Freelancing is Hard

But it doesn't have to be

I have been working since I was a child. I would work in my mother’s office in Manhattan every summer, mostly in the mail room. I would organize and deliver mail within the office. Crazy, right? Why not use email? Well, it didn't exist yet.

Since then, I have never really stopped working. During those 30-ish years, I have worked dozens of jobs. During all of that working, there has always been the side-hustle, the gig, the freelancing job. I have always been drawn to having a side-thing. This role has been simple – selling things on eBay, or complex – creating films for athletic companies. Over the past few years the lines have blurred though. After I quit my day job in 2021, my freelance life and traditional work life are very mixed.

I have not officially worked for anyone since 2021 and it has been kind of amazing. I set my own hours, I determine my current rates, and I choose who I work with. Sure, I don’t have PTO, health insurance, or other traditional benefits. I am lucky in that sense – my wife has a traditional nine to five. She provides the health insurance and other perks.

In my current freelancer, entrepreneur form, I am a digital operations consultant. While that title sounds vague, it is quite easy to explain. I am the person you or your team hires to systematize and refine all of your digital operations. The focus is usually centralizing all of your company's information into one place. This limits context switching and clarifies what information lives where.

I do this both as an entrepreneur and as a project owner at an agency. Either way, I don’t see it as I work for anyone. The agency is just another client. With the agency, I get to work with larger clients and with a diverse team. The clients expose me to their, often complex, problems. The team helps me learn interesting ways to solve them. The really nice thing about working with them is that it has been the polar opposite of any traditional job I have had. This might be due to me being one of the oldest contractors on the team or that there is no corporate bullshit. You just get shit done.

So why is freelancing hard?

Inconsistency

I thrive on trying new things and being in a liminal space, but the inconsistencies of freelancing are something else. When you work for yourself, in a consultative format, you generally don’t have a consistent revenue stream. Some months you are chasing your tail with endless inbound calls, tons of new client projects, and those lingering retainer projects. Other months you are wondering if and when your next payment will come in.

Above, I mentioned the lack of benefits. This only adds to the inconsistency. If you need these things, it can make it even more stressful. You might not be sure if you can go to the doctor or get the meds you need. I’ve done that in my 20’s, with little problems, but I can’t imagine having to go through that at 36 years old.

Balance

When working for yourself it is extremely challenging to set a definitive line in the sand of when you are working and when you are not. I have tried to have a work-life balance. But after years of trying, I don’t think it is really possible. During those months that you are chasing your tail, you’ll have to put in extra hours, respond to client emails from your phone, or take a Zoom call from the car. It is truly hard to avoid.

How to use these difficulties to your benefit?

Diversification of income

Don’t focus all of your energy on one revenue stream. Spread it fairly evenly over a few. Some people do this by selling other services, like templates or courses. I do recommend this, as they are great ways to not only generate revenue, but also convert people to clients. A template or course can lead a person to your sales funnel, which you then convert to a client or better yet, a lead to the company they work for.

You can also approach the situation like I have. You can work with an agency and for yourself. I got the idea from journalists. It is common for a writer or journalist to write for themselves and numerous publications simultaneously. This gives them a way to do what they love, but actually make a decent living.

The key to this is to not think that you work for that agency, in a traditional form. You work with them, they are essentially another client. This provides you the autonomy and freedom to think and act for yourself. By doing this, you keep an entrepreneurial mindset. If you don’t, you might get caught back up in the nine to five mindset, which will likely make you second guess your business and not stick with it for the long haul. Diversify the income streams, but identify as a freelancer.

Ask for your worth

Money is always a tricky topic. We all work in varying fields. You might be a designer, a developer, an executive assistant. While these roles vary a lot, they are all specialized and can yield high salaries if you are great at what you do. So never feel shamed for asking for your worth. As your skills change, as you master a new system or coding language, change your pricing. This doesn’t always manifest in raising your hourly. In most cases, I recommend staying away from hourly. But always be reevaluating your cost. It should be changing regularly, because you are always changing. If you charged $50 an hour 12 months ago and you’ve been freelancing consistently, you need to up your rates.

Revel in the slow times

When you are not burning the midnight oil, you’ll be watching paint dry on that chair you’re restoring. This is ok. In order to keep burnout from encroaching on your life, having times of extreme downtime is complimentary. I would honestly recommend fostering these times, almost planning for them.

Regardless of your success as a freelancer, lulls are inevitable. So why not integrate them? Rather than have your life turned upside down every 2-3 months, take a few weeks off every few months. Freelance work is a different beast than a nine to five. You don’t have to, and shouldn’t, squeeze in 8 hours a day, 40 hours a week, for 50+ weeks a year. In order for you to wear all of the hats your business requires you to wear, you need to make sure they fit, and they will not if you're burnt out.

This also benefits you financially and organizationally. If you plan for these times, rather than wait for them to crumble on top of you, you can control your budget and timelines of projects. It makes your work repeatable, scalable, and controllable.

Work-life harmony

While making my film series, The Gray Area of Remote Work, I stumbled upon the term work-life harmony. While my mind was blown by the concept, its importance didn’t hit me until a year or so later. We hear the term work-life balance being thrown around constantly. While the concept is great; in reality, in 2023, as a remote worker – it’s not realistic. Most of our work is done with our minds, on computers, or even from our phones. This means that work is not only within reach, it is expected. In our capitalistic society, time is money, and the time was yesterday.

I recommend leaning into it, but set some healthy constraints.

First, leverage downtime, as I mentioned above. Work hard and often during your busy times, but disconnect as much as possible when you can. I really love the idea of think weeks. Popularized by the likes of Bill Gates and Warren Buffet. A think week is a period of time that you take, for yourself, to allow deep reflection. As knowledge workers, a fully disconnected vacation is not always ideal. So the idea of taking time away from your projects, but keeping your mental wheels turning is alluring. I haven’t tried this method yet, but I plan on it soon.

Second, allow yourself to work nights and weekends, if you need to. I don’t mean “grind your face off”, working all weekend and ignoring your loved ones at night. What I mean is, don’t fight it for the sake of morals. If you need to reply to some emails or watch your notifications because something just launched and you need to keep an eye on it, do it. During that wave of work, it is high priority. Just make sure to deprioritize it when it’s time.

Lastly, let your tech force your intentionality. If you are in the Apple ecosystem, use focus modes. I have a simple time-based rule on all my devices. During my working times, I see my work emails. When it’s outside of that time, I only see one; personal email. I do this by using Apple Mail, loading it up with all my accounts, and enabling focus modes to filter them out. Yes, I know, all the tech bros shudder at Apple Mail. I don’t need fancy features, I just need my email on my devices. Human controlled productivity. Sure, I do push through occasionally and peek at the full inbox, but I don’t shame myself anymore.

Wanting to be a freelancer generally means you are wired differently. We are like the ultra marathoners that love the fight. Freelancing is not predictable, it bleeds into your personal life, and there are little to no traditional job perks. But working for yourself is something else. If you are a person that revels in being an entrepreneur, full or part time, know this – it will be tough. But, the benefits far outweigh the downsides. Like a marathoner, if you set yourself up for success (practice and recover) it won’t feel as hard as it should.