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by throwaway9191aa 1233 days ago
I made it for a little over 6 years as a full time freelancer before I went full time (about 6 years ago).

If you are going freelance to avoid getting laid off...

Since I became a full time employee I have actually gotten paid every month (almost never happened as a freelancer). I have never had to find a new contract, or had a contract fall through after turning down other work. I haven't had 90 day payment terms.

I just never found that magical "pick up work when you want, and actually get paid on time" sales pipeline. You are not your own boss. You have clients, who have deadlines, who are paying you to meet those deadlines. If you don't, you suddenly find yourself in violation of contract law. At your full time job if you miss a deadline, how often do you get fired? That has never happened to me. But I have absolutely not been able to deliver on a contract and not gotten paid because of it. Once a client thinks "We don't actually want to move forward with that project", they try to find a way to get out of the contract. There are no severance packages for freelancers. Just months of wasted time that won't be compensated.

12 comments

On the other hand I have been freelancing for the past 10 years after 15 years of working as an employee.

I no longer need to burn certain amount of hours in front of the computer. My compensation is based on my results. This is probably the biggest change that happened for me -- it allowed me to think about my overall performance as something I do and optimise for myself.

Another thing is that when you work as an employee you are getting bunched up with other people. This is fine if you are an average, but if you work every day to excel and improve your performance you are doing yourself disservice because you are subsidising all those other people who barely pull their weight or don't do it at all. My results are now tied to me and my image and people notice, tell other people. It has landed me many jobs or improved my negotiation position a lot.

Another one is I no longer fear of loosing a job. When you move from place to place regularly it becomes part of your life and you no longer fear it. I became much better at negotiating and interviewing. When I join, I immediately set up an appointment with my overseer to lay out rules that will maximise my productivity, speed up my transition in but also my transition out of the organisation. For some reason being cool about leaving and planning to make the most of it for both sides does wonders to how the manager will treat you.

> Another one is I no longer fear of loosing a job. When you move from place to place regularly it becomes part of your life and you no longer fear it. I became much better at negotiating and interviewing.

If you're an employee, you can get similar results changing up your job every year or two. Maybe slightly longer if you really like the place.

Even in the "recession" recruiters are knocking on my door fairly regularly, and I'm comfortable enough with the Leetcode circus to be able to pass an interview loop. I'm sure some people will vehemently disagree but I notice a clear difference between my peers that only have experience working at 1 or 2 places, and those with experience working at 5-10 different places with different cultures, stacks, etc. It's obvious that the former are in a bit of a bubble and get blindsided in hard times or when there is a big technology shift.

> you can get similar results changing up your job every year or two…

This might work for few jumps but eventually Hiring managers will see this pattern and flag you as a flight risk. Please Take this advice with a grain of salt.

Only if there are a lot of 1 year stints. HR these days expects people to change jobs every 2-4 years.
Yes. A decade ago it was minimum 3 years for individual contributors who are not super specialised in what they are doing -- if you worked for less multiple times in a row they would be asking for explanation. Now it is 2 years.

I will also mention it is different for contractors/freelancers and will also depend on what you do. I don't hide I change projects frequently.

What I do is I offer references to my past managers. I tell them I will give them references as long as they are happy to stick with me throughout hiring process until they make their offer conditional on me giving them the references and them being happy after they talk to my past managers.

I do this because I don't want too many people calling those guys. I think it is fair arrangement.

I am a salaried employee. My boss and I are in an agreement that I won't be just sitting in front of a computer to work 8 hours. My performance is judged by stuff I deliver.

I will admit that I have a hard time finding a replacement job, as most places have a fairly strict "on" policy.

I will most likely get my masters while I'm here and then figure out my next move.

The strict "on" policy is something that will depend on the job. At the start of my career I worked as a sysadmin and it makes sense to expect your sysadmins to be strictly available during working hours.

As a developer/tech lead I think I should be trusted to manage my time. There are times where I spend way more than 8 hours at work and I do no fuss about it and I think it is fair that there are times where my private life intrudes on me and it is now my turn to take advantage of the flexible agreement. Whatever happens, I take responsibility for my commitments (so no, no missing or being late to meetings without heads up).

I think atmosphere of trust is the most important part for a healthy organisation and nothing screams as "we don't trust you" as not being trusted to manage my own time.

So while I don't necessarily reject the idea of "always on", it is somewhat of a red light for me. It signals inflexible thinking and inability to deal with problems.

Yes, there are people who cheat and slack off at their jobs. Making it "always on" is a result of a lazy, unimaginative mind.

While you enjoy it and things are good, be sure to get your arrangements in agreed upon writing so when the political winds shift you're covered.
This is never going to happen if you want to work for any larger company. And even if got it in writing (which you will not), they are unlikely to honour it because couple employees somehow got it in writing -- you will be coerced to change it or fired or "managed out".
>when you work as an employee you are getting bunched up with other people

If you are the best on your team you should either be mentoring them as a senior or find a new job where you'll be challenged

Would you be willing to share those rules?
There are no rules set in stone. My job is to find a way to work with my manager but many managers don't know how to do it or don't expect a person to be open about many aspects that are on the verge of being taboo.

I am not imposing my style of working -- out of necessity it is the manager that has to set the rules because he/she can't have completely different management styles towards each one of their employees. Instead, I try to find a common ground that will make my manager extremely happy while also allowing me to keep doing what I want and what I am best at.

I found that just this single act of explicitly discussing our "partnership" sets me up for a much better relationship with my boss than all other people who are passive and just expect to be told everything.

I would agree to this. I think there is an idea that you become your own boss. In some ways thats true but mostly so you can say that to yourself or someone else. Your destiny is still controlled by clients. If you think about most things -- very few people are their own boss, there are always stakeholders who control your time spent.

It's also a lot harder to disconnect for a period of time to go on a vacation. You kind of always have to be on. I'm sure there are some people who can do that and hack that split but when you have to constantly make sure theres a pipeline of work you have to manage client inbound.

This.

Maybe you can disconnect more if you are single. Or with a SO, but not children.

Once you have a family, there's just a lot more demands on you. The safer, more secure route ends up being the more traditional corporate job.

I've found it's the complete opposite. Traditional corporate jobs aren't in the least bit safe for me and my lifestyle. As a freelancer, I have immense flexibility over when I work, where I work, how I work, and to certain extent, with whom I work.

If on a particular day my family or my personal goals win out on the hierarchy of priorities, not a big deal. Sure, if over time my overall quality of work suffers, a client is going to notice, and that's not great. But otherwise…I'm calling the shots, and to me that freedom is worth its weight in gold.

It's the difference between servant and subserviant.

The fact that your occupation is to perform tasks for clients does not mean you're not your own boss.

The relationship between you and the customers of your company of one employee is (or should be) really not that different from the relationship between you and the customers of your company of 2000 employees.

There is a relationship, and it is in your interest to care about what they want, but that doesn't make them your boss.

Them being your boss in your mind is something you choose to give them if you're not careful, not something they actually own.

They will happily let you think that they have a right to own your soul because they paid you a few dollars, but the simple counter to that is, do you get to own their sould because you paid them a few hours of work?

You're absolutely your own boss.

As a freelance contractor you have two full time jobs. One is finding new work and the other is doing the work. As someone who likes the variety and freedom of being able to contract and define what the customer owns while still building my own startups I thought it was a good trade off when I was young and wanted the experience. I have gained a metric ton of experience and been paid to travel globally. Now I’m older and glad I put the time in. I don’t expect I’ll ever need to do so again.
Many decades ago my dad started his own small business in insurance claims adjustment. He spent an entire year trying to get it off the ground, but the only client he was able to secure was his own former employer, and fortunately after a year they offered to just take him back on as a full-time employee again. He told me the stress of constantly searching for new clients (and trying to do sales etc.) was absolutely miserable, and the psychological security of a regular paycheck beat the slightly larger amount he was making as a contractor.
Yeah, this is what we're trying to solve at A.Team on a few fronts:

1) You get to work in teams on long-term, meaningful missions (we're request-only on the client side) and earn $100/hr+ on average

2) We proactively surface missions that are a great fits for you

3) We have guaranteed on-time payments for our network (we pay them every 2 weeks, no matter what, even if the client doesn't pay us)

The vision is essentially is that you can join A.Team, discover incredible teammates, and discover incredible work that fits your interests and passions with top startups and enterprise cos building transformative new products.

I would absolutely recommend freelancing to people who need to study to move up, e.g. doing Stanford online masters or MBA and can put tuition into taxes. Rarely companies reimburse full cost and as a sole proprietor one has a chance to write education off via taxes, i.e. no student debt and top-end education/network.
In the US, anyone can deduct tuition and fees- and even better than a deduction (or "write-off" for a business) there are some tax credits you can get, too. https://www.irs.gov/newsroom/tax-benefits-for-education-info...

I don't see how being a freelancer improves the tax benefit over this at all.

EDIT: I did find this: "If you are self-employed, you deduct your expenses for qualifying work-related education directly from your self-employment income. This reduces the amount of your income subject to both income tax and self-employment tax."

So perhaps in some cases if you exhaust the credits having a deduction from the self employment tax would save you a bit on the self employment tax. But I would think in most situations the difference would not be all that large. And if your employer would provide even a partial tuition reimbursement, that would likely eclipse any tax benefit from being self employed. All of it is very situation dependent, though.

I contracted with a single client for 3 years. It was as close as you could get to being full-time without being full-time.

Everything just had annoying overhead. I needed a CPA to do taxes because I didn't want to spend the mental cycles on it. I needed to buy, update, and manage my own systems. I needed to do my own risk management, compliance, etc, etc, etc. I needed to find my own healthcare.

All of this was possible. However, it just added another layer to work that was annoying and distracting.

When I started out I freelanced full stack web dev. I found the best thing to do was build a network (through pub meets, coworking etc) of friends and other freelancers who would funnel work to me when they were overloaded, and so there was always a constant stream of stuff to do, then once your rep and cash flow were good, start increasing your rates and diversifying the types of work you were taking on - some of the former kind, some being referred directly to clients, sometimes joining teams where people need the gas turned up for projects etc. I’m full time now but if I could save up buffer and learn more personal stability and discipline I’d maybe give it a shot again.

It really is about who you know.

People will happily fill your time if you can be depended on to figure stuff out and take problems off their hands for them.

Also mixing less well paid reliable and prompt income with higher paid income that’s more of a pain in the ass.

I've freelanced full-time on and off for periods of a few years throughout my career, and completely agree. There's a misconception that it's in some way "flexible". When it comes to things like taking holiday, you kind of have to just take them when the opportunity arises. This has made coordinating time-off with my partner who works a full-time job pretty difficult, as often a particularly well-paid or high profile project will come in that's hard to turn down. I've also noticed, at least in Europe, that my workload picks up considerably in summer when you actually want to take a break. I'm going back to a full-time job later in the year and looking forward to having scheduled time off and having someone else paying my benefits and dealing with all the paperwork for me.
(almost never happened as a freelancer)

You mean you almost never got paid every month?! Well, I hate to sound callous but that's on you as a business owner who got into some bad deals. I've been freelancing off and on, and mostly on, for much of my long career in web dev, and I've found ways to find and hold onto clients that (a) appreciate my work, (b) pay well, and (c) pay on time. Was that hard?! Yes, very! But I'm thankful I was able to get to where I am now.

Speaking generally:

The #1 problem people face getting into freelancing is still thinking they "work for somebody". You don't. You work for yourself. You have your own business, with your own goals. Your own schedule. Your own growth trajectory. You *seek out* the clients you *want* to work with to help you achieve your goals as the owner of the business. The fact you help your clients achieve _their_ goals is a side-effect of your business plan, not "the plan". If you end up with a client who isn't a good fit for your business plan, fire them and hire a different client. You're the boss. You are.

The primary concrete benefit I can see to being a freelancer is being able to put away more money for retirement than is possible in a 401(k).

Almost every other aspect seems like a worse deal to me than being a full-time employee, especially with the [relatively new] greater acceptance of remote work for full-time employees.

Freelance is all about your network quality. When I did part time freelance to bootstrap my career I too got my dose of difficult clients. Then years later, I did a switch from FTE to consulting, with a single high quality client, and it was basically just like any other job.

What I came to realize is that freelance is actually the lower end of the spectrum for consulting agencies. A client base for such work can range from mom-and-pop businesses to veterinary chains to big telcos, with stability and size of contracts being relatively proportional to how good your sales/business development pipeline is. Needless to say, it's all work up and down the spectrum, so finding that mythical work/life balance liberation is an akin to mastering an art form.

Yep, this was my exact experience. A 40 hour work week was a vacation by comparison.

https://www.brightball.com/articles/what-exactly-happened-to...