5 Apps Every Creative Business Needs to Get Their Shit in Order (With Extra Love for Non-Planney Types)

Planning is not my strong suit, by which I mean if you come anywhere near me with a “party planning checklist,” I will immediately grab a knife.

It’s instinct—you know, like the repulsion you feel when other species eat their young?—which probably also explains why, when I go to the grocery store, I end up leaving with forty-nine boxes of cherry-flavored condoms. Not on the list, but how can you not?

It’s also why I’m persistently late at present-giving. I am absolutely that person buying your Christmas present online, the day before, and then paying the equivalent of a small trophy horse to have it overnighted—even when I optimistically write stuff in my calendar three months prior that says things like “BUY PRESENT NOW, YOU FORGETFUL FUCK.”

Then again, the American in me makes me slightly better at planning than, say, my Costa Rican counterparts. (If you’re just catching up, we have a place in Costa Rica where you can find me crushing the dreams of spiders jungle-wide.) If you tell me that somebody’s coming over today, I need to know at what time. This seems like a reasonable request, but it’s unlikely to be recognized. “Ahora mas tarde,” they’ll tell me, which roughly translates into: “This is your punishment for EVERYTHING.”

Being a “right-brained creative” (as I like to brand myself to all who dare look inside my closet) has its perks when it comes to imagination, originality and big ideas, but it’s less useful when it comes to, say, budgeting for quarterly tax payments. There is no greater pain than budgeting for quarterly tax payments. It’s like layaway for rich people, except you aren’t rich (because, quarterly tax payments) and you don’t get to pick up a Kmart lawn mower at the end of it all. All you get to pick up are broken pieces of profits that once were.

But alas!

That doesn’t mean that the torture of it all exempts you from carrying out your Very Official Responsibilities As a Person in Business for Themselves. And in fact, there are five things that creative business people desperately need to get better at, as I have had to (hilariously, painfully, grievously) get better at myself.

So allow me to share five things that I am quickly approaching superstar status at, despite my humble beginnings:


  1. How the Freak to Budget for Your Business

    Jesus Crip Gang: there’s nothing worse than up and down revenue that ISN’T PREDICTABLE. And yet! And yet! Most of us still run around just crossing our fingers and betting on our abilities to “make it happen,” as we need it, on-demand. What a terrible plan this is (trust me, I know): it’s like closing your eyes and hoping that through sheer willpower, a freshly baked loaf of sourdough is going to replenish itself in your kitchen every week. Sourdough doesn’t happen unless you make it, and shockingly, money doesn’t, either. Which means that, you need to get a whole hell of a lot better at budgeting for your business so you can operate several months in advance of your expenses. And let me tell you what: You Need a Budget is CHANGING MY LIFE. My assistant, Elizabeth, became obsessed with the app for her personal finances, and after hearing her say it enough times, I thought I would check it out for mine. That’s when I realized I could use it for my business, too: and by golly, Gene! IT’S A FRIGGING MIRACLE. It’s like having an envelope system, but digitized: you set up “envelopes” for each expense and/or goal you have, such as your quarterly taxes, and then as money comes in you distribute it. Once those envelopes are filled, you take the remaining money you’ve got and distribute it among next month’s expenses. The software tells you how much you need to put in each monthly envelope in order to hit your goal by September, say, so you can make sure you’re saving a little bit at a time each month (instead of getting whooped by a sudden $30,000 tax bill.) Life. Changing.

  2. How the Freak to Pay Off Your Credit Cards The Smart Way

    You know, I was recently thunderstruck when I looked at the details of one of my credit card agreements, and saw 23% interest being charged. (The Tall Costa Rican says that I should be grateful: credit card interest in Costa Rica is more like 45%—GASP.) When I was a kid, AKA minutes ago, I used to look at interest as just a cost of doing business: I didn’t mind plopping something on a credit card if I knew it was a good investment (which includes investments in my quality of life, ahem). It was like pay-to-play for me, no different than paying to stay in someone’s Airbnb. But then I started getting interested in investing. And I realized that no where on the planet am I going to get a 23% return on my investment—which meant that no matter how well I invested, even in the stock market, any dollars I put on my credit card were effectively wiping out my gains. This might be common sense to you, but for someone who looked at credit cards as merely access to large sums of money when required, my thinking needed a big adjustment! So I took the money I was going to invest one month—including into my emergency fund—and instead, used all of it to wipe out any existing credit card balances. Now, I’m starting fresh knowing that the money I’m earning in my investments is actually money I’m earning—not earning “on the surface” but losing over there. So if you’ve got some debt hanging out over there, definitely read this article from Ellevest that teaches “The Avalanche Method” for paying it off. Hint: start with the credit card with the highest interest rate and murder it for a few months, while paying minimum payments on the rest—rinse and repeat. Then check out Ellevest, once you’ve paid off those credit cards, because I am in LOVE WITH THEIR INVESTING APP.

  3. How the Freak to Set Up a Nifty Little Retirement Plan Exclusively for Small Biz Owners

    My accountant and I were literally talking about this this morning, because I’m all balls-to-the-wall with traditional investing, but didn’t bother with, you know, AN “OFFICIAL” COMPANY RETIREMENT PLAN. (Even though I kinda sorta knew I needed to, grrrrrr.) So here’s the deal: there’s something called a SEP IRA that’s exclusively for business owners and and IS A TAX DEDUCTION FOR YOUR COMPANY. You can contribute up to 25% of your wages, which blows traditional IRAs out of the water, and then alllll the money isn’t taxed until you withdraw it at 59.5. (Unless you withdraw early, which you can do without penalty if you’re buying a house for the first time, need it for medical expenses, or you’re enrolling in higher education.) That’s kind of good if you imagine that right now you’re going to be making ALL the money now while you’re young—and therefore fall into higher tax bracket now than you will later. So you won’t pay taxes on that money now, you’ll pay on it later, when your tax bracket is lower because you’re making less money because you’re over it and ready to chill in your backyard with Better Homes & Garden. HOLLA. Read about SEP IRAs over hurrrrrrr.

  4. How the Freak to Know What You Can Afford to Invest in the First Place

    If you’re like, this all sounds great but I have no real handle on what I’m actually earning after expenses and it’s all so volatile and unpredictable and who am I and what’s the president’s name?! (Never mind, don’t answer that.) Then darling, you NEED to have someone categorizing your transactions and you NEED it to be done by my favorite company on earth, Bench. They connect to your bank account and all of your transactions flow in automatically, and then you’ve got a real bookkeeper behind the scenes who’s manually categorizing everything and making your money super user-friendly. Which means? You can finally know how much actual profit you have, versus your costs (especially those hidden ones) and at tax time (which is now), all you have to do is click a button and voilà! Submitted! No more searching around for receipts and having no idea where to start with your taxes. It’s. All. Done. For. You. Bench is literally my superhero and no I will not stop talking about them. (Especially when their team was so cute and bought my book for the office!)

  5. How the Freak to Grow Your Team and Pay Your People (Especially if You’re an S-Corp)

    If you’re like, man, I really want to hire people and/or bring on contractors buttttt….isn’t that complicated? You need Gusto. Holy stinky doodles, do you need Gusto. This software is LIFE—especially for someone like me who is registered as an S-Corp, which means that I am an employee of my own company (and I need to get paid like an employee, AKA using regular payroll and tax deductions). So I’m using Gusto to process my payroll, and I can also pay contractors with it as well. In addition, you can set up all sorts of benefits for your people right inside, from setting vacation time and sick leave, to even letting them borrow money from their next paycheck to help fill in gaps in between pay cycles…all of which they can do through the app. Cool, huh? Gusto is saving my sanity day after day, and you definitely needed to know about it.

  6. And Finally—Bonus Round!—How the Freak to Make a Will and Trust for Your Business

    Because, hi, you have assets now. You own a business. (That’s worth something!) And you have bank accounts. And you might own property. And you might have a life insurance policy. And you might want to dictate what happens if you’re brain dead on a gurney. And alllllll of that needs to, you know, come with instructions. Most of us know they should probably have a will, but most of us don’t do it because it seems like this hugely complicated process involving lawyers and documents and blahblity blah blah blah, right? Enter: Trust & Will. I’m pretty obsessed with them. If nothing but a business exercise, take a look at their site and see how they’re disrupting the death industry in the BEST way.

So, listen, if you want me to throw you a birthday party, I might not be the best candidate. Then again, maybe all I need is an app. It’ll be called “How to be a Good Fucking Friend,” and not only will it automatically plan birthdays for you, it’ll also auto-answer your telephone and respond to texts before three days have gone by and you’re still sitting on the computer in your soiled pajamas, totally engrossed in another article by the New York Times, stopping only to pee and buy forty-nine boxes of cherry-flavored condoms. The ush.



Unpopular Ideas for Living a Happier Life.

More Posts from: