6 lessons I learned from a year of self-employment with own “agency”
It was over a year ago now that I decided to venture back into that great unknown that we call self employment. I am the founder of my own “agency,” Narrate Creative. The quotation marks are because it’s just me, an agency of one. I do content strategy and content management for brands, usually as a subcontractor or partner with other agencies.
To say that it has been an easy year would be a massive lie, but one cannot expect anything to be easy when taking the entrepreneurial route. Perhaps if I share some of my own challenges and wins, it will help others prepare for dealing with their own. Being your own boss really is better, it’s just not easy. There are a few specific things I’ve learned that are worth sharing. Here’s the list so far.
1. Finding work that you love is hard. You might as well work for yourself
This isn’t true for everyone, but it is for certain personality types. Maybe I’m answering some call to be an entrepreneur that is beyond my control. I don’t know. I’m not unemployable, like some entrepreneurs like to joke that they are. In the right circumstances, I’ve been a great employee on a number of occasions. I just can’t stay in one place for too long. And I prefer to call the shots whenever I can.
After 25 years of employed life, I know this about myself: I prefer “creative” work, and the circumstances to be creative have to be just right for me to thrive. It’s difficult to start my own business, sell myself, be my own personal assistant and bookkeeper and of course deliver high value to my clients, which is the point of it all. But even with all the challenges, it’s still the easiest way to make sure that I’m in the right circumstances, doing the kind of work that I enjoy and I am best at. It also affords me a certain amount of variety. Most of my client engagements last 3–6 months. That means there are always new faces, new challenges and new problems to solve. Since I’m the boss, I have a certain amount of control over who those faces belong to, and what challenges I get to work on solving.
2. It’s easier the third time, but only eventually
I’ve been through this before. Twice before in fact- and had to return to the “stability” of employed life. Read on to hear more about challenges with cashflow to learn all you need to know about why the first two times didn’t work. Business is competitive. It’s different this time though. I joke that my hair is greyer, and therefore people trust me better. That might be part of it. But the truth is, things really are different. I was pretty sure I knew what I was doing in the previous two attempts at starting my own agency. “Pretty sure” doesn’t cut it in this game. Now, I speak with a certain level of conviction because I DO know what I’m doing. I’ve been doing this a long time. That experience means I have an anecdote for most of the problems or challenges my clients are facing, and I can see a path to success for them that is within their reach. That wasn’t always the case.
3. They don’t call it “the burden of proof” for nothing.
Before you can consult and advise, you gotta prove you know your stuff. The best career advice I can give anyone, based on my experience, is to get on a winning team before you try going it alone. I have toiled away in the trenches with bootstrapped tech startups, and I have helped lead the charge with a software company experiencing hypergrowth. Both make me ably qualified to solve problems for other tech companies and brands, but only one sells new business. Until you’ve ridden that rocketship of success, you’ll always be climbing an uphill battle when you’re selling yourself. You’ll be speculating about how well your ideas work, rather than having experienced the successes and failures of spending budget at scale. Not to mention hiring, managing, planning and producing, all at top speed.
“This is Jordan. He used to run the blog and social media for Hootsuite.” It certainly opens doors for me, I’ll be the first to admit. I don’t mean to be blowing smoke up my own ass; there is a massive amount of value in being part of a winning team. People want to hear what I have to say because I worked alongside some of the brightest minds in the business, we kicked some serious ass, and we learned a metric crap-ton off one another. I have yet to see the full extent of the value in that, and I cannot overstate it. Not just my ten years of tech industry experience, but above all my 1.5 dog years of experience at Hootsuite, is my proof. In a year and half, we doubled the user base from 4M to 8M, rolled out an Enterprise product and started snaring market-share globally. Ask me about it — I love telling stories. Now of course, my client projects and their outcomes are their own form of proof, but I would never have a chance to accomplish those things if I didn’t sell first.
4. Cashflow is hard. Like really, really hard.
A friend, who I also consider a mentor, Darren Barefoot said it best when I was picking his brain about my decision to go it alone again. “The first year will be the hardest,” he told me as we lunched in Yaletown. I’ve repeated that advice to others since — as much for my own benefit in hearing it aloud again, as for theirs. Most advisors will tell you you need about six months of “runway” or cash, if you like, to survive starting a business. That was mostly true in my case; it took five months before I started generating revenue. Now that I am cashing checks, I’m at the mercy of my own ability to invoice and collect, and in some cases to ride out the payment terms of larger clients. I even had a most unfortunately timed run-in with a non-payer, a lesson that ended up being worth more than the lost income. I’ve moved away from dealing with early-stage startups, especially the pre-revenue variety, to insulate myself from some of the risk that I’m exposed to as a sole proprietor. If you can solve your cashflow problem as an agency, you will be able to focus much better (with much less stress) on the rest of the tasks at hand. Easier said than done. I scaled my expenses back to a trickle, and relied on credit, and the help of family members to ride out the dark times, but in the end it was worth it.
5. Working alone is different, but possible
When I decided to restart my business for the third time, I had to send a few ripples through my network to try to generate some referrals and leads. Initially I thought I’d be better off working with a partner, but ultimately found that focussing only on what I was good at and what I could sell was the way to go.
It’s a lonely pursuit though man, let me tell you. Emailing friends, agency and startup founders, investors, former colleagues (some of whom I hadn’t spoken with in years), all in the hopes of getting a meeting was an uphill battle and was often more depressing than promising. I needed something to happen, and that didn’t help my confidence as I “sold” myself.
And then, just as I was ready to throw in the towel, as the last of my resources was about to dry up and require that I return to the job market, someone took a chance on me. It was almost fateful. Not just someone, but the outstanding Mack Hardy, owner and founder of Affinity Bridge. Mack was seeking a branding and content strategy in advance of building a new agency site, and wanted my help to prepare it. Not only did this mean I was earning again, but it was a tremendous boost of confidence and created a new “product” line for Narrate Creative: I have since helped three other agencies with their internal redesigns or rebranding.
Most of the time though, I toil away in solitude, plugging away at this keyboard like I am now, alternating between a standing desk and having my feet up on the couch; pants optional.
But the business benefits and inspiration from working with such a cool and world-changing web development agency was just the start. I told Mack about my struggles with getting started (as an agency founder, he could certainly relate) and he gave me the best piece of advice I’ve received about agency work, when he loaned me his copy of “The Win Without Pitching Manifesto,” by Blair Enns. I recalled that Darren Barefoot had also recommended it, so I started reading it that very evening, and it was a game-changer, to put it mildly. If you own, work at or are thinking of starting a creative agency of any kind, buy this book right away; I assure you it will pay itself off. I learned how to sell myself better, how to place a high value on my work, and how to better ensure that I can work with the kind of clients I love. I will be eternally grateful to Mack, Darren and Mr. Enns for the pearls of wisdom gleaned from those pages.
Since working with Mack and his team, I’ve had the pleasure of working with my good friend Jesse Korzan and his partners at EUX in Squamish on several projects that I am very proud of, some of which are still under wraps. I’ve also worked on several projects with the delightful and wicked smart team at Modern Craft, an agency that focuses on digital strategy. They have become the ideal partner, in that they focus on strategic client engagements, and need subcontractors like myself to help with specific tactics like content strategy and content management to put plans into action. By making the decision to work primarily with agencies, I get access to their brilliant minds and resources, and they become pipelines of new work to keep my appointment book full. I love, LOVE working with these people, and visits to their respective offices are the highlight of my work week. Most of the time though, I toil away in solitude, plugging away at this keyboard, alternating between a standing desk and having my feet up on the couch; pants optional. My bookkeeper is sub-par, my barista is not bad (he makes a rather delicious cappuccino, in fact), and my salesman has a pretty good record. And I don’t even have to write them a Christmas card this year because they are all me.
6. The “put yourself first” rhetoric? It isn’t rhetoric after all
Of all of the personal breakthroughs I’ve had in the past several years, this one has been the hardest to overcome. Maybe you won’t be surprised to know that it wasn’t until I started taking that advice seriously and doing something about it that I saw any amount of success in my business.
I have always told myself and others I chose to work myself to give me the flexibility to be around for my kids; the various pickups and dropoffs, pageants, dance performances and the like. But now I realize the benefits to me as well, and I make that part of my focus so I can keep me eyes on the prize, stay healthy and reduce stress.
One of the things I enjoy the most in this world is riding a bicycle. I’ve said many times how it is my excercise, my social life and my therapy, all in one. The first time I got on my bike at 3pm on a sunny weekday, just to go for a ride, it felt indulgent. Knocking off of work to go for a two hour bike ride is not a common practice in normal office life, so it came with a certain amount of guilt, going out and enjoying myself when I could be at my desk. But I learned something on those first few rides that has become a cornerstone of my ethos. That riding a bike not only gives me a good deal of energy and vitality in terms of physical health, but it also opens my mind and lets me focus on my work. Almost half of my “work” is spent conceiving ideas. Not typing, not sketching, not building Keynote decks (though that’s the next biggest task), not talking or doing anything other than thinking through a problem. Whether it’s preparing a proposal, or thinking of ways to solve a client problem as part of a strategy, taking a break away from my computer and giving my mind the freedom to wander has paid serious dividends. I have stopped my bike on solo rides to jot notes into my phone that have become the nexus of a client plan, where it might have taken my several more hours of distracted thought to “see the light” and get the right idea.
The bike has now become an obsession: I purchased another new one, won a voting contest with Canadian Cycling Magazine and Castelli that took me to Italy for the most epic gran fondo I will probably ever participate in, and I am even thinking about racing again. At 39 years old. Putting myself first has resulted in a better version of myself, which is the best thing I could do for my kids anyhow.
How’s it going?
It’s the question that I get the most. “How’s business?” everyone wants to know. These days, I can look them square in the eye, smile and say, with a certain amount of conviction, “Good! I have no complaints, only gratitude.” And then, both for clarity and my own catharsis, I add, “It wasn’t easy though. It took some hustle and some hard times, but things are in a really good place now.”
And it feels really good to say it.
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