Two Roads: Take the Harder One

If you’re at a crossroads and have to choose between two paths, take the more challenging one. And, I don’t mean the more challenging road by society’s standards, I mean the more challenging road for you personally, the road you might not even want to take because it looks difficult and narrow, and there’s no real certainty. There’s often more work involved too. I say take it anyway, because that’s the road that will lead to happiness.

Now that’s pretty countercultural, considering society really pushes that electric, adventurous, self-exploratory, do what makes you happy, if it’s too hard it’s not your strength, shape your destiny drug like a bonafide crack dealer, and man is it addictive. In fact, the crack dealer would likely call me a pessimist for suggesting anything other than the best, easiest, and most comfortable road for you. But here’s the truth as I see it, the easier road will get harder 100% of the time, and the harder road will get easier 100% of the time, so where would you rather be?

Because you’ll never be happier at the end of an easy road, but you’ll always be happier at the end of a harder one.

So if you’re at a crossroads and trying to decide what to do, here are a few suggestions based on my own experience…and missteps.

Choose The Road That Requires Commitment

I tend to be a bit of a free spirit, which served me well in young adulthood, but has really kicked my ass over the past couple of years. So when I finally met a really great guy who I actually cared about, I freaked out and ran. I’d been single so long that I’d forgotten how to be in a relationship and definitely felt overwhelmed. Commitment can feel blissfully suffocating if you’ve made freedom your prison. The easy road will always be the selfish road, but you’ll disguise it under: “If they were the right person it’d be easier” or “I’m just not ready.” Take it from me, they’re probably the right person and you’re probably ready.

Here’s something I’ve learned about commitment. It’ll feel more like a cozy blanket, hot cocoa, and cuddling by the fire than crazy electric fireworks. So when you’ve meet someone or something you feel crazy electric fireworks with, run. Run, fast. Because that’s the easy road, but when you’ve finally met something or someone you feel hot cocoa and warm blanket feelings with, keep them or it.

It took breaking up with someone I still care about to make me see how much my insatiable desire for freedom was undermining my happiness.

Commitment is hard. Relationships are definitely hard. But in the end, nobody’s perfect, and the hard roads always gets easier.

The Wrong Road Often Looks Like The Right One, Avoid It 

A little over a month ago, and on a whim, I applied for a job in San Francisco. It was a position at a big company that I never thought I’d actually hear back from, so when I did, I was pretty shocked. I was excited, but still felt a little uneasy about it because I’d already started a new job a few months back and never seriously considered leaving. Friends and family were excited for me though, and encouraged me to pursue it because it was insert cool company name here and I was starting to accumulate more bad memories than good in D.C.

It seemed like the right road, the right choice, and the best thing for me, so I continued on with the process making it past the first two rounds before my interview with one of the team leaders. Before the interview the thought crossed my mind that I was succumbing to my addiction again, but I ignored it, reasoning that this time was different because it was insert company here and it’d be a new city with new opportunities. But after my interview, I knew it was true, I was addicted to the thrill of newness.

Once I’d acknowledged this truth, I knew deep down that I wouldn’t get the job and I didn’t. Was I disappointed? Sure. But sometimes the easy road ends before you make a big mistake.

Knowing myself, my personality, and my own addictions, moving to San Francisco would have been the far easier road, and the road that would probably make me less happier in the end.

Do I feel like I’m settling by staying in D.C? I did at first. Do I feel like that now? Nope. Every day that I don’t apply for another job in San Francisco, Washington D.C. looks better, and I don’t think that’s a coincidence.

Peace is found in knowing the grass is never greener. It’s just another plot of grass. The moment you realize this, those “perfect easy roads” won’t look so perfect anymore.

Choose The Road With Less Choices

Research shows that the more choices we have, the less likely we are to choose anything. We think we want ten varieties of nail polish, but we really only want three. In fact, we’re more likely to choose something when the options are fewer, and we tend to be happier with those choices in the end.

I’ve found that creativity emerges with fewer choices. The fewer options you have, the more fun you have with the restrictions and the more you enjoy what you have. Remember college? No kitchen, no cookware, no problem. Whole meals were born from microwaves, hot water, and some kind of bowl. I can afford things now, but I can’t say I find the same enjoyment in eating as I did back then.

If you’re debating between two roads, choose the road that will force you to be more limited in some way, because ultimately those limitations (which look kinda shitty on the outside) will be to your enjoyment later.

Choose Little Inconveniences Daily 

I decided to walk home yesterday. It was a nice day, and while taking the metro was certainly faster and easier, I decided to walk from Foggy Bottom to Arlington instead. Part of me didn’t want to do it. I had things to do, walking would take longer, and I had a heavy bag, but I told myself that’s exactly why I needed to walk. I’d enjoy it more in the end. I walked along the Georgetown waterfront, popped into a store or two, walked across the Key Bridge, ordered a medium fry, a four piece nugget, and a strawberry Fanta at McDonalds (an easy choice that I probably could have skipped), and stumbled upon an outdoor concert in Rosslyn. I decided to sit down with said fast food and listen to the music for a bit. This was one of the songs:

Somewhere between:

The wild dogs cry out in the night
As they grow restless, longing for some solitary company
I know that I must do what’s right


It’s gonna take a lot to drag me away from you
There’s nothing that a hundred men or more could ever do
I bless the rains down in Africa
Gonna take some time to do the things we never had

I realized something.

I’ve been down some interesting roads over the past couple of years, but as I sat there tapping my food, surrounded by strangers on separate roads, making their own individual choices, I realized I was pretty damn happy.


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