Forgive me, I should have written this guide sooner in the pandemic. Just didn’t think it would really be needed. But now that the global pandemic is a permanent thing for a while, and so many of you are clamoring for some of my work-from-home magic, I will share my tricks of the trade.
While a 9-5 job wage-slave working remotely can benefit from some of these tips anyway, this guide is written for the freelance / professional point of view.
[1] I’m sorry, you need self-discipline.
Do me a favor: Take a deep breath and then scream “GATEKEEPER!” at me as loud as you can. Now that we have that out of the way, I’m sorry, but nature imposes this gate, not me. Either you are a self-starter and able to discipline yourself, or you will fail. If you say, “I can’t self-dicipline,” make yourself do it. Learn how. Give yourself a new chance, maybe things have changed.
Of course, there’s days when I don’t want to work, there’s tasks I dread, there’s deadlines that I procrastinate because, to be frank, it’s fun and I perform amazing under pressure. But I get the thing done! It always eventually comes down to “it is time to sit down and plow through this unpleasant task.” There are no shortcuts, no tricks. Just start doing the work and let the momentum carry you. Really, you were doing the same thing for a boss when you worked 9-to-5. Now you get to reap the full spoils of your labor, so that’s even more motivation, right?
Wanting to work from home without self-discipline is like wanting to be a lifeguard without learning to swim.
[2] Never put your eggs in one basket!
Keep them in ten baskets, with another ten on hand in case you need them fast. Since freelancers have no job security, I can not fulfill 40 hours per week for just one client. If that client gets hit by a bus, I’m out of work and it takes me an average of four months to replace a client. The biggest slice any client gets is 25 hours per week, and after that, the slices of my schedule go in smaller ratios, dwindling down to a few minor boutique projects at maybe a few hours per month.
The big secret to this method: I can have a client blow out, and keep that slot open while I work other clients and get by on their money. Eventually I replace that slot and I’m back to even Steven. Clients have quit me for all kinds of reasons: One got promoted out of the position where she needed me; another had a death in the family and had to leave the entrepreneur life to go run the family business. I was kidding about the bus, hasn’t happened yet (knock on wood).
[3] Use corporate-speak when negotiating work relations.
There is a very good reason why so many MBA grads use that slippery, weaselly language that deflects all responsibility into limbo: It works.
How do you tell a client that you wouldn’t work for them if it meant getting out of hell? “Thank you for your interest! However, I do not feel that I am the right candidate for the position you describe.”
Is their offer too cheap? “I’m sorry, I’m afraid that I could not stay in business if I allowed my rates to go that low.”
Client ask something unreasonable? “Unfortunately, I’ve had to set a policy in place against that for business purposes.” See how beautiful this is? Just because you are a sole proprietor, that doesn’t mean you owe the world any more explanations than your average corporate mouthpiece. You had a meeting with yourself and formulated your company action plan, OK?
One time I turned down an outrageous proposition with “I brought this up with Tabitha at a meeting this morning and she feels that the downsides outweigh the upsides for this caper, and also we’d never walk it past legal.” Tabitha was my cat at the time.
[4] You are also your own best client.
The only rules are the rules you write! That’s what we freelance hacks love about this lifestyle, that wind in our hair. So use your best resource: you. Track your time, optimize your earnings per hour, measure what works and doesn’t work about each project. The more skilled you become, the more skills you can fall back on instead of outsourcing.
Likewise, make “business skills” a class of skills that you learn. There is a reason why MBAs are so common in business, because that degree covers basic business skills. Things like accounting, project management, communication, time management, and problem-solving are all covered under an MBA.
I understand, you hate all this icky business stuff. Part of the reason why I work as a creative freelancer is so that I can be the wild artist in the tower churning out my magic inspiration, and let somebody else worry about how to turn it into money. But I still have to understand enough about business, because at the end of the day I am my own MBA and nobody is going to care about my continued survival as much as I do.
This is a big stumbling block I see a lot of people trip over. When you have a wage-slave job, you get to look at a problem and say “not my responsibility.” You don’t get to do that when you work for yourself. Everything is your responsibility.
“Being your own boss” also means “being your best employee.”
[5] When interviewing clients, YOU are doing the hiring!
In the beginning, you will of course be grateful for any old rat who throws you a few dollars. Go ahead, sell it cheap while you’re building up. Put up with some edgy, but tolerable, clients while you take notes to learn from later.
After you’ve got your feet wet, you get to drive negotiations. What does this mean to you? You want long-term clients, with years-long contracts. The kind where you trade Christmas cards every year and your family gets to know their names. To get these kinds of clients, you need clients with a VIABLE BUSINESS MODEL.
Clients need money in order to pay you money. Amazing, I know, right? So you want to work for small businesses, white collar professionals, and entrepreneurs with a proven track record. As you go along, interviews with clients will become less like an employment screen and more like an episode of Shark Tank. They have to convince you why contracting with them is beneficial.
For my smaller scale clients, sure, I’ll take a chance on a long shot. For your biggest time slots, you want small businesses, proof of income, a realistic expectation of earnings. Do not be afraid to ask a client “How does my work profit you?” If they have a website, is it making money from ads, affiliate links, selling products, collecting referrals, what? Don’t bet all of your whole career based on a flimsy business model.
Relax! You can afford to be picky.
Let me make this clear: You will never run out of clients. There are an infinite supply. People might ask “Why is this guy telling you the secrets of his trade if you’re just going to compete with him?” Bring it on! Compete with me! There’s room for more freelancers at my level, plenty of room.
Therefore, once you get solvent, once you get multiple clients going, you can afford to turn down work if it’s not profitable enough or smells fishy.
[6] What to do during downtime? Learn!
The more skills you have, the more you have to offer per client hour. Seriously, I have no problem diving into source code to fix something if I have to. All the popular office tools and online services? Learn ’em. Any skill you can conceivably sell online with your clothes on? Might as well pick it up, especially if it’s adjacent to a skill you’re already good at.
Ideally, you should not have that much free time except when you’re just starting out. But even when you have a full dance card, carve out a few hours for you. The more you learn, the higher salary you can command, and then the fewer hours you have to work while making the same money. So you use that extra time to add more skills…
[7] You also have to do the jobs you hate, too.
If you’re in business for yourself, you are your own accountant, janitor, and marketer. I loathe marketing with a passion, but I have to resign myself that it’s a necessary evil. Without marketing yourself, the world will pass you by.
The accounting and business management is a hassle too. A chunk of my week is eaten up with invoices, emails, tracking, Zoom meetings, reading memos, taking notes, and all the mundane trivia that goes along with any office work. If I ever do get built up enough to outsource labor of my own, the first thing I’d like is a damn secretary. “Here, read through this email chain and nail down when this project’s deadline is.” That would be heaven!
But you gotta do it, so you gotta do it.
[8] Avoid burn-out in two ways…
Yes, we’re only human. We all burn out eventually. I am a workaholic and left to my own devices I will work until I collapse, sleep until I wake up, and chain myself right back to the desk again. But if I do that in the long term, my work suffers! I get dull and repetitive, make stupid mistakes, and make bad decisions because my stressed-out brain clouds my judgment.
So I learned the necessity of taking time off. Normally that amounts to one day off per week, usually Sunday, because most of my clients observe some kind of weekend anyway. But that day will move around depending on schedule. The important thing is that I apply the same discipline to leisure that I do to work: Don’t just gel on the laptop all day, get outside! Get some other stuff done, some household chores, get out and run errands.
The second way I avoid burn-out is to take on some fun projects for the minor time slots. Like I said earlier, the big business clients take up the majority of my work week, but at the trailing end I look for easier, more relaxed work to take a breather. That’s why you’ll see me with such a diverse range of output. In a random week, my output might be an IRS business audit guide, a guide to organic chemical isomers, a forecast for the content marketing industry in the coming year, and a review of a horror movie. When the “dessert” project comes along, even though I’m only making coffee money off it, it’s work I can relax and enjoy – maybe even put my best flourishes into it so it gets me a little applause.
So do keep a couple small-time projects that you can still work on in your twilight time, when you can’t justify time off but also don’t feel like saving the world today. They will preserve your sanity.
[8 ½] A final, half-a-way to avoid burn-out:
However, I am also lucky in that I love what I do, even the topics you’d cringe at. I am of the philosophy that the entire universe is a fascinating place. I find some joy even in writing about IRS audits. I’m sorry, it’s just how I’m wired! I am a curious monkey who wants to learn how the whole universe works, and then I love to pass that enthusiasm over to my readers. I point to the wondrous and amazing parts. I write on hard, controversial topics. I present new ways of looking at issues. I champion for underdogs. I make sure that my work is ethically defensible.
Whatever your work-from-home niche, you will do better just by having work that you’re well-suited to, and maybe even can believe in a little bit. I have readers who write to me once in a great long while, thanking me because my advice in an article changed their lives for the better. I cradle those emails as I drift to sleep at night.
[9] Social support helps a lot.
There is not much you can do with this tip, because either you have access to support in your personal life or you don’t. Me, I have a loving marriage that has lasted 28 years. We raised four kids, now grown up and out there with their own busy lives.
I owe Mrs. Penguin a deep gratitude for my business situation, because I could not do it without her. Even though 90% of her contribution is just listening to me vent my frustrations or geek out about my latest project. That is an essential function so I don’t explode. We have little household / business meetings every week or so. She handles the details of the household, paying bills and setting appointments, so that I have more time to bash this keyboard. She deals with the muggles in the outside world and keeps them from pestering me. She pitches in on social media and marketing sometimes, and in fact has her own little influencer business on social media too.
The main difference I see many work-from-home starters have is that they miss the “office water cooler chat.” Now in the first place, if you consider yourself one of those disgusting “extrovert” people (ugh!), then working from home is not for you. However, even the most hermetic introvert needs some human interaction so they don’t start hearing voices from the kitchen appliances. This is why that stereotype exists of a freelancer working at Starbucks.
Bottom line, keep some kind of support network going. Working from home while living alone is basically voluntary solitary confinement. Working this gig long-term will make you feral enough as it is. Find a way to keep your needs met, even if it’s just a daily Zoom coffee chat with other work-from-homers.
[10] Real world experience helps a lot too.
Don’t think for a minute that, just because I’m a work-from-home guru now, that means that it’s all I’ve even done. Previously, well into my 30s, I worked the wage slave world because I hadn’t encountered my true niche. I hopped through a series of jobs, in a scattered checkerboard of careers and industries which make no sense if I tell them in straight order. That was me trying to fit into the “square” world. It did not take, but I did pick up a collection of experiences that apply to my work all the time.
So that might be one final tip, if you’re following all the rest of this and still struggle to work from home, is that you might be too young and inexperienced at life itself yet. There’s that “gatekeeping” charge again, but it’s a law of the universe not of my making. It’s easy to fix; just leave and come back later after you have a couple other jobs under your belt.
No, not everybody is cut out to freelance from home
It is not my purpose to discourage people from following their dreams here. But we do have to face a practical limitation, which is that freelancing as a sole proprietor takes a lot of diverse skills and a hell of a lot of chutzpah. When it comes down to it, I just sit at home and use my brain; checks arrive in the mail. How many people can even conceive of this level of economic voodoo?
To my neighbors, I am an enigma. I appear to thrive with no visible means of support. Up until the COVID economy, I found it impossible to explain to people what I do for a living. But now circumstances have forced a crowd into my previously private pigeon hole, so I am obligated to try to show some of you the ropes.
If this career were that easy, more people would be doing it.
