Jet Setter Setback

When I got back from Folsom (yes, I’m mentioning Folsom one last time) at the end of September, I might have had a tiny, little nervous breakdown.  It had nothing to do with Folsom though.  Rather it was because my partner, Luke, and I were supposed to leave for yet another trip - this time to Portland.  And I only had five days between the two.  

Luke didn’t join me for the filthy San Fran street fair.  He is a bit of an introvert who doesn’t like big crowds, or dancing, or debauchery.  I, on the other hand, tend to thrive in these environments.  Though this shouldn't be surprising seeing as when we did our trip to Chicago back in July, I kind of ran us all over the bar scene.


Luke needed a vacation for him - something a little slower paced.  He had always loved the beauty and the easy vibe of Portland.  I had never been before but continuously heard about the great hiking, great beaches, great restaurants, and the male strippers who can go all the way nude.  This certainly sounded like a paradise to me.    

Plus, I could meet one of my favorite fellow bloggers, Michael James Schneider (  He’s a great writer and has the MOST clever photos on Instagram (see: @blcksmth).  And then I could do a photo shoot with Kenton Waltz (see: @kentonwaltz).  I’ve been enjoying his work on Instagram too.  And then I could go reconnect with one of my new found Folsom friends, Kevin (see: @pdx_saipp).  See how good I do at “relaxing?”

Between these trips, some folks have inquired how I’ve been able to live this jet setting lifestyle when I keep proclaiming to be a broke ass writer.  It all began earlier this year when Southwest Airlines lured me into signing up for their credit card with a 50,000 bonus point offer.  After researching their point system, I figured this could be good for two or three trips (depending on whether Luke traveled with me or not).

Then I discovered Southwest’s “Companion Pass” benefit.  All you have to do is reach 110,000 points in a calendar year, and then you could designate someone to fly with you for free for the remainder of that year and the year after that.  You could use this whether you booked flights with money or with points AND there was no limit on to how often you can use it.

However getting 110,000 points means spending $110,000 on the credit card.  Even if my 50,000 bonus points counted towards it, I’d still never spend sixty grand in a year.  That’s not what broke ass writers do.

This kind of irked me about Southwest’s Companion Pass.  It felt like it was just giving wealthy people more free shit.  I had a major Bernie Sander’s moment about it and began googling to see if I could find a way to cheat the system.  It didn’t take long before I discovered a solution.

According to several bloggers, these bonus points for new cards do count towards the Companion Pass.  So all you need to do, after getting your personal card, is to sign up for a business card and get an additional 60,000 bonus points.  All of these points funnel into the same account so it will equal 110,000 points.

There’s no way that Southwest will let people get away with that!  Right?  As I skimmed through these blog posts, I read a bunch of comments from readers who said they tried it and that it actually worked.  I already had the personal card for a couple of months.  Why not give it a shot?  

I haven’t ever applied for a business card before, so I was nervous.  Luckily I found another blog post that laid it all out for this exact situation (  I applied online describing myself as a sole proprietor.  The online response said they needed more time to process.  Like the business card blog suggested, I immediately called the reconsideration line.  The operator grilled me with the questions I had prepared for.  Then I waited anxiously while he put me on hold to determine my future travel fate.

After a few too many minutes, he returned and told me congratulations.  I had been approved!  I had been approved?!  But he didn’t ask for any proof of the information I gave him.  I could've made the whole thing up!  Instead I only made some of it up.  That makes me a decent person still… I think.

Once I spent the minimum amount to get that new 60,000 point bonus, I received yet another congratulations - this time from the airline saying I had, in fact, achieved the Companion Pass.  I could NOT believe this worked.  I immediately jumped online and began researching all of our options.  I became a man with a mission.  

Let’s book San Francisco to visit our friends in July!  Let’s book New Orleans in August for Southern Decadence!  I might as well go see one of my favorite bands in Seattle in September!  Oh wait, our San Franciscan friends can’t do July.  Well, let’s do Chicago for a do-over trip then!  Our first time there sucked.  

And I could just do San Francisco after Seattle for Folsom!  But wait, Luke wishes he could go to Seattle too!  He can’t because of work.  So I’ll just go back with him at the beginning of October!  No biggie!  We might as well start with Portland while we’re at it!   I’ve always wanted to go there.  Oh, and I’ve been dying to get back to San Diego!  I’ll just hop over there at the end of October!

Southwest makes it almost a little too easy to cancel your trips when you book with points.  So when Luke realized he’d hate Southern Decadence (remember: he’s an introvert), we nixed it and got our points back - no questions asked.  Same for when we canceled the initial trip to San Fran and then switched it to Chicago.  I’m not sure if this is how real jet setters act, but all of these bookings and unpunishable changes-of-mind were flooding my veins with oxytocin.  I couldn’t get enough.


What I didn’t account for was that, when you go on vacation, you don’t do any work - no matter how much you promise yourself that you will.  Maybe some adults do, but evidently I didn’t have the discipline for it.  In fact, I struggled with discipline even when I worked at home.  How did I think I could pull this off?

Amongst these travels, I’d try to work ahead.  Yet all it did was keep me at the bare minimum with The Bare InkSlinger.  I couldn’t get to the REALLY important stuff and the longer it started to take me, the more I felt like I was churning my wheels in a mud pit.  And this is how I became a total mess in the five days between my San Fran trip and our Portland/Seattle trip - so much to do, such little time… and I don’t work well under pressure.

I’d try to rip through my work during the day and break for the gym in the afternoon.  The gym provides a little escape where I can just go be brainless and lift heavy things for a while like a neanderthal.  Except when I’d get back home, I’d realize that I didn’t make enough headway and that my savings were starting to run out. My neanderthal high would quickly get replaced with depression.  

Luke would give me a welcome-home-hug to which I’d barely say a word.  Instead, I'd push him away so that I could go do more work in the office.  I would sit at the computer struggling to keep the stress at bay.  All this travel might be making my dreams slip from my fingertips and I didn’t know what to do.

Three days before the Portland trip, Luke stopped me on my way to the office.  “Love, I feel like you are mad at me,” he said.  With him being a therapist and my having been in social work, we have a knack for communicating what’s on our minds.  Oh, and “love” is our creepy (romantic) nickname for each other.

Knowing he felt this way broke my heart.  So like any well rounded human being, I went into full panic mode on him right then and there.  I grabbed him, and hugged him, and suddenly had trouble breathing.  I began shouting out random phrases of hopelessness into his chest.  I CAN’T GET ANYTHING DONE!  NONE OF THIS IS EVER GOING TO WORK!  I’M GOING TO HAVE TO GO DRIVE FOR UBER TO MAKE MONEY AND I’LL NEVER GET TO WRITE AGAIN!  I JUST NEED TO GIVE UP!

“Love, we have to cancel the Portland trip.”

“What?  Oh, no.  That’s not an option,” I told him as I headed back to the office to go do more work (smart, huh?).

I couldn’t dare cancel.  Michael (the blogger) and I were supposed to collaborate on one of his awesome photos and maybe even a blog post.  I had a photoshoot lined up with Kenton (the photographer).  We were supposed to get drinks with Kevin (the Folsom friend).  And Patrick (the Portland host) had already blocked off time to let us stay with him.

Still, none of this convinced Luke that the trip was a good idea and he continued to try to talk some sense into me (that bastard).  However, it wasn’t just about these other people I hated canceling on.  I didn’t want to cancel because this would be the only chance Luke could travel with me for a while.  He didn’t get to join me in Seattle or San Francisco and I’d be going to San Diego without him too.  It wasn't fair.

Luke admitted that he would be sad to not go on the trip.  But then again, he would be more sad if I didn’t succeed at my dream of writing.  He believed in my work and, for him, making it happen was the most important thing in the world.  

I felt awful.  I felt selfish.  I got to go on these other trips and he would have to forgo his.  But telling yourself things like this does not help cure nervous breakdowns - not even a small one.  It only increased my anxiety more.  Luke asked me to give it some serious and realistic thought.

The next evening, I got a phone call that my father went into the hospital with chest pains.  They would run some tests and keep him over night for observations.  Everything turned out fine, but this clearly felt like the universe was telling me a message: slow down - pay attention to the things that need paying attention to (sometimes the universe doesn’t have the best grammar).

I took a step back along with a deep breath.  My mistake had become painstakingly clear.  I was too much of a sucker for a good deal and I thought if we didn’t take advantage of all this free travel, then we’d be missing out on the opportunity of a lifetime.  But this lifetime opportunity was impacting my life right now.  Becoming a jet setter had become more of a setback.

To be honest, the travel was hardly even fun anymore.  It became like a drug.  Getting on that airplane gave me an immediate high.  But returning back home felt like I needed to go to some travel based methadone clinic.  This had to stop.

I cancelled the Portland trip and we got our points back.  When I texted the Portland peeps, they were disappointed, but kind and empathetic. And although my heart weighed heavy that Luke and I weren’t enjoying a vacation together, a weight was simultaneously lifting off of my shoulders - making it easier to breathe again over the coming days.  Oh, and I decided to increase my mental health medications too.  

Luke’s sacrifice also did something else for me.  It kicked me in the ass to focus harder and have more discipline in my work.  If he had to give up his vacation, then I had to make my time worth his while.  I couldn’t let it all be for nothing.  So during the days we should’ve been in Portland, I put my head down and wrote like a crackhead who’s jonesing for his next flight.  I finally got the headway I needed in my work.  

I’m slowly starting to understand an unfortunate reality: the more I try to do everything, the less likely I will ever accomplish anything.  And I will never be able to slow down when I continue to fill my life with a hundred different adventures.  I don’t want to end up in the hospital with my own set of chest pains.  Luke and I might have the travel opportunity of a lifetime, but, in the end, I won’t get anywhere as long as I keep trying to go everywhere.


Edited by Glen Trupp

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