What a difference a year makes. Just a little over a year ago, Damon and I signed those final signatures to complete the process to transition into becoming part of The Root. Like most things in life, it’s important to reflect on milestone moments. By this point last year, Damon had begun working as a senior editor at The Root and I was still about a week away from my official start date, while closing up shop on the job that had persisted the previous 14 years of my life (15 for retirement purposes, thank you, lawd).
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1. Looking back, the entire process was surreal. What started (again) as some talks in February 2017 culminated in a finalized business dealing with contracts and legalese at the end of June 2017. It was surreal because it happened, but also how it happened. Almost the entire year of 2017 was full of discussions between Damon and I, and often other entities, talking about what we wanted to do or be and how we could get there.
2017 will go down as a watershed year in my life if only because I left possibly the most stable job I could have to give dreams (with benefits and a salary) a shot by being part of an organization that, for all intents and purposes, was backed by a company with long dough and hopes and dreams. Again, what a difference a year makes. Put a pin in this.
2. Leaving my stable job was pretty anti-climatic. My going-away party was awesome and I cried. I worked with a great group of people and I’ll never take that for granted. My co-workers and my boss, in particular, are what kept me there so long. I cannot understate how important it is to like your co-workers and have a boss that you believe in and who you know has your back. My former boss is a Hall of Famer to me, and that went right up the chain.
I seriously worked for and with a great group of people. Meanwhile, I do not miss the actual job one bit. Not once in the year since I’ve been gone have I yearned for one single part of that job. I think I forgot how to do it all the moment I left, which lets me know that while I had a great job, it wasn’t the job for me, and I never felt like it was, but it always enabled me to do everything that I needed to do to get where I’m going. But yeah, I entirely made the right decision professionally.
3. Going from a structured work situation to one where I have the freedom to make my schedule work for me has been more of a struggle than I anticipated. I’ve had to build structure through consistent work places and time scheduling in order to function properly. The free, “create when you want where you want” (between the hours of 8 and 5:30, of course) life looks awesome, but it takes some adjusting. At this point, I’ve got my routine down, but still.
4. Interestingly, if not surprisingly, constant, creative, content creation is much more laborious when it’s your job than when it’s your side hustle. Doing things for pay means that the expectations are understandably higher. And that’s reasonable, but it also means that creative ruts, something that you can mitigate when it’s your side hustle, are more of a nuisance and can get you called into the principal’s office. That has also been an adjustment.
5. Piggybacking on No. 2, I went from a great group of co-workers in my traditional job to a great group of co-workers and a great boss in my VSB life. There’s nothing like having a great, supportive, creative group of individuals to work with in any capacity; I’m glad that’s the environment we walked into at The Root.
6. Being a part of a huge organization means just that—you’re part of an organization, which means that you can’t just do shit because it’s a good idea. Other people who “OK” things and teams who have to make those things happen within certain rules and regulations must also be on board. There are things that we talked about in our negotiations that we have yet to really do that I’d hoped would be in full swing now. “Patience is a virtue” is real talk.
7. Back to that pin. When we joined up with The Root/Univision in June 2017, the environment seemed like one entirely of growth, potential and opportunity. Not sure if you read the news or not, but for the past several months the company itself has been going through all types of business-related shit: layoffs, restructuring, etc. Now, Gizmodo Media Group, the company under which the editorial platforms like Deadspin, Jezebel, The Root (and VSB amongst others) fall is up for sale. I have no idea what this means in the grand scheme of anything, but this is the first time since 2001, when I graduated from college, that I’ve had any feelings of uncertainty in terms of my career and paycheck.
8. Joining up with The Root was then and still feels now as if it was the best decision professionally and also the right decision. I don’t know what will happen in the next year but I said the same thing in 2016 and here I am.
9. Business. Maaaaan.
10. I’m really curious what life will look like a year from now, after year two of our life here at The Root. If this last year, well, really last two years, has taught me anything, it’s that you should expect the unexpected and be prepared for it all.
Straight From 
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