The Path to Self-Employment

I left a secure job in Los Angeles to follow my goals of being my own boss and to write full time. It has only been two months but I am learning that our honest gifts must be cultivated with care, despite any distractions.

Cabo San Lucas, Mexico. No, my days are not all traced in cloud-light with sunfish licking at the yachts hull, but this smile has stayed with me. Because chasing what you love brings a sustained bliss that far outlasts a temporary vaca.

Cabo San Lucas, Mexico. No, my days are not all traced in cloud-light with sunfish licking at the yachts hull, but this smile has stayed with me. Because chasing what you love brings a sustained bliss that far outlasts a temporary vaca.


I have spoken with many people over the last few years, of all ages, who continue to look for meaning in a corporate institution where it just may not exist. The search for bliss, or at the very least a sense of fulfillment at the end of each work day is something we all want, and in my opinion, something we need. I probably won’t be the the first to tell you and I most definitely won’t be the last, but this visceral and palpable thing you are searching for may very well be outside the comforts of the corporate container. I may still be looking for it but this severing of the umbilical was my first step in getting there. And if this post has any impact on you, my patient reader, it is to remind you that your path does not look like anyone else’s. At a glance, sure. But when you begin to remove everybody else (and their judgment) from your narrative, it becomes a helluva lot easier to create from an identity and a passion that is uniquely yours.

Create from an identity and a passion that is uniquely yours

My biggest challenge since taking a job as a digital marketing associate for a luxury lifestyle magazine was securing an identity that felt true to me. It was so important, in fact, that I spent two years trying to prove that I had a voice and that I wanted to be a part of the editorial conversation, not just the monotonous daily grind that had little room for creativity. After our boutique brand was acquired by one of the largest publishing companies in the world, I was given the opportunity—by the CEO nonetheless—to start contributing content to the website. This was my break. As part of my previous workflow was parceled off to editors and interns, I had time to write, to research, to review press releases, source imagery, and work with editors on how to angle and approach this specific type of luxury content. I was excited to be included in the content creation process as it was a stimulating workflow that included reviewing experiences and products from around the world: Riad’s in Marrakech, million-dollar bottles of auctioned whiskies, innovative wellness centers, rooftop penthouses in NYC, opulent safari excursions in South Africa, and so much more. I took this opportunity and ran with it. Because if I have learned anything, it is that these small chances to be seen are necessary to take, even if the vision of where you are headed is not guaranteed.

Emotions, even those that seem painful in the short term, are truly like an internal compass that point you towards the actions you must take to arrive at your goals.
— Anthony Robbins 

I would continue to do this corporate dance for about a year. Contributing my words as often as I could and keeping my job secured after two major layoffs would reduce our team to half its size. Our office would make the move from the seaside city of Malibu to the concrete jungle of West L.A. and prove that publishing is even more cut-throat than we thought. Especially when you have a monthly print magazine produced under a company that has no previous experience with this unique business. Despite the rocky on-boarding to the new digs, I learned as much as I could about digital publishing, marketing, ethical journalism, social media, copy-editing, and the professional ins and outs of getting your way in a rule-laden corporate setting. I figured out how to appropriately ask for a raise, how to inappropriately voice your frustrations (and then apologize), when to stand up for yourself, and when to humbly sit down and let the system work out its inefficiencies on their own. When things flatlined with the writing and I became bored of recreating press releases for a money hungry audience, I started to look into other departments for opportunities. It was a risk to offer my help and voice to other sectors of the brand, but there was something loud within me that pushed me to look at every possibility here at the company. I even looked at other publications that we shared a parent company with (Variety, Footwear News, Women’s Wear Daily) to seek publication opportunities and to bridge our brands audiences and grow our online identities by getting bylines on other sites and practicing a different editorial tone of voice. This did not all go smoothly, in fact, I hit so many walls that I began to realize that my career in this steel-wrapped mini skyscraper may not be where I belong anymore. I quietly retreated behind my work, walking the halls with a convincing confidence, engaging in projects with an attempted enthusiasm, all while plotting my way out.

“I am losing precious days. I am degenerating into a machine for making money. I am learning nothing in this trivial world of men. I must break away and get out into the mountains to learn the news.”
— John Muir

My anxiety some days was so bad that I began working from home once a week to keep my sanity somewhat intact. The white-washed walls and low vibrations that hummed through the AC chilled hallways was followed by lackluster looks from executives upstairs. It all left me feeling alone and unsupportive of someone else’s agenda. I am not a typically depressive person. I look for inspiration and silver-linings in most scenarios (and in most people), but after my two-year anniversary at the magazine hit, I felt a darkness float over me that I couldn’t shake. It was a feeling of dishonesty. I had put my own passion projects aside to prove my worth at work, as if that was the most important thing. My ego got in the way of my truth. A cloudy forecast determined months of not doing what I love, instead promoting somebody else’s stories rather than telling my own. I was a message maker pushing products that were far from my reality. I waded in waters that reflected my own obedience to ideas and lifestyles that did'n’t blend well with me. Like oil and water. I was separated from the work, the luxury speak, and couldn’t stand behind the granule debates over which brands rule over the others, and the stresses that I saw each co-worker hoist onto their backs at 6:00 pm and take with them out the door. These events all led me to course correct. To glance inwards at my inner compass and take a self-scan in order to make a change. The thing is, I knew who I was all along. I have always been my truest when I am writing creatively, pouring out raw self-expression with the intent to invoke feeling in my readers. That is exactly what exhilarates me in the now.

This simple acknowledgment led me to start doing outreach for other job opportunities in LA and beyond, looking into editorial roles and marketing-focused jobs (Netflix, Tesla, Vice) that would expand on my existing knowledge but allow me to grow upwards versus laterally. I even thought about quitting and living off my savings, moving into a busted studio in Venice, and even booking a one-way ticket to Colombia. Looking back, I am somewhat thankful that none of those job opportunities worked out and I am proud for not running at the first exit sign. For this would all lead me forward to a place of personal growth that is achieved by being self-driven and personally accountable for every step towards success—and failure.

This transition into owning my honesty truly began when I let go of everything that once defined my life in Malibu and in the city. I let go of the box seats at the Staples Center, happy hour on chic rooftops downtown, the privilege and access I had to incredible multi-cultural food, open mic nights at legendary poetry lounges, weekend trips to the desert and to Santa Barbara, and finally, letting go of my beachy bungalow that had been my spiritual crash pad for four years. This and all the other moments I had occupied were simply borrowed spaces. I had done my work, I had tapped the city—although some Angeleno natives would say I only scratched the surface—and I was releasing control of what I foolishly thought was mine to keep all along. It all unraveled from there. The tangle of mistrust was unknotting and with it came a refreshing acceptance that my journey needed to continue beyond the confines of everything I thought was possible.

My ability to accept support and help when I needed it, was me declaring trust in myself

I put in my three-week notice with restrained enthusiasm and began announcing my departure to friends and family. With the most confidence I had debuted all year, I would tell everyone I was moving back to Boulder, CO. A place I never imagined coming back to for an extended stay. My ability to accept support and help when I needed it was me declaring trust in myself. A trust strong enough to keep my lofty goals of traveling Latin America and committing to a career in writing and journalism to remain at the forefront, even if it means moving home. A temporary layover I am calling it :)

Before my final departure, I remained in the constant hustle of daily digital publishing. The clocks ticked on around me, deadlines loomed, and the stale air tightened in my lungs. Co-workers and editors fell in sync with the daily grind and I played my part off to the side, waiting for the bell to ring. On my very last day, I departed with genuine gratitude for the experiences and editorial voice I had gained, but I was leaving with an assurance that this move was going to be the best thing to happen to my career.

I left the nine-story building with salty eyes, saying goodbye to a few favorite faces, and then choking in the exhaust-filled air hanging low over Santa Monica Blvd. Between breaths, I smiled big, knowing all too well that this was the beginning of something undefined in a culture of fixed identities. Leaving this steady job with benefits, familiarity, and some industry perks was a decision that took nearly a year to follow through with but it was not until I made the clear decision to leave that I was truly ready to leap beyond the cubicle and journey back to my truth. To reclaim the appetite inside that kept me up at night. You know, that desire so strong it doesn’t let you settle until its addressed? Well, this desire took me months to understand and to eventually believe in but it manifested into a decision. And as my father tells me, life is simply a series of decisions.

Departing a city I fell in love with and people that I would call family was a deep confirmation that I had sipped in this wild landscape with abundant mouthfuls and untenured inquisition. I was leaving on a full stomach.

Impromptu photoshoot atop the PMC helipad. A final wave goodbye to my life in Los Angeles.

Impromptu photoshoot atop the PMC helipad. A final wave goodbye to my life in Los Angeles.

One sure way to know you are headed in the right direction is when you receive creative signs from the universe thus aligning your trust and confirming your step work. My last day in the office was on my cousin Will’s birthday. I cried the moment I saw the dates line up, for his life has taught me to not waste my time being anything other than me, and his creative spirit is always channeled in the work that I put out. The other significant dates fell on my grandfather Joe’s birthday, my cousin Mallory’s birthday (whom we also lost too soon), and on lucky numbers that always seem to appear in those moments I need affirmation.

I packed up a home, threw a few parties, purged most of my belongings, scarfed a Lily’s burrito by the beach, and blasted Tame Impala all the way through the dense metropolis of Los Angeles on September first. I headed east for Colorado on a three-week road trip that would take me across Arizona, New Mexico, and southwest Colorado. I made pitstops in Sedona, Santa Fe, Española, Durango, and Silverton. I re-connected with old friends and family, stomped on ground that once held my adolescence, smoked spliffs on the hood of the car in the middle of dusty nowhere, stood on the rim of the world’s first proven crater, did yoga at the base of Cathedral Mountain at the site of a spiritual vortex, trespassed on Yogi Bajan’s ranch to flirt with emu’s and peacocks, jumped in glacier water at 12,000 feet, stayed at an ashram with strangers, bathed in hot springs outside of Taos, soared over my college town in a helicopter, and was greeted with radical hospitality every step of the way. Just writing about those few weeks of ‘transition’ reminds me why I want to keep traveling and making connections with the land and its incredible stewards.

So, here I write, beneath the shadow of the steep Flatirons in my renovated childhood room, now a sophisticated space lined with succulents, candles, yoga gear, and an appropriate desk for a dedicated writer. I have arrived here for a brief visit to unleash the stories in my head and build a sustainable freelance writing career. If you, too, are thinking of taking a dive into something unknown, I say Go! Be mindful along the way and trust that it may take some time for things to form, but you are always your most trusted resource. When things start to fall apart, remember that you can always rebuild. Ask your community for help because starting over is hard, but nothing worth having has ever come easy.


 When to know you might be ready to shift anew

  • A lack of growth within your organization

  • When your salary flatlines and there is no sight of increased compensation

  • A lack of mentorship and support from supervisors / team leaders

  • When there is no space to voice your ideas and intentions and your goals are not a priority for your boss

  • Poor management and lack of efficiency causes you to spend too much time fixing someone else’s mistakes and oversights

  • If you recognize that your skills are not being utilized and your true talents are not put to use

Finding fulfilling work doesn’t mean that none of these won’t exist but when enough of these are checked off in your current role, it may be time to re-analyze your trajectory. I always ask myself: is my energy output equal or less than the energy I am receiving back from the work and the people around me? If you consistently find yourself drained and depleted at the end of each day, getting sick more frequently, not making time for self-care, and not committed to the same vision that your employer has, then it is time. It is always time to take a step back and hit refresh. There is so much out there and I believe it is our human responsibility to follow those urges to climb high above the red sandstone spires and look for the path less traveled.

Cathedral Mountain, Sedona AZ.

Cathedral Mountain, Sedona AZ.

My journey is not a reaction to distaste. It is a reaction to an observable trend: human beings amass comfort and minimize risk as they age. I get it. I can see the value in that. But both of those things have a tendency to diminish character. I have enjoyed living my life in dynamic seasons, and I intend to continue that. It is a choice to look squarely at the decisions we all feel like we have to make and the priorities we all forget.
— Jed Jenkins