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Should I travel when I'm In Debt?

Would love to hear about knocking out debt while you travel. Do you have any resources or advice?

How do you know if quitting your job is right for you?

How to know if quitting your job is right for you. Whether you should just do it and follow your gut, or think analytically about whether it's a good choice.

What's Your Opinion On "Job Hopping" and dealing with uncertainty?

Hey Jason, First, I just want to say I'm a huge fan of the podcast! I've been listening for about 9 months now and I love hearing about the different paths people can take to live a life of travel. As someone who didn't even know what a remote job was until recently, it's all really interesting to me, and I'm definitely learning ways to incorporate travel into my life as well. Keep up the great work! I wanted to get your opinion on "job hopping," and I know you've talked a little bit about this on your show. I'm only 23, and since graduating from college a little under 2 years ago, I've already held 3 different full-time jobs for different reasons- better paying, better related to my degree, etc. I recently applied to this seriously awesome job on Cool Works (thanks to listening to your show!). It's remote, would be within my skillset (sales & marketing), and I'd have much more freedom & flexibility to travel. The only problem is, it's seasonal from March-August. I spoke to the recruiter and asked if there would be any opportunity to extend this to a year-round position, and she said that it's definitely possible and they've asked people to stay before, but it definitely wouldn't be guaranteed. So basically, I'd have to leave my current job that I have been working at for 5 months, for this awesome opportunity, but then have to find something else at the end of it if I don't get the chance to stay on. I like but don't love my current job, it's definitely the best job I've held since being out of school, but the idea of being location independent is a dream I've had for a while now, and I don't know if I'd want to pass this up. On another hand, I don't want it to look bad to future employers that I've job hopped so much, but I know I'm still young, and isn't that what your twenties are for? Sorry for such a long message, but would love any insight or advice you could provide. Thanks again for all that you do. :)

Your Bonus Episode Suggestions Go Here!

Hey, 👋 it's Jason here! I created this thread as a place where you can leave your ideas and topic suggestions for the bonus episodes. I want to give you the bonus content YOU want and crowdsourcing is the best way to do that! So please, don't be shy and leave a comment with your thoughts and ideas!

Less joy in travel?

Do you find that your enjoyment of travel decreases over time? I am referring to the treadmill problem people have with purchases they make.