Personal Lessons From the First 6 Months of Freelancing

February 2020, Black History Month, marked 6 months since I left the agency life and started my own company. Here are a few things I’ve learned about myself since becoming an Independent strategist.

The 9 to 5 Work Day Should be Reconsidered.

I keep reading thought pieces about how the office is dead and how working from home is the future of work-spaces. Although I love (and I mean love) working from home, I’ve found that the reasons often listed for this trend don’t always include one key element that I’ve found myself questioning lately: the entire socially constructed time-frame of the work day. Not only does it no longer seem to apply to my working style but, once I began to interrogate it further, I realized that striving to fit my life into a 9 to 5 cycle has actually been a life-long struggle.

I grew up in a military family. Being on time, up and early and ready to go has been drilled into me since birth. When you’re a child, you do what you’re told, and this is how my mom and my dad ran each of their households (except my father was more of a terrifying drill sergeant) and I was a good kid, so I always followed orders. I didn’t know it then, but this lifestyle- being told what to do, where to go, how to be and needing permission to do anything would be the start of my quiet rebellion against authority figures and mandated working systems (if only my elementary school teachers knew how much I resented them for needing to get permission to use the bathroom). I did know however that my mom’s dull uniform and signature ponytail was not a future I envisioned for myself as I imagined myself pretty suits and elaborate hairstyles. Needless to say, the military was not for me.

Despite my mother serving twenty years in the Army, she had an uncanny knack for always being late for just about everything. The day she missed my Middle School performance as 2nd chair in an all District band concert was the day I finally broke down and released her of her motherly attendance duties. She was raising twins on her own and working full-time with an undiagnosed case of sleep apnea- I realized i had to pick my battles. From that day on, I vowed to always be on time and for the most part, that’s how i am today (my friends hate me for it). Timeliness is a key characteristic I honor and cherish, but when it comes to showing up to certain things in the morning, my mother’s genes seem to inevitably prevail.

My Sophomore year in undergrad, one of my prerequisite classes was a biology class in a building that was directly across from my dorm. It was, to date, one of the earliest classes I’d ever have in undergrad and it started at 9:30am (I can feel you judging me). It was also a class that started one of the longest days of my week as I wouldn’t be back to my dorm until well after 6:30pm.

Needless to say, I was always 10–12 minutes late for that class every week and would secretly hope I wasn’t being penalized for it. It’s not that I didn’t try to get there on time- my morning routine would just be longer than I’d anticipate. One day I came in right as the professor was calling my name to mark my attendance. She didn’t see me walk in but I heard her stop after she called my name and say “… Oh she’ll be here soon”. She was right. I was in every class, and a generally good, highly participatory student. I just couldn’t get to my seat on time no matter how much I tried. I was grateful for our unspoken understanding and I still am today. This was when I learned the value of being good at the things I was late for as my tardiness would often be overlooked because of it.

I’d continue to avoid classes before 10am for the rest of my time in undergrad and thankfully for me, I found ways for that formula to work in my favor. This pattern however, definitely continued into my work life.

One day, the new Managing Director, who had been tasked with turning around the business and lifting office morale, approached me to talk about my timeliness. I had been consistently showing up to the office between 9:45 and 10:15am (9:45 was a good day as far as I was concerned) and she wanted the entire office to make it in by 9am, something that seemed feasible to her — a boss, mother and wife who would often be at her desk by 8am. So what the hell was my excuse?

I remember stuttering in disbelief when she told me this- how on earth would I manage such a task? She was a boss that I loved, and I wanted to be able to appease, but I knew deep down this would require a huge shift that I wasn’t sure I’d be successful at. I told her I’d try my best to get there by 9:30am and she hesitantly agreed to this deal. Although I kept up the early arrival time at first, I eventually reverted to my previous ways, especially as I began to take on grad school full-time and work full-time.

Despite my inability to get to work in the time-slot she preferred, I was one of the company’s best workers, I never left early, and never left my desk for lunch breaks (the “designated lunch time” is also something I’ve never really agreed with- why do we eat lunch so early?). This, in my mind, was the necessary exchange for me being in my seat later than desired. I’d just work with my head down until 7pm -8pm at night, and it was something I did willingly because it came much more naturally to me.

My next role in a different company allowed me a a lot more freedom and flexibility, the likes of which I had never had before. More than that, it was in this role that I learned that I could actually do work early in the morning- it just needed to be from home, in my pajamas, in the comfort of my very warm, climate controlled living-room. I found that my most productive days would be when I’d role out of bed and hop on my computer and easily crush a 10–12 hour work day.

All of these experiences taught me that the 9–5 in-office work schedule is not one that produces the most optimal outputs for everyone — especially me. In fact, I’ve realized that it actually reduced my creative outputs and productivity.

Today, as an independent strategist, I find that the ability to work in time-slots regulated by me not only enables me to live a more fulfilling and therefore enjoyable life (ie: morning workouts at reasonable times), but it also enables me to get work done in the most efficient way possible. Whether I start the day at 7am or 11am I’ve been able to successfully dictate how to best spend my time in ways that I know will truly benefit me.

I’m not saying the entire system should be thrown out- I do feel a structured time-frame is necessary especially for younger work-force members who are just starting out and just beginning to understand adulthood. But I do hope that “offices” and “work schedules” of the future begin to have sliding start times for those of us who might work better from 10:30- 6:30 or from 12pm to 8pm.

I am a Strategist Who Happens to be Black

I am a researcher & brand strategist who specializes in cultural insights & semiotics- and i just so happen to be Black. Why do I bring this up? Since becoming an independent strategist I’ve learned that due to my race, I am ten times more likely to be approached for multicultural projects despite having 9 years of experience in categories that primarily haven’t always centered on multicultural consumers.

Let’s pause here for a second because I do want to point out that this is an entirely new phenomenon due mostly to recent cultural shifts in business requiring brands to get diversity and inclusion right. D&I and marketing to multicultural audiences has become new mandates within a lot of the brands I work with and marketers are simply trying to get it right. As a Black strategist who has led a business unit in this space, it is an area that I am well experienced in academically and professionally- but it is not all that I am.

A quick semiotic lesson:

The meanings for the word “culture” are evolving. In the past, it automatically signaled the idea of “ethnic” or “multicultural” or “non-white”. Today, the meaning of the word has broadened beyond race and in the brand strategy world, companies that dial into cultural intelligence or cultural insights are doing so to ensure cultural relevancy as a whole. But the practice of cultural insights is till new in the US, so often, when prospective partners learn that I am a cultural strategist and see some of my past experiences across brand strategy, multicultural strategy and cultural strategy, I am sometimes automatically positioned as a multicultural expert ONLY despite being knowledgeable on a myriad of topics and categories for all audiences.

In an interview with a potential agency partner late last year, I was asked why multicultural work was not my main passion area. The truth is race work can be as emotionally draining as it is fulfilling. While on one hand I get to bring to life the stories & experiences of people who are often overlooked, n the other hand having to explain to boards of people who don’t look like me that Black and Brown consumers are people too can be very deflating.

This is especially true as the main attraction to what I do is my ability to learn about new topics and categories and how they are shaped and evolving overtime. From luxury and retail to health and well-being, I am genuinely interested in the opportunity to work on things where race is not always the main topic (don’t worry, the topic always makes an appearance- it has to in today’s shifting demographic landscape). More than that, my ability to switch in and out of general market and multicultural spaces makes me an even stronger, more well-rounded strategist in general as culture and insights don’t happen in a vacuum or within a designated “general market” or “Multicultural” buckets as these audiences are always impacting each other. Having the ability to knowledgeably step into both spaces effortlessly is something i pride myself on.

I love that multicultural & diversity projects have are having a moment- we are well overdue for this. However, I often refer to the process of solely working on multicultural projects as eating too much cake: it can be too sweet, too decadent, too rich, and therefore nauseating & headache inducing at times, but it’s still nice to indulge every now and them. As I continue to build my portfolio with these really great meaty projects, I’m hoping to have more “well-balanced meals” in the work that I do as I continue to explore this new career chapter.

I am Exactly Who I Thought I Was

For the past 9.5 years, I’ve worked pretty tirelessly in building a pretty solid reputation for putting in the time and going above and beyond allocated hours to get a project 100% right. I’m meticulous about the insights I find, but more than anything, I’m always working to ensure that the work I do is actually additive for my clients, and most importantly, impactful to their bottom line. In short- I love this shit.

I was told once by a very senior colleague that I “didn’t have to work so hard” and that I “didn’t have to always make everything I did so ‘perfect’”. I remember feeling shocked and enraged by this statement, but also somewhat unsurprised. Who, champions mediocrity? More than that, how could I, a Black woman, ever think to have such a privilege of being mediocre and still being seen as fully capable? It was a logic that went against everything I’d been taught about adulthood and advancing in my career.

When I spoke to a (very dear) career coach about this, she asked me “why do you think you feel the need to work so hard?”. Without even blinking an eye, I said “because I know one day I’m going to be in a position to work with clients in my own business and because of this, my reputation for the quality of my work is always on the line…anything with my name or my face on it must always be stellar, and above par”. A few weeks later I was starting my own company and jumping into the deep end of working for myself.

Getting to this point though- a point where I believed enough in myself and what I had to offer enough to do what I love outside of an agency took several years of convincing by outside forces. My parents, who barely finished high school themselves, didn’t have the blueprints for how to navigate & master corporate spaces- I’ve had to mostly figure all of this out on my own. Thankfully, my mom & dad’s ability to survive any and all circumstances (literally) is in my blood as, not only have I been successful in the corporate world, but I’ve also managed to create a unique space for me to do what I love on my own and for myself.

Since then, I’ve learned that my 9.5 years of overworking, and going above and beyond has paid off, as my past clients & contacts have sought me out & referred me to new clients since starting my own company. I’ve also learned that I’m actually pretty good at this business running thing. Learning the ins and outs of how a business functions (and actually utilizing my business admin & marketing minor) has been more fulfilling that I would have ever thought.

I’m not sure how long this ride will last- it hasn’t even been a year yet, but I’m loving every aspect of this new career chapter so far. From speaking with new clients, connecting with other freelancers, and creating a brand that directly communicates what I do and how I do it all of it has really been a joy. Additionally, despite the reasons that caused me to leave my previous companies (a story for another time) I’ve successfully managed to maintain strong connections with my past employers who are now my partners.

None of this has been done without fear, but all of it has been accomplished through faith, and I’m thankful enough to say that I’ve been blessed to experience a range of projects so far and I can’t wait to see what else is in store for a Touch of Whit Creative.

Stay tuned :).

Whit