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Writer's pictureAlexander Bertoni

Jumping Into the Abyss: Six Things I've Learned in My First Six Months Running a Brand Content Consultancy

My journey into self-employment as Tulpamancer was sparked by realizations about my own needs, as learned through the harsh teacher that is the COVID-19 pandemic, as well as by an act of radical transparency.

Libby Connolly, a designer that I had met through mutual connections, had written an article about her first three years as a freelance brand designer. She shared revenue numbers, hours worked, and a month-by-month breakdown of major milestones. She also shared a look into the, at times, crippling self-doubt that defines most of the creatives I've met.


It was a startling act of generosity in an industry that so clearly incentivizes creatives to obscure their finances and compete at all costs with their peers. I read that article and knew that now was the time to make the jump that I had been considering for years.



Like many others, the COVID-19 pandemic had given me plenty of time to examine the life I had built for myself over the past ten years and to consider what the next ten looked like. I assessed at the opportunities I had taken, the goals I had set, the ladders I had elected to climb. In doing so, I realized these weren't inevitabilities: they were choices I had made.


The big question I was asking myself was "why did I make these choices, and were they serving my needs?"


On paper, I had accomplished more than I ever thought possible. After graduating into the Great Recession, I vividly remember the creeping dread I felt when stepping out into a bleak hiring environment: I remember the hundreds of applications and the millions of crickets I heard in response; I remember the dark economic outlook; even more, I remember the reality of having moved back to my home state of Maine and needing to live with a parent while I came up with a roadmap for the rest of my life.

At least, that's how it felt.


Through good fortune and passion for the work I considered myself privileged to do, I found myself on a path defined by 3% merit increases, 50% pay bumps attained job hopping, and lots and lots and lots of cubicles. That's to say nothing of the dystopian open concept work spaces. To have grown into a Director of Marketing role in my 30s simply did not seem feasible to someone who, at 22, was just hoping for a role that paid $40,000 a year.


While I was now in the leadership role I had, at least theoretically, wanted and was making a salary I could never have dreamed of as an English major, I also found myself on the road nearly two weeks a month. I answered emails in bed at 7 a.m. and fielded West Coast Zoom calls until 7 P.M. that same evening, scraping out meager hours of time with my fiancée in between the chaos.


My work had become endless "touch bases" and performance and development conversations with members of my team who had challenges that, despite my title, I was given little power to solve. And my time outside of work was increasingly encroached upon by the endless demands of an always-on work culture that I had let myself be sucked into.


I wasn't happy simply managing, I wanted to make things again. I wanted to spend quality time with my now-wife without pulling out my phone, more out of habit than need, to check my emails for the latest fire drill.


I wanted to be the beneficiary of the value of my labor.


So, I took the jump filled with equal parts terror and excitement. In only six months the satisfaction I've found and the things I have learned have helped me grow not just as a professional, but as a human being. In the same spirit of transparency that I'm sure Libby felt when drafting her three year retrospective (an effort I want to undertake, once I have some trends established), I thought it would be helpful to explain six of the most important things I've learned in my budding entrepreneurial journey


The Work Will Come in Waves

After a decade in corporate America, I had become accustomed to being too busy for 50-60 hours per week. Whether it was endless meetings, projects stacked on top of projects, increased scopes of work in the face of layoffs and restructurings, I was under-prepared for the natural inhale-exhale cadence of freelance work.


There is a discomfort with downtime that is ingrained by modern working culture. It will take you time to unlearn that and embrace what life feels like again.


February was a down month for me after an incredibly schedule through the New Year, and that felt scary. What will my next project be? Do I have anything in the pipeline? How do I even get leads? What if people said they liked the work but will never work with me again?


You know, classic neurotic millennial stuff.


But now, I've got five proposals out the door. Hopefully some of them will convert, but you never know. So I'm taking the downtime and using it ways that help me recharge, to be more creative, and to be present in my real life outside of work. I'm reading a lot (check out Monstrilio, I bet it'll be my book of the year), I went to Florida to grab some sun and spend quality time with loved ones, and I'm working on building out an organic content strategy for my own business (you're reading a piece of it!)


All I'm saying is learn to embrace a new cadence.

Niche Down in Public, Take Whatever Comes Your Way in Private

Call in Every Favor You've Ever Earned

Find Mentors and Take Every Bit of Advice

You're Not Just in the Creative Business, You're in the Customer Service Business

Get an Accountant and Tax Person ASAP


It's been an incredible and trying and joyous and scary six months as Tulpamancer, but taking that leap has also been the absolute right decision for my mental health, my career, and my general satisfaction.


I'll end by saying this is not a hardscrabble, pull yourself up by your bootstraps story. There's a lot of luck involved, a lot of privilege, and a lot of serendipity that made this journey possible. But it was also enabled by passion and hard work on my end and tireless support from friends, family, and colleagues. I'd like to give a big and enunciated thank you to everyone who has helped me get this far and to everyone who will be a part of this journey into the future.

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