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Five simple strategies to help you switch from a job you loathe to one you love

Want to find time for what matters? The 21 Day Timehacker Project matches readers with coaches who help them find time for their most important goals.

DAY ONE: What do you do when you love your hobby more than your job but you also have a wife, who works as a teacher, four young kids and bills to pay? That’s the situation Chris Boyle, 46, of Port Austin, Michigan, a lawyer by vocation and the proud owner of a kayak rental shop by avocation, had found himself in when he reached out to the Timehacker Project.

Boyle had just bought a foreclosed marina, and dreamed of opening a restaurant and beer garden for people going to and fro by boat to nearby Turnip Rock and other places. That combined with his kayaking business would be the ideal full-time job, he fantasized.

“I do litigation, which revolves around people who can’t seem to cooperate with the world,” said Boyle, he runs his own private practice. “I opened the kayak shop nine years ago on the side, just for fun, and I found I really enjoyed the customer service end of it. There’s nothing better than making people happy on vacation.” But he was too busy to see his way to his dream job.

THE TIME HACKS: Boyle worked with coach Jill Farmer, of St. Louis, Missouri. She suggested five time hacks:

1. Shift your perspective: Boyle thought that if he could just spend more time in the kayak shop, he could get it to grow faster, which would help him make the transition faster. So he often found himself feeling a little resentful when he was at his law office.Instead of looking at his law practice as a weight around his neck, I suggested Chris look at it as a way to build a bridge to the next phase of his life,” Farmer said.

2. Make over your To Do List: “Chris’s To Do list was more of a holding place for dormant ideas, than a list of action items,” Farmer said. She suggested he think about the upcoming week every Sunday. “I encouraged him to do a brain dump of all the ideas or tasks that he thinks needed to be done for both his law practice and the other business. Then, to plug in specific actions on specific days/times on his calendar, making sure that he leaves about half of his day unscheduled to allow for unexpected things that invariably pop up.”

Farmer encouraged him to have a daily To Do list with no more than 5 items. “I encouraged him to take some form of action, even a ridiculously easy step, on some of the important aspects of his business that hadn’t gotten attention lately,” she said.

“Finally, I encouraged him to use what I call a two-minute task list to collect the little tiny items that tend to distract us or pile up and set a timer to get those tackled at one specific time each day.”

[Related: How an entrepreneur stopped chasing every new idea so he could focus on one big goal]

3. Define your schedule:Chris recognized that he needed a clearer definition of his schedule,” Farmer said. She suggested that when Boyle planned his week that he block out 7 to 9 am for focusing on the most important priorities. “In the past, he’s had a loose idea of what “needed” or “should” get done, and then e-mails, calls and new things coming in the door would get him sidetracked,” she said.

“When Chris starts his day focusing on making progress on the significant things that have tended to get pushed aside, he’s less likely to feel panicked, resentful and perpetually frustrated by all of the moving parts in his busy life,” she continued. “He won’t have that ‘How come I didn’t get anything done today?’ feeling at the end of the day.”

4. Sync your technology: Boyle was not only juggling many different activities, he also had different scheduling systems that he used for them, some on his phone and some on his personal computer. Farmer suggested bringing in a tech expert to help him sync all his technology, so he’d have access to everything on every device, giving him the ability to more efficiently work, schedule and track email from anywhere.

5. Stop with the ‘Shoulds’:Torn between his law office and his growing kayak enterprise, Boyle was always second guessing how he divided his time between the two. “To borrow an oft-used term from twelve-step programs, Chris was ‘shoulding’ all over himself. It was draining his energy and creativity,” Farmer said. “During our conversation, Chris also recognized that the same innovation that has helped him be a successful entrepreneur with the kayak and marina business, can come into play in his law practice, too. We spent quite a bit of time brainstorming ways he could lower overhead at his law practice so he could spend less time there, and give more focus to his kayak company to make it more profitable.”

POTENTIAL STUMBLING BLOCKS: As they worked together, Boyle said he felt he needed outside confirmation, or permission to take the next step. “I reminded him that his own inner guidance is always going to be his best compass,” she said. “He knows that means being clearer in his communication with colleagues and staff at both businesses and creating some clearer boundaries around his time.”

Waiting for permission is something many people struggle with, Farmer said. “When clients of mine are trying to move from an existing business/location into something completely different, sometimes they forget they have choices,” she said. “For instance, Chris is the co-owner of his own law practice, but he forgot that he has a say in the schedule he sets and the cases he takes or doesn’t take.”

[Related: This young recruiter learned that his lack of focus at work masked a deeper problem: He’d outgrown his job]

DAY 21: When I caught up with Boyle, his kayak business was really taking off. He’d started with 12 kayaks nearly a decade ago, and now has more than 50, as well as stand-up paddle boards and bikes to rent. His wife has been selling outdoor clothing, and that business is “exploding.” And his dream of making the transition looks closer than ever.

Though he attributes the boom to the outdoor community finally discovering the area he lives in, the timehacks have helped him make the most of it, he said. “I’m feeling very good right now, and a lot of it has to do with being able to manage my schedule,” he said. “I feel like I’m getting things done more quickly and more efficiently than ever.”

He’d hired someone to help him sync all his technology, relieving himself of what had been an immense “time suck,” he said.

He began planning his week ahead, not on Sundays, but on Thursday evenings or Fridays, shifting the priorities on his To Do list. Then he worked with his secretary to block time off on his calendar to work on the big projects, whether for his law practice, or his kayak business.

He also found, as Farmer had told him, that oftentimes, if you don’t answer email right away, the fires tend to resolve themselves. “That was definitely true,” he said. “There were days I wouldn’t open my email until noon. I got so much more done.”

He also created a handbook of employee expectations to give workers at the kayak shop more freedom to solve problems on their own.

But one of the biggest changes, he said, was shifting his perspective, and realizing change was possible. “I realized I’m not alone. And that I was kind of stuck in certain ways, but that those ways could change,” he said. “Jill… helped me see that this was not only a worthy dream, but that others had done it before, and there are good ways to get there.”

JILL FARMER’S TOP TIMEHACK: Spend a little time each Sunday night listing priorities for the coming week — the significant things that support your values, goals and growth. Then, block out time on your calendar to take steps on each of those priorities every single morning.

What about you? What’s one timehack you could try this week? I’m going to work on blocking out the morning hours for a big writing project instead of starting with emails that often  blow me off course. Leave a comment below and let us know!

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