3577: How to Avoid Early Retirement Failure by Jillian Johnsrud on Smart Retirement Strategies
Optimal Finance DailyMay 30, 2026
3577
00:10:05

3577: How to Avoid Early Retirement Failure by Jillian Johnsrud on Smart Retirement Strategies

Discover all of the podcasts in our network, search for specific episodes, get the Optimal Living Daily workbook, and learn more at: OLDPodcast.com.

Episode 3577:

Jillian Johnsrud compares life to a garden box, explaining how an unchecked career can crowd out relationships, hobbies, health, and purpose long before financial independence arrives. She shares a practical approach to early retirement success through pruning back work, taking mini-retirements, and nurturing small “seedlings” of meaningful activities so life after work feels fulfilling instead of empty.

Read along with the original article(s) here: https://www.jillianjohnsrud.com/how-to-avoid-early-retirement-failure/

Quotes to ponder:

"It’s okay to love your work. But if it’s stealing time, energy, and focus from other areas of your life, you’re going to have to work hard to keep it in check."

"While life might be like a box of chocolates, I’d say it’s more like a garden box."

"Focus on what you want your FI lifestyle to be and slowly start giving that more of your time and energy."

Learn more about your ad choices. Visit megaphone.fm/adchoices

[00:00:00] Dell PCs with Intel inside are built for the moments that matter. For the moments you plan and the ones you don't. Built for the busy days that turn into all night study sessions. The moment you're working from a cafe and realize every outlet's taken. The times you're deep in your flow and the absolute last thing you need is an auto update throwing off your momentum. That's why Dell builds tech that adapts to the way you actually work. Built with long lasting batteries so you're not scrambling for the moment.

[00:00:30] The closest outlet. And built in intelligence that makes updates around your schedule not in the middle of it. They don't build tech for tech sake. They build it for you. Find technology built for the way you work at Dell.com slash Dell PCs. Built for you.

[00:00:51] This is Optimal Finance Daily. How to Avoid Early Retirement Failure by Jillian Johnsrud of Jillian Johnsrud.com

[00:01:01] While life might be like a box of chocolates, I'd say it's more like a garden box. We each have a specific and finite amount of time and space to grow what matters to us. There's often a work plan, a family one, friends, hobbies or interests. At any point in time, each plant shares this finite resource of time, energy and focus. This is an analogy I use a lot with clients who are aiming for financial independence,

[00:01:28] want to take a mini retirement, want to take a mini retirement, or retire early. The trouble with those goals is that the work plan can start to overwhelm the other plans. It can become invasive, crowding out the smaller plans. For most people, work is where we spend 40 to 50 hours a week.

[00:01:46] So it's naturally a big plan. On the financial independence path, letting that work plant go wild is rewarded. You'll probably earn more, get promoted, and be able to invest more money. Especially if your work is meaningful, enjoyable, or you're very competent at it. That work plant becomes a bit like mint. I love mint. It's one of my favorite herbs.

[00:02:10] But left unchecked, it'll take over my entire herb garden. It will push out or stifle all the other plants. Staring at dirt. The trouble comes when you're well on your way to Phi and you're ready to make a change. Maybe it's a year off or retiring altogether. You have this massive work plant, but there hasn't been much space for anything else. The few other plants in there, like friends and family, are rather small plants in comparison.

[00:02:40] Other plants, like hobbies or volunteering, haven't had any space for years. If you pluck that giant work plan out, you're going to have a few small plants and a bunch of empty dirt. But if you think, once that work plan is gone, I can start a bunch of new plants from seed. I'll take up running, declutter my garage, make new friends, find some hobbies, and an exciting volunteer gig.

[00:03:04] Except, if you've ever started plants from seed, you know it's just staring at a big patch of dirt for a long time. It takes a lot of time to start things from scratch. I've probably had a hundred conversations with people who retired, stared at that patch of dirt for a few months, and then went out to find a new job. After 10 or 15 years of hustling to become FI, they just went back to work. Why?

[00:03:30] They gave up all that income, significance, and usefulness to stare at an empty garden box. Even if they didn't like their job, at least it was paying them money. This path seems to be the norm, especially in American culture. But because the transition into early retirement is so difficult, and more often than not fails, it's not the path I recommend to my coaching clients. What we do instead.

[00:03:56] While there's a temptation to get to FI as quickly as possible, there's a more productive and successful approach. Number one. Prune it back. I love mint. It's one of my favorites in my herb garden, but it grows so easily and spreads so easily that it can become invasive. So in order to protect my other herbs, I aggressively prune back the mint. It's okay to love your work, but if it's stealing time, energy, and focus from other areas of your life,

[00:04:24] you're going to have to work hard to keep it in check. A lot of my clients are in the prune it back phase. They're asking to work from home to get back the commute time. They're leaving at three each day or going part-time. They're pruning back the work plan in order to give their other plants the space, sun, and soil to grow and thrive. There are other things in life they value, and they are ready to see those things expand and have a bigger role in their life. Number two.

[00:04:54] Mini retirements. Sometimes it's not possible to prune back a work plan, so it gets removed temporarily. I have clients taking a few months off to a year or two. They're pulling out that work plan and giving other areas of their life some space. Mini retirements are a great chance to add some new plants as well. Big health goals, declutter goals, travel, adventure, and rest. Mini retirements are like a test run.

[00:05:22] They allow you to practice your ideal FI lifestyle. It's less daunting to take a few months off than retire for 30 years. So while they might feel a little uncomfortable staring at a bit of dirt, they know it's just a short season to do their best to fill up their garden with new things. When people have let their work plan overwhelm everything, I give them about a 20% chance of staying retired. But the more mini retirements they've taken, the better those odds get.

[00:05:53] When I meet people who have taken four to five career breaks over the last 20 years, they're almost guaranteed to be successful and happy in retirement. They've had lots of practice, mastered the learning curve, and usually prioritize those other areas of life. And number three, seedlings. You might not be able to prune back your work or start a mini retirement today. Often clients come to me about six months before their mini retirement will start.

[00:06:21] In that case, I encourage people to start some seedlings. In the small moments, plant some seeds in little pots on your windowsill. Just like with the test and scale model, find a step you can take in one to four hours that will help to get a new plant started. Maybe it's researching pottery classes in your area. Maybe it's getting together with an old friend or trying a yoga class at the gym. Once you're able to prune back your work hours or take a mini retirement,

[00:06:50] you'll have some seedlings to go into the garden box. They won't be a full plant, but with this extra soil and sun and nutrients, they will fill in the empty space a lot faster than starting with seeds. Whatever you do, don't just keep your head down and push through at work, allowing it to overrun your life in order to get to five faster. Instead, focus on what you want your FI lifestyle to be and slowly start giving that more of your time and energy.

[00:07:18] That way, retiring early becomes a seamless transition instead of a jarring and dysregulating one. You just listened to the post titled How to Avoid Early Retirement Failure by Jillian Johnsrud of JillianJohnsrud.com Dell PCs with Intel inside are built for the moments that matter. For the moments you plan and the ones you don't.

[00:07:45] Built for the busy days that turn into all night study sessions. The moment you're working from a cafe and realize every outlet's taken. The times you're deep in your flow and the absolute last thing you need is an auto update throwing off your momentum. That's why Dell builds tech that adapts to the way you actually work. Built with long lasting batteries so you're not scrambling for the closest outlet. And built-in intelligence that makes updates around your schedule, not in the middle of it.

[00:08:15] They don't build tech for tech's sake. They build it for you. Find technology built for the way you work at dell.com slash dellpcs. Built for you. When you need to build up your team to handle the growing chaos at work, use Indeed Sponsored Jobs. It gives your job post the boost it needs to be seen and helps reach people with the right skills, certifications, and more.

[00:08:41] Spend less time searching and more time actually interviewing candidates who check all your boxes. Listeners of this show will get a $75 sponsored job credit at indeed.com slash podcast. That's indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed Sponsored Jobs. This article reminded me of some recent posts I saw in a FIRE subreddit. Early retirees shared that they were surprised at how hard it's been to fill the hole that not working has left in their lives.

[00:09:12] So I think Jillian offers some sound advice here. Don't wait to figure it out. If your goal is to retire early because you hate your job, it might be more beneficial to just find a job you like instead. Because ultimately, work and productivity in some capacity is important for our well-being. I like the advice from the pioneers who talk about creating a life that you don't need to retire from. And if that lifestyle includes working less or taking regular mini-retirements,

[00:09:41] you might even find the sweet spot where you're getting the best of both worlds. I've heard that the reward for early retirement, for many of us, is an existential crisis. When you're handed the keys to the castle and now have full autonomy over your time, and it can truly all be self-directed, this can actually be disorienting. So I like the advice in the article today. Start right now thinking about what you want to retire to, because it's likely more than just sleep.

[00:10:10] But that should do it for today. Thank you for listening. Have a great rest of your day. And I'll see you tomorrow, where your optimal life awaits.