Use This Plan to Shrink Your To-Do List (and Actually Start Having Fun Again)


“I didn’t know I could do that…”

These were Stephanie’s incredulous words when she was given permission to read fiction for the first time in a decade. This mother of four and solo entrepreneur had spent the last ten years in a whirlwind of diaper changes, homework sessions and professional photography, which left her very little time for anything else she loved – including Harry Potter.

I give Stephanie credit for being so devoted to her family and for being so selfless. But her martyr-strategy didn’t work out.

As she stopped doing fun little things, like reading fantasies or playing volleyball, she grew resentful of her role as a wife and mother, and even of the job she was passionate about. She let go of a very successful business because she couldn’t stand it anymore. Ditto for the relationship with her loving husband.

This supermom and entrepreneur lost almost everything because she forgot one simple fact of life:

You gotta do what you love.

Stephanie thought there was no other choice but to cease her favorite things. But she never signed an agreement that said she had to be miserable…she just stopped making time for the little things she loved. In a world where billions of kids need to be shuttled to school and practices, and where our to-do lists are ever expanding as the universe, millions of people make the same mistake as Stephanie. And it’s seriously impacting their happiness in life and at work.

Could you be one of them?

Read on to find out how you can experience the joy of doing what you love on a daily basis.

Shrink you ever expanding to-do lists

Let’s be real: when you have a list of essential household and professional activities (that literally has mildew on it, as was Stephanie’s case), the things you would love to do seem otiose at best. I mean, what’s a barefoot walk compared to a water-tank replacement, or a massive project at work? But here’s the thing…

Doing what you love gives you a sense of self-confidence and creativity that actually helps you make headway in your to-do lists. The problem is that most people can’t rationalize spending time on themselves when there are so many imperatives that rely solely on them—professionals can especially relate. The solution?

Start making weekly action plans for your to-do’s

There’s something about a massive pile of tasks that paralyzes. That was the case for Stephanie. She’d been putting off certain activities for up to five years; and when she even thought about that dreaded list, she felt incompetent. So she pushed it away. And when she thought about going for a hike or doing something else she loved, she felt too guilty about that evil list to take care of herself. I helped her break this cycle.

All that I did was shift Stephanie’s priorities for a few weeks. Where normally she’d spend her daily free time going to the gym or doing yoga, I gave her permission to tackle her to-do list instead. And on the weekends where she usually found herself dragged into pointless community meetings or charity dinners, I gave her permission to reject every request for her presence and to make serious progress on her to-dos.

After only two weeks of this “bull by the horns” approach, Stephanie called me crying. She felt like she could finally breathe. And better still, she’d just come back from the meditation retreat she’d been dying to go to for years.

Your Plan:

Mark this month as your war against procrastinations. Take one hour this week to write down everything that’s been bugging you for the last few years. Sort those tasks into big (over two hours) and small. Then break them down into weekly chunks: eg, “Week 1, Week 2, etc.”

You’ll have to create time for these long avoided tasks every day of this month, which might mean sacrificing your gym visit or yoga class, or any other thing you can reasonably skip out on in favor of getting your life back under control. But this is only temporary.

Then every weekday, schedule time for as many small procrastinations as you can in your daily planner–and definitely at least one. Plan to tackle your big ones on the weekends. Yes, this might temporarily come at the expense of other things you enjoy. But once you start making headway on your to-dos, you’ll honestly feel like a new person. Which doesn’t usually happen on your typical weekend picnics.

Expand your ever-shrinking love-to-dos: plan for fun!

Once you’ve created some breathing room through waging war against your to-dos, it’s time to get reacquainted with the things you love. First step is to write out a list of things you already know you love, and to pen down the things you would love to try.

For Stephanie, this list included beach volleyball, lunch with friends, daily meditation, gardening, hiking, editing photos of her family, organizing her house—yes, to my shock, people can love organizing—and reading fiction again.

Once she had the list, I gave Stephanie permission to spend daily and weekly time doing it all. This involved some boundary setting and strategy.

Set boundaries to protect your time

“How am I supposed to read for pleasure when I’m doing homework for four hours straight?!” she asked me.

I told her to stop doing homework for four hours straight with her boys. (Duh)

Stephanie forgot that she was the boss and could shift the schedule as she saw fit. So I suggested she take a 15-30 minute break for every hour of homework: that way she could relax, sip tea, read. And she loved it. The boys still got their homework done, and she was much more relaxed and present to them because she was taking breaks for things she enjoyed.

“I have ten years of family photos that need editing!”, Stephanie said. “Help!”

Since her kids went to bed at 8:30, I asked her what she did from then till her bedtime at 10:00.

“I have a glass of red wine and fall asleep watching TV,” she said. “That’s the only thing I feel like doing to relax because my days are so hectic.”

But she didn’t remotely love TV. And she felt she was relying too much on alcohol. So I had her schedule editing for pleasure from 8:30 to 9:30, and then to fall asleep with more fiction from 9:30 to 10:00. She loved it. This simple scheduling tool helped her regain her sense of self, and her spark for life. Stephanie alternated between three or four creative activities in this time slot, depending on what she’s feeling. And no matter what she does, she feels that joyful/balanced sweetspot that she’d been missing out on for so long.

Saying no

In order to fit in things like gardening, beach volleyball, and hiking, Stephanie had to relearn the word “no.” For years she’d been limping in to HOA and PTA and every other A meeting you can think of. She was resentful of being asked, and bitter about spending her time doing things she hated; but she never had the courage to just say no. So I had her set an objective:

Say no to everything you don’t absolutely want to do for a week

It was uncomfortable to think about, because she’d always been the yes person people instinctively relied. But after her first “no”—an unequivocal rejection of a weekend of shopping with an old college “frenemy”, Stephanie felt the power of increased boundaries. And when “no” became her default answer for everything she was on the fence about, she finally found time to do the hiking and meditating and sports and friend time that she craved. Which made life worth living again.


By taking massive action against her monstrous to-do list, Stephanie lifted herself from the life paralysis that so many of us find ourselves in. This gave her the confidence to start scheduling more of what she loved. And when she got serious about saying no and protecting her time, Stephanie created the balanced and fun-filled life she’d been after for over a decade – which included the work she was passionate about. You can do the same.

If you want an expert to guide you in this step-by-step process, consider my coaching services. 

Written by Daniel Dowling
I went from being a highschool and college dropout to writing for the world's best publications in two short years. I owe ALL my success to habits like mindfulness and journaling. - So I built Millennial Success to share those incredible habits with you!