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Unexpected Lessons from Unintentionally Starting a Business

From a personal Tumblr to an LLC

In August 2014, I was working as creative director of branded content at a large millennial-focused website that I had been a part of for more than three years. It was the kind of place where I could write anything—I had spent my first two years as a staff writer, which often meant writing four original pieces of my choosing for the site per day. But that freedom often left me feeling like I couldn’t write anything. Many people dream of jobs where they can work without boundaries or rules, but having total creative discretion (first on content, then on branded work) made me crave the opportunity to carve out a space of my own, where I could write about one subject, diving deep instead of constantly skimming the surface.

So, that’s when I launched a personal Tumblr to track my budget and discuss money, which I called the Financial Diet (TFD).

As someone who had always been particularly bad with money, and having found that millennial-focused websites tended to talk about everything (including graphic sex) before they talk about finances, it felt like the perfect topic to explore. Even though it was a public Tumblr I had already shared with my followers, it felt private and sacred—a little writing oasis. And on day three, art director Lauren Ver Hage cold-emailed me from the desk of her ad agency to tell me she loved my writing, loved the idea of the blog, and wanted to design it for me. Within a month, we were actively working on the project. Within six months, both of us had quit our jobs to pursue TFD full-time (migrating it to WordPress in the process). And in less than three years, we have become a bustling little team of five women.

During that time, Lauren and I have navigated both the complexities of being close friends and business partners, as well as the frustratingly underexamined process of building a business you didn’t quite intend to start. We happened to go from a Tumblr to a business, but yours might be any product, service, or activity you already happen to be engaging in. In the interest of perhaps helping others who are considering taking something from hobby to profession, Lauren and I want to share some of the unique lessons we’ve learned in building our business together.

Here, in no particular order, are six unexpected things we learned while turning a Tumblr into a viable small business.

1. You Have to Redefine What It Means to Be an Entrepreneur

When you don’t set out to be a business owner but at some point find yourself filing LLCs, meeting with accountants, and thinking about sales goals, the path is deeply, maddeningly unclear. Beyond a general unfamiliarity with the world of business ownership, when you unintentionally starts a business, there is the pressing, almost-existential problem of not being the entrepreneur type.

Lauren and I often share what one might loosely call CEO-bro articles with one another: tone-deaf screeds on the profound personal joy of waking up at 4 a.m. to answer emails or holding six-person conference calls from the venue lobby of a wedding they’re attending. There is this omnipresent cultural idea of what (and who) an entrepreneur is, reinforced by a sort of arms race made necessary by the loftiness of venture capitalism, as well as the tendency of startup leaders to think themselves prophets. Entrepreneurs have oddly become their own genre of self-help guru, dispensing general life advice in the face of the deep irony that most of them have no discernible work-life balance.

Lauren and I have never felt this desire, never considered waking up at 5 a.m. to tackle projects or beat competitors, never aspired to a life where the growth of our company was more important than the growth of our personal happiness. And this has meant redefining entrepreneur for ourselves and actively deciding that there is no one personality type we must aspire to or path we must follow for us to take pride in what we do.

2. You Must Resist the Temptation to Replace Validation with Ego

One of the fundamental causes, in my view, of the entrepreneur-as-guru phenomenon, is a very simple, emotional one: Entrepreneurs as a rule do not have bosses—clients don’t count—and therefore don’t have any of the normal professional channels of validation and recognition. They don’t have an established structure to succeed within, no boss to congratulate them, no regular raises or promotions or tangible ways in which they have moved up a notch on an easy-to-understand ladder. Particularly in businesses that are difficult for the average person to understand, this lack of validation and structured accomplishment can almost immediately incite the need for an inflated personal ego or defensiveness.

For example, we work in digital media, and our company began as a dinky personal Tumblr—something anyone can start. Even in our greatest moments of success — a substantial campaign, a high-traffic month, a project in a new medium — conveying that excitement and receiving that validation to anyone outside of our team is nearly impossible. Most people frankly do not understand what we do — nor how we monetize it — and never will. And this leaves you itching to want to overcompensate, to explain, even to condescend. There have been times when we felt frustrated or even insecure around friends, family, and industry peers who mean well but don’t understand what we do. Learning to be okay with not everyone understanding and not having those normal channels of professional feedback was a much bigger hurdle than expected.

By strengthening our relationships as a team and seeking out more personally rewarding projects, we’ve found that it’s possible to recreate that professional validation without the aid of a boss. (You don’t need to wait for the company Christmas party to break out a bottle of champagne for the good times.)

3. Your Biggest Challenge Will Be Limiting Your Challenges

Growing TFD for the first six months was an extremely linear process: move from Tumblr to WordPress, populate the site with ads, create a substantial amount of content, open all the social channels, and legally establish ourselves as a business. It was a small mountain of mostly tedious work that lulled us into the false sense of confidence many small-business owners experience. It’s not “I can handle my challenges,” but rather, “I know what my challenges are.”

The truth is that as a totally bootstrapped, extremely tight team of five doing everything from backend work to sales pitches to editorial, it’s incredibly easy to get lost in doing a million things at once as we grow every day. As your business expands and the next steps are inherently less clear (and the need to do more things at once increases), your biggest pitfall is likely to be doing a bit of everything and none of it well. When there’s nobody directly above you to tell you what tasks to prioritize — nor, often, a clear way to know up-front exactly how long something will take or the ROI it will yield — it’s easy to lose entire days, or even years, on the wrong projects. And even if you do get a clear idea of the specific things you need to accomplish, not learning early how to create boundaries and say no to taking on more will almost ensure you spend time feeling like you’re treading water, and badly.

To combat this, we create shared documents that allow us all to see the various projects being worked on across the brand and determine where time is being sucked and results are not being delivered. This transparency in how we spend our time has meant that a) other team members know when we are busy, and b) the ROI of our work is easier to evaluate.

4. You Have to Learn Early to Resist Comparison

Our sales manager and I worked together at a previous job in which the scale, context, and goals for our work were vastly different. In the first year or so of working on TFD, we naturally wanted to transfer those same skills and ideas and somehow fit ourselves within them.

But every company is different, and while there are certainly some apt comparisons, they are a) rarely the most appropriate ones, just the ones you are most familiar with, and b) not a useful gauge in the long run. You have no way of knowing another company’s resources upon founding, or its business model, or even how well it’s actually doing. The only valid comparison to make is between you and you six months ago.

The more you can tune out the unimportant comings and goings and the irrelevant metrics of your competitors, the easier it will be to do the work that is best for you. The line between “staying on top of what’s happening in my industry” and “obsessing over how I fit into it compared to others” is fine and maddening. You’re almost guaranteed to do your best work when you’re focusing on your individual needs and resources and not constantly looking over your shoulder.

5. Your Communication Style Is Not the Best One

One of the most frustrating pitfalls of entrepreneurship is this tendency to believe that because a person founded something, their model must naturally be the one your company follows on everything, including relatively arbitrary things like communication style. Having a good idea or the ability to get it off the ground means almost nothing about a person as a leader, manager, or any kind of professional role model.

We’ve all probably seen more CEOs than not who should never be allowed near a group email, let alone a microphone for a press interview. And yet a distinct communication style is often the quickest habit to slip into when it comes to creating a culture: If the founder prefers short, confrontational interaction — well, that’s what you’re gonna get. Failing to understand that some of the best, most talented people may have a completely different way of getting their ideas across means missing a ton of those ideas, if not losing that person entirely.

Doing one’s best to create a neutral, accommodating, flexible style of communication where everyone can feel heard and understood is an underrated key to making every other aspect of building your company much easier.

6. Your Business Goals Should Follow Your Life, Not the Other Way Around

When I started a Tumblr, it was for a clear and distinct purpose: to give myself a creative outlet that also helped improve part of my overall life (in this case, my finances). It was never intended to be a professional thing. Maybe because of that, it’s always been easy to contextualize within the rest of my life. Ultimately, centering our goals as a company around the greater goals of our lives—our happiness, freedom, creative scope, and fulfillment—means feeling happy for what we have and not constantly yearning for something we don’t.

Too often, the company becomes its own life that must be fed and followed, almost always at the expense of its owners. But when you focus first and foremost on what your life should look like, including the company as one element of the whole, the goals and benchmarks for your work become incredibly clear.

In my case, drawing a regular paycheck and simultaneously enjoying the freedoms and creative fulfillment that owning my own small business provides are more than enough. Yes, there is always the potential for the company to grow beyond that, but my fundamental goal of living a balanced, happy life will not. And in focusing on my life as a whole, I’ve stopped myself from chasing the unattainable, burnout-inducing goals that plague digital media—and entrepreneurs in general.

Perhaps it’s a flaw not to wish to change the world in some remarkable way or to go down in history. But I would argue that you create a much happier, more balanced life when you let go of those goals and simply do good, sustainable work.

Because if we take away all the inflated entrepreneur pseudo-philosophy and just be honest here, you can always get another job.

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