The productivity mindset that tripled my revenue

Note: This is a guest post by Chris Guillebeau excerpted from his new book Side Hustle: From Idea to Income in 27 Days. We’ll be interviewing Chris about his new book live on our Facebook page on Oct. 5th at 8 p.m. ET. Get a reminder here (iCal)(Google)(Outlook).

Serial hustler Adam White had several projects competing for his attention. There was the day job as director of digital marketing for a charter bus company. There was the film he was making at night and on weekends, and the young adult novel he tried to make progress on each morning before leaving for the office. Busy people are good at side hustles, because they know how to make their time count.

As part of his day job, he spent a lot of time doing promotion through guest posts on business blogs. The process was time-consuming, and he had a hard time keeping up with them all. Some blogs accepted guest posts and others didn’t. The ones that did usually had certain requirements that had to be followed, which weren’t always consistent. Then, after submitting a post, Adam had to remember to follow up if he didn’t hear back within a reasonable period of time. Procedurally, it was a bit of a nightmare.

He started to compile detailed notes on all the blogs that accepted posts, as well as a system to track his submissions (remember the classic side hustle lesson: if what you need doesn’t exist, make it yourself). Before he knew it, he had a database of information on hundreds of blogs covering lots of different categories. Thus was born the idea: Why not offer his “Guest Post Tracker” to other writers with the same problem?

After putting together a simple sales page, he asked a friend to write about it in an online business forum. Right away, more than ten people signed up, paying a $49 fee. Before the end of the week, another ten payments had come through. Adam had another side project! The interesting thing about this hustle is that it essentially promotes itself. To market it, Adam simply writes short guest posts … about guest posts. Each one typically brings in another batch of customers right away, as well as an ongoing stream of customers who find the post over time.

Ninety days in, Guest Post Tracker was bringing in $1,000 a month. By further systematizing the process and repeatedly testing to improve conversion using A/B testing, it was soon up to $2,000 a month. Six weeks after we first talked, Adam wrote me back to say this kind of process work had helped even more: the site was now up to $3,000 a month.

The biggest challenge for Adam, as for many hustlers, is time. With the digital marketing job, the film he’s making, and the novel he’s writing, the guest post hustle takes a backseat to each of those commitments. Still, because his Guest Post Tracker saves him so much time at his day job, he’s able to find time to work on selling that gift of time to others.

Write down everything you do

Adam’s hustle worked because it was a great idea, but he made it work a lot better when he applied a systems-based, process-driven approach to it. When it comes to hustling, “systems” doesn’t mean fancy IT software or expensive network servers; it simply refers to all the procedures that allow you to serve customers or otherwise make money.

At some point in their journey, longtime hustlers learn an important lesson: You can do something repeatedly, or you can do something just once. They also usually find out that documenting your work does not come naturally. Frankly, most people don’t want to do it—it’s a future pain point, so they wait until they have to. But if you ever want to grow your hustle, or if you just want to save time, consider doing it on the front end instead. Documenting your processes gets you out of the mundane details of the day to day. It keeps you from management by inbox. It makes life easier, and it also tends to make you more money.

Make workflows for your repeat systems

Recall that a workflow is any sequence of processes that shows exactly what needs to happen for any particular outcome. You learned to list out every step that needs to happen to develop an idea. These workflows, in contrast, are for existing operations. They can help you iron out problems, improve efficiency, and make it much easier to outsource or get some help on parts of your hustle as it grows or as you expand it into other things.

The two most important workflows for most hustles are sales and service. Basically, you want to document how you sell to people and how they receive what they purchase.

Adam’s sales workflow was pretty simple. He’d built a basic website that described the guest post tracking service, and he made two versions of the checkout page to test which one would convert better. To bring people to the site, he wrote guest posts on different blogs. He also pitched the product to other business media for coverage. That was pretty much it—no fancy marketing strategy, no employees, and extremely low expenses. It looked like this:GL Flow 1

His service workflow was also simple. All he had to do was make sure that buyers received access to the tracking program, that it worked, and that it was updated fairly regularly to reflect new blogs and changes in policy. There was an occasional customer service inquiry or refund request to attend to, but all that took very little time. The process looked like this:GL Flow 2

Adam doesn’t need my advice, but let’s say he decided to create a different version of the Guest Post Tracker. The existing version is a product. People pay once for it and receive access to something he’s made that contains a lot of information. Most likely, some of that information is relevant to them and some of it isn’t. Now let’s say the new, different version of the Guest Post Tracker that Adam decides to make is a service. You can still buy the basic version for $49, but if you want a customized version, complete with a one-hour advisory call from Adam, you can buy that for $199.

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This upgraded version of the hustle requires a new service workflow, since he now has to create customized trackers, schedule calls, and deliver advice to customers. It’s still fairly simple, but notice the new workflow elements:GL Flow 3

For workflows like this, where you need to schedule calls or other meetings with customers, it’s especially important to be clear on all the details. Consider this an example of a sub-workflow that focuses on something even more specific, like scheduling:

  • How will the calls be scheduled?
  • When will the calls be scheduled?
  • What will be the frequency of the calls—just once, more than once, or whenever the customer needs?
  • What will be the agenda of the calls?
  • What kind of prep work will you need to do before the call?
  • What kind of follow-up work will you need to do after the call?

If this sounds tedious, remember that if something is broken in even one small part of your workflow, your hustle may falter in any number of ways. Your customers may become frustrated, your potential customers may not be persuaded to purchase, and you may struggle with keeping up. Taking the time to document your systems and improve your workflows will almost always be less tedious than the damage control you’ll have to do if things go awry.


Another important workflow is focused entirely on welcoming and orienting new customers. This is called onboarding, and it’s all about helping your buyers become familiar with whatever they’ve just paid for. As with the service workflow, setting up a proper onboarding process helps prevent frustration, both yours and theirs. Your goal is to create a happy, reassuring journey for your customer— and help them experience the best of what your hustle has to offer. Better onboarding creates increased retention, repeat business, and referrals.

Onboarding can be done in a number of ways. One of the simplest and most common is through an email sequence that customers receive upon signing up. When you purchase something online, you’ll almost always receive a confirmation message with a receipt. But much of the time, it doesn’t end there. Over the next few days or weeks, you’ll usually receive an additional series of messages designed to help you become familiar with the product or service and answer any questions you may have.

There are many different formats for an onboarding email series. Yours could look something like this:

  • Message #1, sent right after purchase: “Welcome, new customer!”
  • Message #2, sent the next day: “Watch this video to learn the most important elements of your new service.”
  • Message #3, sent three days later: “These advanced features will make your life easier.”
  • Message #4, sent a week later: “Hey, just checking in. Is everything working for you, and do you have any questions?”

Of course, your onboarding series will differ depending on the nature or complexity of your product or service, with some requiring more detail and guidance than others. In general, though, remember that your primary goal is to make the process as pleasant and seamless for the customer as possible.

Tools to improve your system

Hustles that turn into thriving small businesses eventually need a few specific tools. You may not need all these things in the beginning—remember, simple is best when you’re starting out— but it’s good to familiarize yourself with what they are, so that you’ll know what to look for when the time comes.

Contact management

Commonly known as CRM, for customer relationship management, this software helps you keep tabs on lots of different people. It’s particularly important if you sell expensive items or services to specific contacts you build a relationship with over time. It’s less important if you sell a lot of items or services to anyone who wants them.

Examples: Hubspot, Salesforce

Project management

If you end up working with a designer, web developer, assistant, or anyone else, it’s great to have a shared, online workspace where you can monitor the status of different tasks.

Examples: Trello, Asana, Basecamp


At first, you’ll probably do this yourself—but whether you end up getting help or just continue on the DIY model, you’ll need to track expenses and income. You can get by with a simple spreadsheet, but when the time comes to prepare your taxes, software makes it much easier.

Examples: Wave Accounting, FreshBooks, QuickBooks

Password recorder

We all know that you shouldn’t use the same password more than once, or at least not for everything, but these days you practically need a login to turn the coffee maker on in the morning. How do you keep up with so many passwords? The simple answer is: you don’t. You register with a system that generates secure passwords and stores them for you so you don’t have to remember them.

Examples: LastPass, RoboForm, Dashlane ***

Adam White, the serial hustler, had correctly identified a need for a system to help him compile information on all the different blogs he was pitching. He then used his hustle skills to make a quick profit from it. The real success, however, came when he applied his skill in systemizing and A/B testing to streamline his workflows. $3,000 a month is a lot more than $1,000 a month — and the difference came entirely by working smart, not just hard. Now he just needed to write that YA novel.

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