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Living an Unscheduled Life

Bushwhack Canister

Guthook said, “I want to see how long I can lead a life without a fixed schedule” when we were hiking in the mountains the other day. We’d blown off work for the day, an easy thing to do since we both mainly work for ourselves, but have a few part-time jobs on the side too.

I keep meeting more and more people like us who opt to take part-time or even seasonal jobs over full-time ones out of choice because they like having a lot of unstructured time to do what they want.  It’s probably not a coincidence that they’re all involved with outdoor recreation in some way. I’m not suggesting that you drop your full-time job and switch to a frugal lifestyle – I’m just observing that more and more people I know are opting for less money and less certain employment in exchange for more TIME.

Speaking for myself, I jumped off the corporate treadmill a bit over 10 years ago, and I can’t believe how much happier and productive I’ve become by working for myself and having lots of free time. Time to see my friends, time to volunteer in my community, time go on lots of hikes, eat dinner with my wife every night, take an afternoon nap, borrow books from the library, take classes at the gym – none of which I fit into my schedule when I worked full time for someone else.

Contrary to what you might think, pulling together lots of intermittent income sources is far less stressful than hanging onto one for dear life. There are no office politics to play, no deranged bosses to appease, and the commute is way easier. In fact, I argue that being able to generate secondary sources of income is a vital survival skill in our economy since there’s no such thing as a sure job anymore. If you want a safety net, make your own.

But the point of this post is not about making money as much as it is about having more free and unscheduled time to savor your life. If you want to make something, make yourself more time.


  1. Give me Time and a Refuge. I think you’ve really hit on something with this blog entry. A voice from the wilderness. Thanks for the peek inside the looking glass of the outdoors blogosphere. There must be a few others who feel they are getting robbed of their ever-diminishing time while being conflicted with the demands to work longer, harder and pay up ever-higher bills and (the 800lb gorilla in the room) amid a world that is daily mounting up evidence of imminent crisis and conflict.

    • Ryan said it, but it’s a theme that has been building inside me and I wanted to write about. Maybe the afterword should be titled “Living an Uninterrupted Life”. Once you give yourself a bit more time, you rally can SAVOR your moments and not be switching back and forth between different half-finished projects all of the time. That’s ultimately what drove me away from full time employment to something slower and more deeply fulfilling.

  2. Happy to work at a job with plenty of vacation & personal time, but still longing for more time in the woods!

  3. You got it right! I am somewhere in between. Exchanged stressful full time job for lower paying but more flexible lower paying full time job that allows me 3 day weekends. Having much more fun now!

    • I can’t tell you how many people I know who also have 4 day/full time jobs too. It’s completely doable if you shift your priorities a bit but it’s a hard hurdle to get over for a lot of people. I understand that.

  4. I’ve done both, my current job (3-12 hour days) works out best for me. While self employed the job was always there, now when I punch out it is over and it is off of my mind. Another key point is that neither of you have children.

    • I think there’s a certain confidence you have to feel about your ability to get a full time job if you need one. I have no doubts that I could get hired quickly if I wanted to go back to a full time job working for someone else, but I find it a lot more fun to sell projects to clients that I like and work with them to help them succeed.

    • There’s a lot of issues here. I don’t know how old most of you are, but at a certain point you will not get hired, despite age discrimination laws.
      Healthcare and benefits. When i was younger i never got sick, had a healthy life style and still do. BUT, the machine wears out. What do you do about healthcare and medical bills on a part time wage?
      Retirement. Old age comes fast. Faster than you think. How do you save for that on a part time wage?
      Kids. It all goes out the window when they enter the picture.
      I love the idea of more time living an authentic life, If nothing else, the lockdown with this pandemic has brought that to the forefront, but…

      • I’ve had health insurance since I quit my corporate job. We may be working part-time, but that doesn’t mean we don’t earn a living wage. Yeah, the Pandemic. But all the more reason to cut loose of the Borg. If you control your destiny and make it Pandemic-proof (think plumbing), you’ll never have some ass-whipe manager lay you off.

  5. …and I also have an extremely fulfilling job ICU nurse) which helps and I work with a group of great people.

  6. I love the thought here, and very much agree with it. For some people. In general our society has too little focus on the wilderness as evidenced by our popular culture, politics, and laws. And the dismissal of information that show the importance of the wilderness in creating and maintaining a healthy lifestyle is on the verge of depressing. HOWEVER, as someone who loves the woods, yet makes very little income this seems to me to be, at best a “grass is greener” thought for corporate/formerly-corporate types. Although there has been 2 years (plenty of time) to evaluate your decision and decide that it is right for you, you have done so after years of being able to accrue assets and savings. As someone who lives a frugal lifestyle, the stress of being very close to the poverty line isn’t as simple as trading in a higher paying, scheduled job for one with less income/more flexibility/greater chance to go outside. I make financial sacrifices to get deep into the woods when doing so is a prudent, rational decision. Unfortunately jobs that offer you a limited work week but are still financially viable for someone to live with (and hopefully one day start a family) aren’t always available. making it even more difficult is that many younger people like myself either don’t have a large arsenal of skills, experience or connections to allow them to create their own business or find a more flexible job.

    Without being too contrarian, the notion that “Contrary to what you might think, pulling together lots of intermittent income sources is far less stressful than hanging onto one for dear life” is, at best, a very subjective, and it is dependent on the income sources. I have several income sources and I am still required to appease a deranged boss, play politics, and commute (although my commute is actually quite reasonable and often enjoyable!).

    I realize this mini-diatribe falls into the trap you cautioned against-that this post is about TIME, not money, but I think the subject and comments show that they are not inextricable from one another. Unfortunately.

    • Yep – I don’t disagree. Having some assets, savings, and a life time of skills helps immensely, but I also know many younger people, like Ryan, who made a choice early on not to spend all of their time on making money and have succeeded in developing the skills to acquire paying work without ruining their lives over it. They still travel, bake, hike, read, write, have relationships, etc.

      Speaking for myself, the key was in figuring out how to work remotely outside an office. The internet has opened up huge opportunities for self-employment or remote employment that never existed before. If you know how to propose and package your skills, it is easy to charge less than other established businesses and provide just as much value, if not more. Nothing comes for free of course, and you have to get those skills and develop the chutzpah to go out and sell them. But younger people do this too and not just us old farts.

  7. I retired in 2006 after 27 years of self employment in the high stress world of advertising, then recently accepted a part time job with one of the best companies in the world. No stress,, no worries, great coworkers and we’re encouraged to take time off to enjoy the outdoors.

  8. Well said & is precisely my story as well and my wife & I have 2 very active kids. THIS CAN BE DONE!! What I’ve also experienced is that, with smart & sat-phones, having my own firm, + now being able to FAR more efficiently concentrate my efforts on what really matters = I’m reasonably adept at in the business world, I’m actually producing more income than when I was the big corporate guy with 175 emails/day, 5 conference calls on Mondays & Fridays, non-stop travel & a grumpy boss. Now, I’m the boss & my Golden Retreiver is my able assistant. And so, he & I are headed to the AT here in GA tomorrow 1st light, or maybe we’ll take the canoe out & go for a long paddle!!

    • First off – congratulations. You have obviously got a handle on this and are living a good life.

      When you cut out all of the inter-personal communication imposed by a multi-person business and focus only on value generation you can save an enormous amount of personal time for yourself. Conference calls….man I haven’t been on one of those for years now. Don’t miss them one bit.

  9. “…time to go on lots of hikes…” — definitely one of the nicest perks you get when you work for yourself. Glad for you. I’m getting ready to leave the corporate treadmill as well.

  10. Excellent post. I retired early and am blessed to have a pension after working the exact same job for 25 years. I make more money than when I was working for the man. There is one other mantra that we need to hear on this thread: ” People who live in small houses can afford to relax” . It’s all about overhead, staying away from new cars. $50,000 kitchen renovations, etc.

  11. I love this thread. Thanks for all that have shared. I spend half my time worrying about my job, as it is substantial monetarily, and stressful no doubt. Travel etc…2 young kids. We love the woods. It is tough to not ride this train, and tough not to step off…..


  12. Double negative, sorry… Hopefully you get my point.

  13. I work as an adjunct professor, and have been constantly lamenting having to juggle classes at two different schools and constantly thinking I need to add .a third and have been wishing for a full time job instead. But. I have the freedom to take August and travel, I don’t have to be at school. If I can juggle the money, I could also conceivably take a semester and a summer off and go through hike something, and my job would be there (or one like it), when I get back. Thanks for writing this, it’s reminded me to look at the benefits of my situation.

  14. Everyday I wish for that kind of life but sadly just don’t know how to achieve that. If you have advanced degrees and or consulting/freelance experience then maybe it’s easier but the challenge for myself and many other middle class citizens is how to getvthis kind of freedom.. The reality is most of us are stuck and don’t even know where to begin to get off the crazy train and have a way of making a living while still being able to enjoy life…

  15. Ok, how do people pull together health insurance from a series of part-time or short-duration jobs? This seems like one of the biggest stumbling blocks to me right now, and i have a job where I get 3.5 months off every year…

  16. I planned my corporate exit for a year and left it with a smile on my face late 2014. I sold my house, second car and all my furniture, reducing my belongings to one car, 13 boxes sitting in a storage unit, one carry on suitcase and a large tote. (reducing my bills to include my cellphone and car related responsibilities such as registration, upkeep etc.) I have traveled quite a bit from SE Asia, to Kenya and throughout Europe and loved every minute of it! Last summer I spent 3 months in Shelburn New Hampshire where I found my love for hiking, peaking 47 mountains, including all the mountains on AMC’s Map 6 plus others including Mt. Washington. I was able to hike 20+ this year from map 5, but had to leave early due to my first grandchild being born in California! I am currently hiking in Ireland and have been planning for over a year now to hike the PCT which will find me at the southern terminus in April. Yes, I have the time to hike the PCT! This isn’t the lifestyle for everyone, but I love it!

  17. How do you deal with health insurance? Go without?

  18. As a retired teacher, I have/had a part of that. Worked 180 days a year, 3 weeks off at Xmas, another week at Spring (Not Easter), lots of time that can be moved off the plate if spare time is needed (the papers still need to be graded, but I can set the schedule), worked with good people and made decent money. Good retirement and lifetime health insurance, a PPO no less and free. There is plenty of downside but you need to keep your eye on the ball–The upside is more than worth the downside.
    I started in my mid-fifties and had to pick up some units before I could get into a two year credential program. All schools need English teachers since it is the only subject that is taught every semester of every year. Get some advice before you take the leap, because there is much more to it than I’ve covered here, but I have been happily retired for ten years now and still get my mountain time.

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