The Long Drive

My last post broke from the topic of work and business-building and, instead, grappled with the difficulty of facing up to failure and regret as it pertains to everyday life and the goals that we set for ourselves; more specifically, it dealt with the fact that my husband and I called it quits on our year abroad, because, apparently, international travel with two kids under 5 is a challenge I’m simply not up for at this juncture.

Now, back to our regularly-scheduled program…

Part V of the “Self-Annoyed: Solopreneurship Done Write” series, where I openly battle for control over my mindset + wrestle with cultural myths about success.

Suggested soundtrack: “Waiting For My Real Life to Begin” by Colin Hay.


I spent the first 18 years of my life watching my parents work hard. Really hard. As a result of this focused dedication to their labors, they were able to give me a good life, monetarily speaking. I wanted for nothing, attended posh private schools, spent holidays in far away places like Scotland, Europe and France, always had food on the table and the latest clothes in my closet (although, that didn’t stop me from dressing like an a**hole most of the time – teenagers!).

Sure, I can recall seasons when money was tighter than usual, but my parents worked hard to make sure that we always had enough. To this day, I admire my parents’ work ethic. They are both very intelligent, driven people. They’ve accomplished quite a lot in this brief life, and I’m proud to have inherited some of that drive – a relentless inner push to do more, keep going, get better. I wouldn’t have made it this far without it.

But, like most things in life, this drive is a double-sided coin: one side plunging me on toward bigger and better challenges, the other whispering that I’m not doing enough, not making enough of my life. It’s a real push-pull situation. A mental tug-of-war that, on my worst days, leaves me crumpled in a heap of sobs, feeling like a failure who’ll never measure up.

To complicate matters, I carry this deeply rooted ideal of giving more time to my kids than my parents were able to give – an ideal that, most of the time, seems in direct opposition to building a booming business. But then, it’s also sort of the point of this whole parenting thing, right? To be just a bit better, do just a bit more, or maybe just heal our own wounds by creating an alternate reality for our kids.

It’s hard to live out this vision, however, when, all the while, the voice inside of me shrieks: “BUT YOU HAVE TO BE SOMETHING!!!” And by that, of course, I mean “be famous” and “be rich.” 

To some degree, we all struggle with the feeling that success can only be accurately measured monetarily, that we don’t amount to much until we have a lot of things, or attention, or recognition.

It’s insidious. And try as we might to go against the grain, repeating to ourselves a mantra of “money doesn’t matter, people matter,” or “but I’m doing this for the passion of the work,” it’s always there at the periphery, threatening to get in.

A little over a year ago, I was happy to be making any amount of money writing, even just a couple hundred bucks. But the months slipped by, the familiar feeling of unworthiness came creeping back in, and suddenly I found myself applying for a corporate copywriting gig that I wasn’t even sure I wanted, primarily because I felt I needed someone on the outside to give me a title, a paycheck and some sense of self-worth. I ended up turning the job down, then lo and behold, along came a shiny new project or two and the next few months I made more money than I’d ever made before as a writer. I felt accomplished. I’d arrived. I was really something.

Then, I found out how much a fellow writer was making. It was about four times what I made during my most lucrative month in this profession, and just like that, I was nothing again.

On this road of entrepreneurship and business-building, it really doesn’t take much to go from “something” to “nothing.”

A conversation with a friend about income, a post on Facebook about how well an acquaintance is doing (or seems to be doing), facing up to the fact that you can’t afford to send your kids to private school, even though you, yourself, had a private school education… and oh my God, they’re going to resent me for being unable to provide them the lush lifestyle in which I grew up.

I have enough work, my husband and I can pay our bills, we can keep a roof over our heads. And still, sometimes, I find myself standing in front of the mirror, sizing up the woman I see before me who still feels so much like a little girl playing at a career. I spent yeeeaaarrrsss struggling to forge a real vocation by digging deep to figure out what it is that I’m meant to “do” with my life and who I want to “be,” striving to make my career something meaningful to me rather than just a means of earning a paycheck. Even after all of this time and the many hard lessons I’ve learned, I often feel I’m no closer to that goal than when I started. There are still so many confusing, complicated thoughts competing for dominance inside my muddled mind, for example:

I know that a career is something you build over time, taking on project after project, saying no to some things and yes to others, until you create a roughly-sewn patchwork blanket that somehow presents a cohesive picture…

… yet I still fight against the compulsion to neatly package my vocation into a presentable, recognizable package – a 3-minute elevator pitch that sums up who I am and what I’m about (as though it doesn’t change almost daily).

I know that my purpose and worth are so much more than what I do to earn money and that when I’m lying on my deathbed, the money I earned won’t mean half as much as the people I loved and those who loved me in return…

… but I do daily battle against the shame of being 32, not having all of my shit figured out and having to bunk with my parents for a few months to help reboot my savings after nine months of whimsical globetrotting.

This is the part where I’m supposed to offer a tidbit of advice for battling your inner demons and becoming a veritable ninja against the mental chaos that ravages the entrepreneurial soul. Sadly, I can offer you none. Truthfully, I don’t think anybody can. This is a battle you and I are going to have to face day in and day out, every step of our journey toward wherever it is we’re meant to be.

It’s little comfort, I know, but it’s something to just be in this battle. To sit and do your work, or whatever it is you love to do, eeking out your story while the chaos rages all around you, threatening to consume you from the inside out.

When it comes down to it, we all have to answer the question of what “success” really means, and the ability to choose how we pursue it counts for something, because there are many in our world who don’t get that choice.

Our answer may change moment to moment, depending on our whims, or something someone said about our work, or the fact that we ate too much for lunch, or didn’t get enough sleep last night. Most of the time, at least in my culture, money and fame seem like the only right answers, but there’s such important work being done in the world by people who don’t have either of those things and keep pushing and striving anyway, simply because the work is a sacred part of who they are.

Don’t get me wrong: I think it’s brave to work hard and earn a shit-ton of money. If I’m being honest, that’s what I want, too. If your passion aligns with a stellar income, you have hit the jackpot, my friend, and I salute you. I certainly wouldn’t say no to more money, and I know so many amazing, deserving people who work hard to build for themselves a lifestyle that mine may never match. But I’ve also come to understand that no amount of money will ever be “enough” for me, because there will always be more to get, more to buy, bigger houses, better cars. And all the money in the world will never keep me safe from the biggest, scariest things in life, like illness, death and loneliness.

So, let’s be brave, too, shall we?

Let’s do our work, whatever that looks like, even if it only matters to us and maybe three other people (who are our immediate family). Let’s do something that brings us to life, deepens our ability to love and be loved, connects us to a greater purpose and cultivates within us a humbling gratitude for the opportunity to do this work at all. We may never make a million dollars doing it and our kids may one day hate us for not being able to buy them the coolest shoes, hottest cars and trips to the Maldives… but what good is all of that stuff if we’re not truly “there” to enjoy it with them?

In a world filled with countless shiny things to run after, it seems to me that staying true to ourselves and present in each moment are the only things that really matter. You were given these gifts and that passion for a reason – why not use them to show us what success can look like? After all, it comes in as many different forms as there are people on this planet, and we could all use a reminder that money isn’t the only metric. In this season, friend, may you be richly blessed by the rewards of your work, monetary or otherwise, and may those blessings one day materialize in dollar signs (even though you don’t need them to feel validated), because making a good living doing what you love most would be the total tits.

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