Secrets of the 3 day work week

Can anyone (“anyone” meaning real, live folks with regular jobs) actually afford to work just three days per week?

Surprisingly, the simple answer is: Yes.

Believe it or not, people roam this earth who thrive on part-time work, pay all their bills, and continue to avoid an untimely death from Ramen-related scurvy. Even better, three of them have agreed to spill their self-employment secrets to help you put your Freedom Friday plans into motion.

 Who are these magicians? Meet Nita Baum, the founder of b*Free and a former consultant for the Chicago public school system, Kean Keeks, a property manager and the founder of LiveDiff, and ‘The Consultant,’ a startup professional who chose to remain anonymous (but wanted to give the Trello readers some great tips, anyways).

This is the story of how they’ve hacked their life to get more work done in less time, and how you too can start to reduce your workload without compromising your paycheck.

Part-Time Professions

Before you enter into this alluring world, do note: The biggest (and most common) step to take towards full-time reward for part-time effort is self-employment. You might be hard-pressed to find an employer who’s willing to pay you for more hours than you put in, but when you offer a service as a consultant, you can factor your expertise, connections, and more into your fees.

This isn’t to mention opportunities for “passive income,” which you can earn, for example, by selling products online that deliver you a return separate of your time spent earning income. Always carefully consider the pros and cons of becoming your own boss when assessing your professional and financial future.

So exactly what kinds of professions allow people to reduce their hours spent in the office? For these seasoned three-day weekers, the opportunities are as creative as their outlook on work-life balance. For instance, Kean Keek’s property management expertise expands beyond his company:

“I rent my own Airbnbs and help facilitate other Airbnbs. It averages three days a week or less, but it’s seasonal. During the heavier seasons, like tour seasons, I might work four days a week. And then it’s a whole season where I’m working one day a week.”

Nita Baum’s current work as a freelance business consultant spun out of her previous full-time roles:

“I was a strategy and organizational change consultant in Chicago. That included policy work. For example, I would plan the five-year strategy for improving education in a Chicago school district. I led that process and helped navigate the politics of managing a board of directors. I also built buy-in for the strategy and guided people through the initial stages of putting it into action.”

The Consultant expanded on the core function of his previous roles as well, looking at how to hone in on exactly what made him effective as an expert in his field:

“I previously had the title of Chief Technology Officer, but I kind of describe myself as the CEO’s right-hand man—like the Hamilton reference. I help keep the interests of developers and the customers aligned with the CEO. I use my experience from the startup world and help guide the company along. You could call me a mediator.”

Making The Leap To Fewer Work Days

Speaking with each professional, one shared truth is clear: a schedule this sweet doesn’t happen overnight. It takes a lot of negotiation, trust-building, and the kind of financial planning that allows a person to walk away from a deal that doesn’t offer the right return.

For Nita, getting to a 3 day work week required building her skill sets and relationships over time with this goal in mind. For example, she already had a solid relationship with the person who promoted her into her new role. That meant that he trusted her enough to give her the reins over her workweek. Plus, since Nita had a deep understanding of the standard rates in her industry, she was equipped to effectively negotiate for herself:

“I managed my own schedule as a consultant, so I had the ability to reduce my work days, although making it happen is another type of effort. To do that, I negotiated on the price of my contracts in such a way that it allowed me to be able to live off of them effectively without having to work full weeks for the entire year.

I did that by learning about the available funding sources for projects that I was working on. That way, I had a sense of what was reasonable to ask for. I made it a practice to learn about the financial situations of my clients. That made me better equipped to negotiate.”

When your bank account is low, it’s easy to let negotiation fly out the window. That’s why careful planning around income versus expenses is key to confidently asking for what you want in the workplace. This approach helped The Consultant land the type of job that he wanted:

“I already had a nice amount of savings, and I had other inbound interest. So I was really comfortable negotiating a rate that would free up my schedule.”

Knowing what number will afford you the lifestyle you want is necessary when sourcing opportunities, he notes: “I knew that I wanted only one paying client, and I wanted to be on retainer. So, to negotiate, I pretty much took my salary from my last job, combined it with the value of the equity I had, and cut it in half.”

Work-Life Balance: Lessons Learned

Beyond financial matters, making the leap to a three day workweek also needs some personal development and planning. When it comes to learning how to pick the right opportunities, staying disciplined with your time, and finding a work-life balance, the struggle is real. Says Kean:

“I underestimated my tendency to be undisciplined in how I work. When I was working full-time, I didn’t realize that I was making that trade-off between hours in a chair and hours being actually productive. That nine hours a day is spent almost turned off. I was turning off a disciplined mind and being told what to do.”

When you go from being micromanaged to doing everything on your own, figuring out how to arrange your day–– and stick to the plan––can be a challenge. That’s exactly what he ran up against when he started creating his own calendar:

“It was tough. It’s still a unique challenge. When I was working full-time in a larger structure, there was someone there whose job it was to manage that structure for me. So my first year was about learning to effectively manage my time. There’s a shift. And not an easy one, but fortunately, it didn’t punish me financially. I lost some time and maybe some missed opportunities.”

For Kean, a small tweak to his time management made a world of difference. He learned to create systems for himself, so that he didn’t waste time thinking about how he was going to schedule his day:

“I’m more intentional about structures. I wasn’t using a calendar in my personal life before leaving my job. I never would have scheduled gym time or writing time, but I think it’s equally important to schedule them now. Instead of just systematizing my work, or creating systems around my work, I’m creating systems around my life. It sounds like it should be boring, or it’s not fun, but it’s crucial. And it can be fun. It’s just habit building.”

The biggest reason to create a system? Because time has more value when you have less of it, concludes Kean:

“I gained self-discipline when I had to focus more intensely on what I should do with my time and how I should structure it. Now that I’m self-employed, I’m constantly thinking, ‘What’s the most effective thing I can do right now? What will 10x my efforts in this?’”

Nita faced an additional problem. When she made the transition to the solopreneur lifestyle, she suddenly had to come to grips with having full control over her time––and her identity:

“I had been so used to identifying myself relative to an institution that I was part of. It was like I go to this school, or I work this company, and then when I was out of paradigm, I was like … who am I? And what do I do? It was very jarring in the beginning. It was the most difficult part, but also the greatest opportunity. I was like, ‘Oh, I have to answer this question. I have to figure out who I am.’”

She decided to bring spirituality and creativity into her time management process, developing a technique to curate her day that felt productive and maintainable:

“I actually designed a very specific process that I called ‘curating my inspiration.’ At that time, I didn’t know what I wanted to do. I said, ‘I don’t have an outcome in mind, because that feels like it’s going to narrow the possibilities of what I can create.’

So I only listened deeply to the things that resonated with me. I only consumed things that felt like they really resonated with my truths. I got really specific. I said I’m not eating food, I’m not watching movies, television, or any kind of media if it doesn’t deeply connect with me. And that led to the founding of b*Free, which basically is me and will be me for the rest of my life.”

Knowing your worth is a huge part of getting that balance right. Understand the unique value that you provide, and let that guide you to the types of clients and contracts you truly want. And when they find you, make your value and intentions clear, explains The Consultant, in order to achieve your ideal result:

“Have inbound interest. If someone comes to you and says they want to do something, you have the upper hand in the negotiation. And, as long as you have negotiation power, you can ask for the rate you want to be paid. You can negotiate for remote work. You can request whatever you (reasonably) want.”

But how do you reach that point where people are coming to you for your services? Professional networking, both online and offline, is a great place to start: “To gain that interest, you need to do interesting work and put it out there where people can find it. Work on your brand to a point where people know you for being good, and start building that pipeline of interest.”

The 3-Day Workweek Toolkit

The “three day a week” workers recommended a ton of resources, tools, and tips for building awesome work-life balance. Start hacking your workweek with this handy list:

Time-Saving Tools

  • Boomerang: Don’t waste time trying to remember which emails you were supposed to follow up with, and when. Boomerang them instead! This handy tool allows you to have an email return to your inbox whenever you want. Plus, you can schedule emails to be sent at a different time. (You know, in case you don’t want people to know that you’re responding to their email at 3 AM on a Tuesday.)
  • Trello: You need a productivity planner, workload manager, and collaboration tool that you can access anywhere, anytime, and Trello fits the bill. And at the low price of free, it’s a great home base for any budding solopreneur.
  • Grammarly: Communication with potential clients is at the core of setting up great relationships (and contracts), so avoid poor grammar or unclear sentences with your very own editor.
  • Anyone can have their own personal assistant thanks to artificial intelligence. Amy and Andrew are process-happy bots who will help you with the back-and-forth that goes with scheduling meetings over email. (For more robot helpers, check out this post.)

Inspiring Reads

Reading is a big part of the process for all three professionals, and here are some of their top suggestions:

  • A Whole New Mind: Why Right-Brainers will Rule the Future by Daniel H. Pink: Nita is obsessed with this book, which details the six human abilities that are essential for professional success and personal fulfillment in the future.
  • Value-Based Pricing by Harry Macdivitt: It’s a piece of advice that creatives get all the time: “Don’t price per hour. Price for value.” Of course, the inevitable question is, “How?” This book dives into the nitty gritty of creating a pricing strategy, and a step-by-step process for how to implement it. Hooray for actionable steps!
  • OkDork from Noah Kagan: Everyone loves a good business hack. The OkDork blog is filled with tips for growing your company, marketing like a pro, and upping your productivity. Plus, there’s lots of taco references.
  • Various works by Tim Ferriss, the original goldmine of life hacks for personal development. His site is a great starting point for useful information about everything from the slow-carb diet to mentorship and writing skills.

Daily Practices

Nita recommends having a regular practice that enhances self-awareness—the skill that will lead you to your professional desires. This could include:

  • Morning pages: This daily ritual is highly recommended in The Artist’s Way. The general practice is to empty your mind by writing for 10 minutes immediately after waking. Pro tip: End yours with a list of things you’re grateful for, as well as some affirmations for the day.
  • Meditation: No surprise here. Meditation improves productivity, increases feelings of wellbeing, and deepens sleep. All good things! For some really wonderful guided meditations, check out resources by Tara Brach.
  • Yoga: There’s a reason why so many offices are offering yoga these days. A good session will help you focus more deeply, become less anxious, and put a smile on your face. Plus, yoga boosts your immune system–– which means fewer sick days and more vacation!

Unlock Your Time

Working for less than half the week can seem like an impossible dream. Yet in reality, reaching that milestone requires the same type of effort that you would put into any other work endeavor: Become known for your skills, build closer business relationships, and learn how to take ownership over every aspect of your life.

Even exploring the concept will reveal a lot about yourself, says Keen: “I’ve been kind of forced to rise to the occasion, which has helped me learn a lot of things about myself.”

Adds Nita: “Working for myself changed my whole perspective on what it means to create in the world. Working for three days a week wasn’t just about changing my schedule. It became redefining what my life was about. I’m not a worker anymore. I’m a creator.”

If these stories are any indication of what’s possible, Freedom Friday might not be so far away after all.

Next: Find Work-Life Focus: A Trello Insider’s Guide To Personal Productivity


Learn the secrets of 3 people who mastered the 3 day workweek