Are you a Freelancer or a Weekend Warrior?

If you’re contemplating freelancing but have some holdbacks and are afraid to make the jump, it’s likely you never will. Sometimes you’ve got to Just Do it.

That’s just kind of a reality with not just freelancing but any business really. Often I come across people who really want to freelance and might even envy those of us that do, but they always have a laundry list of reasons they don’t or are working towards a goal before they jump in the deep end.

But honestly the most common type of person I’ve met who will never make the dive is the Weekend Warrior.

The Weekend Warrior

Oh the weekend warrior. I have so much to say to you.

Let me guess: you’re trying to replace your income by working on the weekends and when you break even you’re off to the races.. time to start freelancing officially right?

So you’re trying to replace your income while putting in your 40 somewhere else? And you end up doing all your work in the evenings and on the weekends?

First, you’re going to burn out before you ever hit your goal. Working 80+ hours a week doesn’t mean you actually did that much work. But before you realize this you’ll slip down into a whirlwind of constant errors in your code or mistakes you made on projects while letting clients boss you around.

Second, let’s say you make 50k/year now, it shouldn’t be that hard to hit 50k right? Well it took me just over 2 years of working full-time for myself to hit that mark. How long is it going to take you if you can only dedicated 20 hours a week to it (which is alot on top of your 40)? In the beginning I worked 50+ hour weeks very regularly. If you were on the same track it would take you roughly 3x as long.

But don’t forget that you’re then making 100k/year. And probably spending like someone who earns 100k/year — well, when you’re not working.

Third but really really important, a massive chunk of potential clients are only available in a 9-5 type capacity. How will you hop on a call with a client about their project if you’re sitting in a meeting at your day job? You won’t.. and they will move on to someone who is actually available.

So you probably get stuck taking low budget projects for crappy clients that will deal with that, because like most low budget clients they don’t really value what you’re producing. Helloooooo scope creep and hand holding.

/rant over

Making the Transition

1. Save Up

If you’re really smart your goal shouldn’t be to replace your income until you feel comfortable switching gears. Instead, try to save up a cushion of living expenses while getting everything prepped. I’ll talk about that next.

In past blog posts I’ve talked about being prepared if work slows, the same thought applies here. Assume you’ll have no work for a few months. The more the better but know when it’s time to make the switch.

2. Get Ready

While you’re saving up it’s a good time to start getting systems in place and legal stuff out of the way.

Here’s a quick rundown of a few things you’ll need to do and what I consider the most important…

Register your business (yes, you ARE a business!) as whatever flavor you like, but Sole Proprietor is likely to be the cheapest option, though generally offers the least protection. Most people end up as LLC’s, which I would suggest but you should speak with a CPA anyway since you’ll need help doing taxes and making quarterly payments, along with tracking expenses and knowing what you can and can’t deduct. Plus I’m not an accountant.

Setup a bank account – I imagine some people operate out of their personal checking accounts but you’ll need to be able to accept checks (yes businesses still use those) in your business name once you’re formalized, so don’t forget this important step because this is what it takes to work with real clients. Not everyone is going to pay your invoice via Stripe. Plus it’s what you should do.

W9 and Contracts
At the beginning of every year I prepare a new W9 form to have that years date on it, sign it, and save it in PDF. So if a client asks for a W9 (and many will) you’re ready to go instead of fumbling around – this could put a hold on any payments they make to you so I like to get it to them or their accounting department ASAP. Plus you’ll always get a few clients that come to you at the last minute before they file their taxes asking for one.

Get your contract in order. It’s so incredibly important to contract up when working with clients. It’s not an insult and I’m not sure why some people get that train of thought because it protects both you and your client.

I suggest Contract Killer if you’re just getting started. No need to go all out for a custom contract just yet, but eventually you may want to consider that. CK misses a lot of things that are important like project delays.

Get your marketing in order – Having a website is probably crucial to what you do since designers and developers are generally my main audience, so you probably already know this or have one. Especially if you’re already doing some work on the side. But does it look good or did you slap it together? Yeah, me too. Done in a day right? I get it but it’s probably time for a revamp. Update your content with the work you’ve done unless you have some really choice pieces.

Find some space! – If you can afford it dedicated work space outside of your home is awesome. It doesn’t have to be a private office theres plenty of Coworking spaces out there! You can always work out of a coffee shop if you had to, but make sure you have a space to work from when you need to get out of the house and focus. I hate routines, but maybe setting a schedule and sticking to it will help you feel as if you’re actually going to work. It’ll make your transition feel more official.

Spread the word – Reach out to any clients you’re working with currently or past clients and let them know when you’ll be available for freelance work in a full-time capacity. Once you officially seal the deal and leave your current position, make sure to let EVERYONE know what you’re up to. Trust me, it will help.

You also might want to try reaching out to local agencies, attending meetups, and networking with other people doing what you do. There’s no shame in asking someone more seasoned for coffee so you can pick their brain. Most people are really proud to talk about their accomplishments and they may even have leads on work they could send you since you’re just getting going!

3. Be Confident

This is what you’ve worked towards. You wanted to call the shots, run your own business, and work on projects you think are meaningful. Well the last part is going to take awhile since you should be hungry for work and grabbing just about everything you can right now. But be confident in yourself that you’ll make this work. Hustle when you have to cause nobody got anywhere by being lazy.

If you really wanted it you would go after it.

Stability is cool and that’s what most people need rather than want. But if you honestly wanted all the freedoms (and long hours) that come with running your own business, you would probably already be doing it or well setup for when you do make the move.

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  1. Jimmy Smutek says

    Great post, thanks Drew. It was kind of a relief to hear that it took you 2 years to start to get to a comfortable level of profitability. I just wrapped up my first year – I was profitable but only because I have such low overhead, and definitely nowhere where I need to be.

    I’ve got some plans for this year that include new branding and a greater level of focus on a niche audience, so I am excited to see where things go. I’m excited to see where things go this year.

    CK misses a lot of things that are important like project delays..

    I use CK – It would be cool to see what you use as a clause for project delays, if you have the time, and don’t mind sharing. It’s something that is not in my contract and something that I am dealing with on one project currently. It’s driving me a little nuts.

    Also, by way of request – I would love to hear more about how you and your business made the move from Baltimore to the west coast. Your story is super relevant to me as my family and I are trying to make it out to Hawaii in the next two years, and a big part of that plan is contingent on my building a profitable business that I can move with me.

    All the best, thanks for this blog and the good information that you share.

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