Freelance, Contract, Full-Time Hustles
Some of the pros and cons of each, as well as where to get started.
Maybe you’ve heard of Tim Ferris, and dreamed of the 4-hour work week. “Sipping Mai-Tais on the beach,” you think. “That’s what I’ll be doing today.” You check you email from your pool chair on this hypothetical beach, and dollar bills start falling out of your open laptop screen into your drink. Your personal attendant is quick to pour you a new one.
Is this just an impossible daydream? Well, no. You actually can work your way to automated revenue, and we’ll talk about that later. But more likely than not you’re closer in life to being the pool boy than the millionaire beach-lounger putting in another “rough day at the office.” You might have an end-goal like that in mind someday, but first, you have to put in the work. Come on, pool boy, break’s over!
Finding your niche
I’m a white collar, Sr. (or Lead, depending who’s asking) web developer. I’ve hustled hard to get to this part of my career so quickly, but I didn’t start here — and what I do for a living might be suffocating for you. I collect salary, have regular hours, collect a constant paycheck and sometimes work from home.
Maybe being chained to a desk, being a corporate cog, sounds awful to you — maybe you’d rather find that beach somewhere. Let’s talk about how to get you there, and what it’s going to cost to get there.
1. Freelancer, Master of His Own Fate
You didn’t even finish the first two paragraphs and you were already packing your laptop bag and looking up flights to Peru. The wild, remote life of a freelancer appeals to you, and wherever a Caribou or Starbucks can be found, you call home. While it is true that this option affords you the most freedom to work where you want, when you want, and for who you want, there are some things to consider.
Pros
- Freedom and flexibility on when or how the work is done (3 hour lunch break to play DOTA? You’re the boss!)
- Potentially lucrative, as you set the prices for your services
- Variety and Flexibility that comes with working on so many unique client projects — you could be working on a blog this week, and a shopping cart the next
- Work from the comfort of your own home, or coffee shop, or beach with wifi
- Get to work with a variety of cool clients
Cons
- You are your own boss. You’re also your own sales department, your own accountant, your own tech support… You’re also designer, developer, Sys Admin…
* You’re on your own here, which means that you get to call the shots — but if something goes wrong, it’s all on you to fix it.
* You’re also going to have to keep track of your own financials. No one’s handing you a paycheck, you will have to issue and track invoices in order to guarantee cash is coming into the bank. - Potentially unprofitable, if customers are scarce or talk you down on your prices
* This is something that keeps every small business owner up at night — there are rainy and dry seasons for work, and no guarantee of when the next customer is coming.
* You might need to do this as a side-hustle or have multiple jobs ongoing to stay financially secure. - Easy to get in over your head
* A customer has a simple website, but wants to start sending out a newsletter. Were you expecting this from the start? Now you have to worry about collecting email addresses, composing emails, and sending them back out. If you’ve never done this before, it’s going to eat up your days, nights, and weekends until you get it figured out. - No coworkers, no office… no escape
* I have worked 100% remote from a company before. At first it was great — I didn’t even have to get dressed to start work, and I would stay up binging on netflix until the early hours of the morning. But after a while, a claustrophobic feeling started to come over me; my bedroom was also my office, and any time I was at home I felt compelled by guilt to sit at my desk, or check emails, or do more work. Eventually I felt trapped in my own home! - Clients from hell.
How to get started
This is going to take some work on your part. See if you need to establish yourself as a business, build your portfolio page, and starting knocking on doors to find clients. You’ll be nose-deep in as many business blogs as you are developer ones. I wish you luck!
2. Contractors, Mercenaries For Hire
Did I scare you away from freelancing? Maybe you’re stuck in the middle, repulsed by the idea of being chained to a desk but also scared of ending up on the street. Being a contractor/consultant is a pretty happy medium, for a number of reasons.
Pros
- A mix of stability and variety
* Contracts typically last between 3 months and 2 years. When one contract ends, you’re free to pursue other opportunities. This allows you the chance to experience a lot of work environments, and figure out what kinds of companies you like to work for - Make lots of connections
* Most developer communities are pretty isolated. Working at many companies as a contractor allows you to connect to other developers at every stage of their career and might potentially be people you get to work with again someday - Very lucrative
* Contractors make big money. There, I said it. You can expect to make more per hour than your full-time counterparts, for enough reasons that I’m going to save them all for another article. - Good work/life balance
* Something unique to contracting is that typically contractors get paid per hour. If you’re on your own time or work salary, expect to have to work well over 40 hours during “crunch time.” Once you’ve worked your shift, you’re free to leave work at work and call it a day. - Quickly advance your career
* If I seem rosy-eyed about contracting, it’s because I went from entry-level to lead developer in under 5 years. I doubled my salary! Freelancers get paid based on the difficulty of the project, and salary workers get paid based on a position with a yearly raise. By hustling hard, I was jumping between 5 and 10k per contract - Recruiters
* Recruiters, the frenemy of the contracting world. Treat them well, and they will open the door to great job opportunities, buy you coffees/lunch, and offer you some of the perks you might expect from working full-time with a company. Look out for advice about dealing with recruiters in a future article.
Cons
- Less stability
* The unpleasant truth behind why companies use contractors is that they are easier to bring on/let go. You may find out your contract is ending with just a week’s notice (or less!) so make sure that resume is up-to-date and get some enjoyment or thrill out of the job-hunting and interview-having phase of employment. You’ll be doing it a lot. - Fewer deep work connections
* For companies that have contractors, don’t expect to always receive the warmest welcome from full-time employees. They’ve worked with each other for years, so they have their inside jokes, happy hours, and family bbq’s. You might not even be there next month, so you won’t always get the time of day. - Poor Benefits
* The trade-off for making more per hour: You’re in charge of your own benefits. Consulting agencies may offer provisional plans, but if you need quality insurance that stays with you from contract to contract (or agency to agency) you’re on your own. But you’re young, and invincible, right? At least, you hope so, because contract workers don’t often get PTO days for sickness or vacation. All of this is manageable, but they are things to keep in mind. - Miss the company perks
* Is the team calling it an afternoon and going to a baseball game? Or having a raffle drawing for prizes at the Christmas Party? You’ll hear about it, maybe even have stand outside the window with your puppy dog eyes, but perks like these are some of the few that salary employees have. I wouldn’t share, either. - Recruiters
*What the whole video, because this will be your life:
How to get started
I talked about this elsewhere, but you need to convince recruiters as well as the business you’re interviewing for that you have the right skills for the job. Launch your portfolio site, polish your linkedIn profile, and start applying for jobs on sites like dice or indeed. Don’t worry about trying to find recruiters — they’ll find you.
3. Salaried Professional, Living Dilbert Cartoon
Corporate Sell Out. Office Drone. Code Monkey. And did you finish those TPS reports?
But it’s not all bad.
Pros
- Stability
* Guaranteed paycheck on time, every time. No dry seasons, no gaps between contracts. - Perks
* Some companies are way better at this than others. I went from one company that paid their developers to attend conferences and had a fully-stocked snack pantry (and soda.. and beer fridges) to a place with no holiday parties and we had to bring in our own coffee. Companies often can use collective bargaining to get things like store discounts or free swag for their employees. - Benefits
* Just starting out, I wasn’t worried about things like insurance or retirement — several years later, I’m a married man with a child to take care of. It’s possible to handle things like health insurance and retirement as a freelancer or contractor, but without a company to help cover some of the cost of these things, it’s all going to come out of your pocket. See if the company offers 401k matching or other retirement benefits. - Family
* Your team is made of people you’ve worked with for years, and you’ve gotten to know them as comrades, and even some of their families. You commiserate about the same work problems, but you can all handle it together. You’ve got each other’s back.
Cons
- Boring
* If you are the type that craves variety, it’s inevitable that supporting the same software application for 5+ years is going to leave you bored, fidgety, and looking for other opportunities. Whether you keep an open eye for new jobs or stick it out and play it safe is up to you. - You lose your edge
* Big ships are harder to turn. Your managing team spent 6 months researching frameworks before deciding to upgrade javascript libraries, and two weeks after you switch, you find out it’s no longer popular and liable to become unsupported abandonware. Someday when you do decide to jump ship for a new opportunity, you’ll remember that you haven’t had to interview for anything in years. And when they ask about your current job, all you can think about is how you’ve solved the same problems with the same frameworks for as long as you can recall. - Meetings, company politics, corporate way of life
* Full time employees are subjected to not only the daily meetings about current projects, but also the meetings about the company itself — shareholder meetings, quarterly reports, on and on. Might be a good day to work from home.
How to get started
You’ll actually follow the same steps as contractors do, but with one caveat — companies are willing to take more chances on a contractor than a full-time employee. They can let contractors go without a second thought, but when it comes to firing a poorly-performing, salaried employee.. HR has to get involved. If you want them to take a chance on you, you’ll need to wow them.
4. Entrepreneur, The Wildcard
This whole time you’ve kept that Mai-Tai pouring in the back of your mind. Aren’t there other options than just these 3 paths through life? Yes, I’ve only listed the most common types of careers. There are companies that work 100% remote, or collaborative collections of freelancers working together on a per-project basis. But maybe you’re only interested in getting to the top, living a jet-set lifestyle of semi-retirement as automated cash just flows in. It’s possible, but you’ll have to hustle impossibly hard to get it.
I can’t talk about pro’s and con’s because each entrepreneur’s experience is different from the next, but here are a few points to consider:
- If you aren’t a business guy, you better be a developer
* While it’s true that an app like flappy-bird or minecraft can take off and make a fortune, it’s more likely that an app is successful due to a sound business strategy behind it. If you don’t excel at one or the other, you’re going to need to build a team that can cover all the bases - Beware the webinars
* Bootcamps, seminars, life coaches, training camps: All promising business success, all free at first, but eventually they will all try to turn your hype into their profit — sometimes to the tune of thousands of dollars. Sign up for the newsletter to get the free e-book of advice (I do!), but don’t let yourself get suckered into a program that can’t promise any actual results or you might end up embroiled in the next Trump University - Try anyway, even if you probably won’t succeed
* Nothing helps you learn faster or stand out better during an interview than proven ambition. Being able to show side-hustles I’ve worked on and personal projects in my portfolio has helped seal the deal on contracts I’ve worked in the past that I was nowhere near qualified for. And who knows, you might strike it rich!
There are a lot of ways to make a career in web development, hopefully now you know which one you want and how to get started. Happy Coding!