-15 years) here is where you can go to freelance if you find hard to stick with employer. But at first in my opinion you can open your mouth and say to employer let's try something different and see an answer. Good employer will be always on your side if he cares and knows in long distance it will work for business also


Yeah I have always found employers are fairly lenient if your requirements change. If you are doing your job and doing it well they are going to want to keep you on :) Thanks for the post.


I have been freelancing for more than 10years and the experience has awesome. But I recently accepted a salary job because I felt the need to refresh my network by meeting new people and making new friends. I also want to have a little feel of how the professional environment runs these days so I can spice up my customers relation skills. Contrary to your experience, freelancing gives you a lot of opportunities to learn new skills and improve on old skills at your desired pace. But the real danger there is that you may not be a Master at anyone. This is because you're always going to expand your skills set and keep up with trends to attract new clients. I still freelance at my spare time but I will return to fulltime freelancing after one year in this job. I like the freedom to travel as I want and the freedom to attend conferences which I have lost at the moment.


Thanks for sharing your story, Michael.

I'm fairly lucky in the sense that my company promote and support your attendance for conferences. It's a really nice touch. I wish you all the best for when you go back to your freelancing career!


Hit the nail right on the head. Skillset decreasing, the feeling of being part of a team and security. These were also the same reasons why I went back to full time employment.

I felt that I was progressing more and was exposed to greater technologies in 1 year of full time employment, as compared to my 3 years of freelancing.


I think maybe because I was fairly early on in my career it might have been made worse, but still we web development evolves and changes so rapidly its good to be in a team that are constantly evolving with change.


Hi, so in my second year of university, I started freelancing because I wanted the experience of working on a real project and it went really well for the first 4 or 5 months I was making sites in basic HTML, CSS, PHP, SQL for local photographers or some portfolio sites, etc.

But after 4 months I felt like I am just doing the same thing again and again, Starting with HTML, CSS then writing similar CRUD functions in PHP and it just kind of stopped me from going into the core of anything. Every day I was just making plain websites. Also, the clients and the whole situation was making me anxious.

So after a year of freelancing, I left it and started building random things and after that, I built WebGames, NPM packages, VSCode extensions which helped me a lot in understanding the core.

Now I am in my final year of engineering and I've had some of the biggest achievements of my life because of these random things I built and I am very proud of them. Also, I interned at an e-commerce company and I loved the culture. It was the team of some really talented people and they taught me a lot of things.

So yes I am going to pass out next year and probably going to join a company and do a job.

Also, throughout these things, I had the advantage of being a student so I never really had to worry about the money so moving from freelancing(which was paying me) to open source(which did not pay me anything) was worth it because of all the knowledge I got and things I built.

Thank you for sharing your story!


Thanks for sharing your story too! :)

My advice would be to do your research and not necessarily join the first company you can if it doesn't feel right. I have turned a few companies down in my time before and looking back am really thankful for it.


I love that this industry has the flexibility to be salary or freelance. Different strokes and all that. Very few careers like that exist. Personally, I think I'd be happier as a freelancer. But I need to learn more first. I'm glad I have the potential option to learn at a company and then move into freelancing if I want.


Yes for sure.

We are lucky that in this industry we can get everything from a really corporate job, to something flexible or completely go it alone. Developers have it good.


Its hard being a lone wolf :) Do you have the option of being back in a team?


Not right now. Maybe in 2-3 months from now. Thanks for the words. 👍

Awesome! Thanks for sharing your story as well.


I’m not sure why freelancers give other freelancers a hard time when they decide to leave. Nothing wrong with that! Sometimes, it’s not providing fulfillment anymore or freelancing was just a temporary opportunity that you needed because you didn’t have choice in doing (you couldn’t find work, where fired, etc). If I were offered a job where I’m going to experience advancement in my skills with a guaranteed paycheck and benefits, then I would drop freelancing in a hot second too.

I agree with you about freelancing. I didn’t get into freelancing because I wanted to, but HAD to for me to pay the bills (I couldn’t find a job after graduation to save my life). It wasn’t for me and I didn’t like it. I now work with an awesome company as a medical writer and I have zero regrets. I don’t see myself going back to self-employment anytime soon. Chasing invoices, ghosting clients, clients that change their mind and decide to work with someone else, the stress of finding more work, and the deterioration of skills (I was doing the same thing over and over plus spending most of my time and efforts finding new clients). I can go on and on on why freelancing is not as great as people take it to be. Thanks for sharing! We need more articles like this.


I couldn't agree less, I have the exact issue not able to learn new things. I just started job hunting again. Wish me luck.


Good luck in the job hunt :)


Your Gary Vee line is Gold.
I discovered Gary Vee is mainly for those in their early 20's.
He is really useful at that period because of the fire and drive he generates.

Really good read.


Yeah I agree, I think some people live too closely to his advice. I find elements are relevant, but he (to his own admission) contradicts himself sometimes.



Couldn't agree with you more my friend :) Thanks for your reply 🙏