25 Productivity and Automation Hacks from a 6-Figure Freelancer

This contribution comes from Paul Maplesden, a friendly, professional freelance writer on Fiverr Pro. He specializes in business, technology, software, and finance and lives in the beautiful mountains of Western NC.

He loves the challenge of taking complex subjects and breaking them down so they are easy to understand. He likes hats, dogs, tea, and “The Princess Bride.”

Inconceivable!

Take it away, Paul!

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Greetings fellow hustlers, I have a small confession to make. For me, the hustle isn’t just a side gig — it’s what I do all day, every day (with some time off for good behavior on weekends!).

I’m a freelance writer, and if there’s one thing I’ve learned from the hustle, it’s that you have to make the most of every minute in your day.

I should know — this year I will:

• write more than 600,000 words
• work with over 200 clients
• complete 700 articles
• and invoice over $100,000.

I need to make sure I’m using my time as effectively as possible, and I want to share exactly how I do that.

There’s a great deal written about how to find work in the first place, but once you have it, how do you manage everything effectively? You must avoid becoming a victim of your own success, keep your work-life balance healthy, delight your clients, and ensure you still have enough projects coming in.

Nick’s Notes: It’s a serious juggling act!

If you want to work in harmony and avoid the anxiety monster, you need to look at every aspect of your work and ask “How can I make this better?”

I’m a productivity geek, so I’ve spent a lot of time tweaking and refining the approach and methods I use to get the most out of my working life. This post is partly inspired by my work on Fiverr Pro — a platform that’s built around optimizing time and services.

Nick’s Notes: As you know, Fiverr is one of my favorite “Buy Button” platforms for beginning freelancers and side hustlers.

Here are my secrets.

First, Understand What Your Side Hustle Involves

The first step is an understanding and acceptance of what your business really involves. The life of a freelancer, or anyone running their own side hustle, is split into four main parts:

1. Looking for work
2. Dealing with clients
3. Handling the administration
4. Doing the actual work

Sound about right?

Looking for Work

There are lots of ways to find work — job boards, social media, referrals, and more. This is one of the greatest issues for a freelancer or side hustler — the tension between looking for work, finding it, and the pipeline of work you currently have planned.

Dealing with Clients

Once you have work, you can spend lots of time negotiating rates, getting contracts in place, dealing with emails and communications, taking payments, and making revisions. It’s essential though — freelancers and side hustlers live or die on reputation and customer service, so it’s vital to make everything accessible, friendly, and transparent.

Handling the Administration

This is probably the biggest time-suck of all for any hustler! It’s a silent productivity killer — we’re talking about raising invoices, tracking expenses, managing finances, doing marketing, filing taxes, and all the other tiny tasks that fill up the day.

Doing Chargeable Work

Finally, we get to the area where we all want to be. Whether it’s creating an eBook, selling an online course, working as a freelancer, managing an eCommerce store, or something else, this is how we actually make our money.

Next, Manage the Tension Between What You Have to Do, and What You Want to Do!

The less time we spend on the first three areas, the more time we can spend on the last one. We have to get the balance right — we can’t ignore looking for work, managing clients, or doing our admin, but what we can do is make that easier and more efficient.

It’s a case of lots of small changes adding up to more chargeable hours in the day.

If we want to make our work as effective as possible, we need to optimize, automate, and improve the methods we use.

Finally, Automate and Optimize (for People Who Aren’t Productivity Geeks)

I know I’m a bit weird when it comes to productivity. There aren’t many people out there who enjoy talking about the most effective way to use spreadsheets, or the optimal task management integrations.

Fear not! Even if you don’t know your pivot table from your Pomodoro timer, I’ve got you covered.

Nick’s Notes: Come on, people, that was funny!

Automation and optimization is just about using tools to work in a more effective way. The main way I achieve this is by getting the various pieces of software I use every day to communicate with each other.

For example, I can get an email notification every time a new job is posted that meets my criteria, or I can automatically copy a project from my time tracking app into my accounting software. This is known as “integration.”

There are a few different ways to do this — many applications have integrations built in. For those that don’t, there are a couple of awesome services called If This Then That and Zapier. Both are free to use at a basic level, and we’ll be taking advantage of that.

Nick’s Notes: Love me some IFTTT! Among the “applets” I have set up:

• Whenever I make a new blog post, add it to my Buffer.
• Whenever a file hits a certain Dropbox folder, notify my virtual assistant.
• Whenever I get an email with a specific subject line, notify my virtual assistant service.

It’s time to roll up our sleeves and get to work. For each of the four areas above I’m going to give you some hints, tips, methods, and approaches to automate and optimize your time.

How to Use These Side Hustle Optimization Tips

I’ve presented these tips as a light buffet of delicious techniques. Take them on, one at a time. There’s no “best approach” or “one size fits all” method. If you like something, keep it and refine it. If you don’t, kill it with fire!

Let’s get into it.

Tools and Techniques for Optimizing How You Find Work

We’re going to create easy ways to get automatically notified when works comes up that you might be interested in applying for or getting involved with.

1. Create an Email Folder and Rules to Store Your Work Notifications

The easiest way to get notified is via email, but you don’t want all these messages clogging up your inbox. Get around this by creating a specific folder in your email software to hold all your job notifications.

Then, set up rules to automatically move your notifications to that folder. This is built into software like Outlook or Gmail, and you can use the sender or the subject line to identify job notifications and move them.

I’ll share how to actually get those job notification emails below.

Nick’s Notes: Here’s a quick video I made that shows how to create a folder in Gmail and how you might automatically direct incoming notifications to that folder.

Work Out the Side Hustle Keywords You’re Looking For

Next, choose the search terms you’d normally use when finding work. For example if you’re a freelance designer it might be business card design, brochure design, flyer design, etc.

If you’re writing an eBook on dropshipping, you’d look for articles and forums on dropshipping where you can share your work. You will probably want between 12 and 20 keywords.

2. Set Up Google Alerts for Your Side Hustle Keywords

Google Alerts is the easiest way to stay on top of your industry as articles and jobs get published online.

Create alerts for each of your terms, then when something appears you’ll get an alert directly to your email and can follow up. You can choose if you want to be notified of all results or just the best ones, and can receive updates as they appear, or just once a day.

3. Monitor Social Media for Keywords

Some hustlers find work through social media, and that’s something else you can automate. This post on Hootsuite links to several tools that can help you track keywords across Facebook, Twitter, Instagram, Pinterest, LinkedIn, and more.

Social media moves fast, so you will likely want to keep a close eye on mentions of the topics you’re interested in.

4. Get Emails from Job Boards when New Jobs are Posted via RSS

There are probably dozens of job boards relating to your niche, and visiting all of them, every day, is incredibly time consuming. Instead, in most cases, you can automatically get notifications from job boards when new jobs are posted, then visit and apply to the ones you’re interested in.

You do this using the “RSS Feed” of a job board, and getting the service “If This Then That” to send you an email whenever new jobs are posted. Here’s how to set it up.

First, make a list of job boards in your side hustle niche. Here are some places to get started:

• The Simply Career Job Board Directory
• Good and Co Career Insights
• VetJobs Niche Job Board Websites.
• Broadbean Job Board Search

Go to each job board you want to get notifications from and search for its “RSS Feed” — there might be a link like “Subscribe via RSS.”

Register with If This Then That and use this applet.

Fill in all the details, and each time a job is posted, you’ll get a notification in your email — brilliant!

This doesn’t just work with job boards — it works with anything that has an RSS feed — blogs, forums, discussion groups, subreddits. For example, I have it setup so that whenever a post is made in the “hire a writer” subreddit, I get notified.

5. Sign Up for Job Alert Emails

There are plenty of places online that post jobs and then notify you via email — without you having to set up your own RSS notification system.

Whether those are specialist job boards or alerts from the big portals like Indeed or Monster, you can get regular updates on new opportunities. Again, this is all about saving you time on the “looking for work” phase of your hustle.

Refine Your Rules and Review Your Opportunities

Once you have all these notifications coming in, make sure you review your email rules on a regular basis. You can make tweaks to the rules themselves and the keywords and tools that trigger emails.

You will want to tweak and refine until you get the right balance of job opportunities.

Once you’ve done that, review your job folder on a regular basis (I look at mine twice a day). You can quickly identify the opportunities you want to review and get hustling!

Tools and Techniques for Dealing with Clients

One of the things I love about working with Fiverr is how easy they make it to manage client relationships, and it’s something you can apply wherever you work.

6. Create a Separate Email Folder for Each Client

When you’re working with dozens of clients, it’s vital to keep track of your conversations with each one.

I recommend creating a separate folder for each client you’re working with, and moving emails into those folders once you’ve read and responded to the client.

I have client folders under an “active” master folder if I’m still working with them, and a “Dormant” one for previous clients.

7. Create Templates for Common Messages

There are certain messages you’ll send to clients again and again. These might be thing like updates on how their work is going, requests for information, contract cover letters, and more.

Learn the similar types of messages you send again and again, and create templates for them. That way, you can just select the email from a list and it will automatically populate in your email client. Here’s how to set them up in Gmail and Outlook.

Nick’s Notes: If you don’t like the Canned Responses tool built-in to Gmail, you can try something like Text Expander for Chrome and build your own keyboard shortcuts for commonly-used phrases and emails.

8. Create Template Documents

Just like your email, there will be documents you use again and again. These might be contracts, requirements gathering forms, briefing notes, and the like. Start out by creating template documents with all the key information, then leave sections where you can insert specific data later on.

Here’s a guide I wrote on creating a good freelance contract that serves as a helpful basis for such a document.

If you want to get important documents signed, use a document signing service. The best one I have found is RightSignature.

Nick’s Notes: Down the road, you may even be able to sell your template as a standalone product, like Kendell Rizzo ended up doing in her crowdfunding copywriting business.

9. Create a Frequently Asked Questions Guide for Clients

Clients will have questions they ask again and again. Make a note of the most common questions you get, then create a “Frequently Asked Questions” section on your website to answer them, and direct clients to those answers.

10. Optimize Your Requirements Gathering

One of the big time sinks for freelancers and hustlers is the time you spend understanding what your client needs. You probably ask exactly the same questions each time, too.

Well, you can automate that.

It’s easy to create a form on your website that asks all of the questions you need answered to do your work. You can then send the client to that page, get them to submit the answers, then have them automatically sent to you.

Nick’s Notes: I normally use Google Forms to collect information but several people I know have the data collection part of their business built-into their calendar booking tool like ScheduleOnce or Calendly.

11. Make Payments Easy

We spend so much time chasing up payments from clients!

You can make that whole process easier by integrating payments into your invoices. Online services like PayPal or Stripe make it easy to raise invoices for custom amounts and send them directly to clients so they can easily pay online.

Nick’s Notes: Freshbooks is a long-time sponsor of The Side Hustle Show and does this as well. In PayPal though, one of my favorite features is the subscription option. It saves you the time and trouble of having to re-bill the client every month — it just happens automatically!

12. Let Clients See Your Calendar

Sometimes, clients will want to know your availability (it’s a question I get pretty much every day).

If you use an online calendar you’ll often have the choice to embed it in your website and show when you’re free. The level of detail you show is up to you — it can display individual appointments, or simply blocks of free and busy time.

Nick’s Notes: I’ve been using ScheduleOnce for years and love it. As part of my “theme-day” experiment this year, Tuesdays are the only days that show any availability for booking.

13. Proactively Communicate with Clients (with email templates)

Apart from delivering awesome work, the one thing that will improve client satisfaction above all else is “proactive communication.”

This is really just a fancy way of saying you need to contact your client before they contact you. I normally make a point of contacting my client at the following points in a project:

• To let them know I have received a request for work or order.
• To get briefing information and requirements from them.
• To let them know I am starting on their work.
• When I deliver the work.
• A follow-up a couple of days later.

Nick’s Notes: When I worked in the car business, this was the golden rule for service advisors: call your customers before they call you.

This works really well for managing expectations, and you can easily set up email templates for all of these areas. Create a simple routine and habit of dropping a quick email to a client on your terms and it will make your communications more efficient and your customers happier.

14. Follow Up with Clients on a Regular Basis

Something else I do is to check up with clients once every couple of months.

I write to confirm they are happy with my work and if there’s anything they would like to change. The responses to these emails is almost unanimously positive, and is a great way to show you’re putting their needs first.

Nick’s Notes: This is super smart because it keeps Paul top-of-mind for his clients. You can use a tool like Nudgemail to set these reminders up in the future, or add a calendar event via IFTTT triggered by your “final delivery” email template subject line.

Tools and Techniques for Handling Administration

This is one of the toughest areas to optimize, as the way individual hustlers and freelancers work varies so much. That said, here are a few good tips for optimizing all the admin you need to do.

15. Note Down ALL of Your Administrative Tasks

Admin varies so much from business to business. Make a note of anything you do that is not either looking for work, managing clients, or doing chargeable work — that right there is your administration overhead. Typical examples include:

• Accounting and finances like expenses and invoices.
• Payroll and drawings.
• Marketing, advertising, and promotions.
• Social media communications for work.
• Managing office supplies, software, stationery, and sundries.
• Reordering stock and inventory items.
• Recording, filing, and paying your taxes.
• Customer service.
• Doing paperwork.
• Scheduling meetings.
• Dealing with suppliers, vendors, and partners.
• Keeping your website and portfolio up-to-date.

Get into the weeds on this one — note down everything you have to do on a regular basis. It will help you remember to do it going forward.

Nick’s Notes: You might consider the time tracking experiment to help itemize out the tasks and how much time they take.

16. Dedicate One Day a Week for Admin Tasks

One of the main issues with having to complete lots of small tasks is the time spent shifting focus between actions.

If at all possible, try to put all your admin tasks into one part of one day. Put aside a morning or afternoon when that’s all you’re going to focus on.

That means less mental shifting for you, so you can chunk through all those admin tasks nice and quickly so you can get back to paying work.

Nick’s Notes: For me under my new “theme day” system, Wednesday afternoon is admin time.

17. Get a Decent To Do List or Task Manager

One of the main issues with having so much to do is keeping track of it all.

If we’re tracking things in multiple places that causes a lot of tiredness and anxiety — what if we forget a critical task? That’s why I am a huge advocate of to-do managers and task lists.

I have tried *all* of the main ones out there. For most hustlers and freelancers, when you’re mostly working by yourself and need something quick and simple, you do not need full-blown project management software. Instead, an app like Trello, Todoist, Any.do, Producteev, or Wunderlist will meet pretty much all of your needs.

The app you choose depends on your personal preferences — all of them have a free version, so try them out and see what works for you. I really like Trello and Todoist, but tastes do vary enormously.

Nick’s Notes: My approach of Google Calendar + pen and paper might be due for an upgrade.

18. Add All Your Admin Tasks as Recurring Actions

Once you know everything you need to do, add it to you task manager. Be sure to create recurring or repeating tasks for regular admin activities. Then, you’ll automatically be notified when anything important needs to happen.

Nick’s Notes: One way I’ve applied this was with a recurring Calendar event. To make an event recurring in Google Calendar, just hit the “Repeat” button:

I have recurring events for administrative tasks like welcoming students to my Udemy course, cleaning up my email list, running certain reports, and even giving the side hustle shih tzu his medicine.

19. Get a Decent Productivity System in Place

If you really want to be a productivity ninja (that’s a guy in dark pajamas with a stopwatch and a tick-list), you should look at using a proper productivity framework.

There are plenty out there — Getting Things Done, Pomodoro, Kanban, and more. Need help choosing? Here’s another handy guide I wrote.

Nick’s Notes: John Lee Dumas shared the effectiveness of his modified Pomodoro system in an episode of the podcast about mastering productivity, discipline, and focus.

20. Get a Decent Accounting System in Place

The one area that’s likely to take up most of your admin time is accounting.

Whether it’s raising invoices, tracking expenses, making sure clients pay, doing payroll, or tracking finances, money management is a huge overhead. Fortunately, there are lots of great online options for managing your business finances including FreshBooks, QuickBooks, Wave Accounting, and many more.

Pick one. Use it. Love it.

21. Delegate Administrative Work

A good way to optimize though is to look at your list of administrative tasks and Google ways to make each task more efficient and integrate everything together. You might be surprised by what’s out there and what people have come up with.

When you’ve reached the limits of automation, the next phase is delegation. Could you find a virtual assistant or specialist to help support a certain area of your business? Fiverr is a good place to start your search.

Tools and Techniques for Optimizing Chargeable Work

By this point you’ve honed your focus and shaved hours of wasted time each week. You’ve optimized, automated, and integrated — and you might think you’re done — but not so fast, my friend!

There are also ways to optimize the chargeable work that you do.

21. Track Your Work as Soon as it Comes In

Every piece of chargeable work you have needs to go into your to do list manager. As soon as you’ve confirmed deadlines with the client, add it to your task list and make sure you complete it ahead of time.

In most cases you can automate this through Zapier or IFTTT.

22. Create a Schedule and Stick to It

If you have lots of work, the chances are your calendar is very full.

Review your schedule on a regular basis and block out enough time to get everything done. Remember to also plan in time for administration, looking for work, and client communications. Review your tasks on a daily basis and prioritize chargeable work.

Nick’s Notes: Seriously. Put it on the calendar or it won’t get done.

23. Use One Platform for Creative Work

You don’t want to have to work across multiple platforms. Choose tools that you like working with, and stick to them.

As a writer I work almost exclusively in Google Docs — if you’re a designer, illustrator, or other creative, you likely have favorite tools too. Learn them, use them, love them. Bonus points if the platform you use allows for easy collaboration and revisions with clients.

24. Make it Easy to Track and Find Work

Create a sensible naming and folder system for tracking the work you’re doing.

You don’t want to have to search through 475 files to find the right version of the right project for the right client. Come up with a naming convention that works for you and make sure you use it.

My typical system is: client name – project name – version number. This also makes it much easier to search your files later when you’re looking for previous work.

Nick’s Notes: When I started outsourcing some of my podcast editing, the company I hired requested I use a similar (and consistent) naming convention for all the audio files. I hadn’t really considered it before but it must make their life significantly easier!

25. Time All Your Tasks

One of the best ways to make use of your time is to track where it goes.

You need to make time tracking as easy as possible though. My recommendation for time tracking is Toggl — it’s free and integrates with pretty much everything.

I copy all of my Toggl entries into a Google sheet (using Zapier) so I can then analyze the work I am doing for every client.

For example, as of right now, this Side Hustle Nation blog post has taken five hours and eight minutes, so it’s probably about time to wrap it up.

Nick’s Notes: Wow, thanks for investing that kind of time in this post! It shows! In my conversation with the super disciplined author Steve Scott, he recommended the time tracking tool aTimeLogger, so there’s another one to check out.

When I go through my spurts of time-tracking, I typically use Toggl or just log the projects in Excel.

In Closing

And that’s it! 4,000 words of deliciousness on how to optimize the way you work to squeeze the most out of every minute.

I hope you’ve found some useful hints and tips in here, but don’t be a stranger! Drop us a note in the comments on your favorite ways to optimize time, and the methods you use to run your successful side hustles.

And, if you’re looking for a friendly writer for any business, finance, technology, or software topics, you know where to find me!

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