The Career Advice I'd Give My Younger Self

The Workplace Lessons I Learned Too Late

DD4 at Entry-Level Work: LinkedIn, Mountain View, California, 2014

This post is part of a 3-part series between DD4 at Work, First Gen Rising, and Reframed; an experiment where former colleagues reflect on what we wish we knew earlier in our professional journeys. Our responses reveal how differently individual perspectives can be shaped by the same systems, how unwritten rules influence tangible outcomes, and how practicing self-advocacy can make or break a career.

Here’s some of what I wish I knew back then, presented in Q&A format.

1. Was there a moment where you played it safe and you know you should’ve taken the risk? What was at stake?

I am infamously risk-averse. I have Obsessive-Compulsive Disorder (OCD); it comes with the territory. Other than going to work for startups, I’ve tried to play it safe as a rule, meaning there have been moments I’ve chosen the comfort of security over the uncertainty of change. I turned down the opportunity to interview for a promotion in 2016, feeling like a teammate was a better fit for a newly-scoped managerial position. I thought my chance would come eventually, that it’d be better to demonstrate humility by stepping back to let someone else shine.

Today, I’d coach a client to go for the promotion. Hindsight taught me something simple: you’ll meet many who’ll try to limit your progress; don’t be one of them. Shoot your shot.

2. What’s one skill you wish you’d started building 5 years earlier? Why does it matter now?

Self-advocacy is one of the most important skills in a professional’s toolkit, and it took me far too long to learn.

As an openly gay Black man, I’m used to the role of outlier. There aren’t many of us in corporate spaces; the resulting blend of hyper-visibility and statistical rarity shaped my work. I felt the burden of representation acutely; overthinking, overcompensating, and overachieving on a near-constant basis. If I wasn’t objectively “the best,” I’d make it harder for other Black and/or LGBTQ+ talent to be taken seriously, so I became the best. I also became routinely passed over for development opportunities by colleagues with weaker performance, but stronger self-promotional skills.

They may not have been able to produce at my level, but they had what I lacked: the ability to talk about themselves openly, to trumpet their accomplishments, to emphasize visibility instead of competence, and to identify stakeholders who could influence outcomes on their behalf, regardless of merit.

As Ashley puts it, “Work doesn’t talk, so you have to.”

3. What did you have to unlearn that nobody warned you about?

Keeping with the theme of self-advocacy and professional confidence, I went into my career thinking performance was King. I thought that if I surpassed metrics, took on stretch projects, smiled, nodded, kept my head down, and steeled myself against inevitable microaggressions, I’d succeed. I’d be promoted. I’d make more money. I’d become a leader. I was mistaken. Not entirely, but significantly.

When you’re good at your job, your reward is more work. When you’re a reliable performer, your reward is stability. When you combine performance with political awareness, your reward is undeniability.

4. If you could give your younger self ONE specific piece of tactical advice (not conceptual, an actual “do this”), what would it be?

In “Code Switching at Work is Good, Actually,” I reflected on the standards that influence our sense of professionalism. One of those, especially for those from statistically underrepresented demographics, is grace under fire. We are expected to minimize disparate experiences, to choose passivity over action, and to protect the reputations of our employers, even when they are discriminatory.

At a former employer, I was paid $30,000.00 less than official salary models dictated. As a Team Manager, I was paid less than individual contributors in the same department. My Supervisor, several years my junior, responded when asked that my pay was “Fine where it was,” because she did not believe I was “Loyal enough to her.”

What I should have done was document my experiences, including that conversation, raise my concerns through official channels (reporting my Manager to HR), and potentially, retain counsel. What I actually did was quietly interview elsewhere, accept a higher-paying position, and resign unceremoniously. My Manager likely went on to repeat the same behaviors elsewhere, something I still feel guilty about.

Choosing your battles is important, and not every issue requires official escalation. However, choosing silence when confronted with injustice perpetuates systemic inequalities, squanders talent, and stifles corporate innovation. Know your rights, document everything, and don’t default to graceful silence if something is illegal.

5. What’s a phrase, habit, or mindset shift that changed how you operate at work? Where did it come from?

“Always remember the optics.” Simple, straight, and to the point. The advice came from Catie Brand, my Manager at the time. In a one-on-one meeting, she gave me uncomfortable feedback: a senior leader complained that throughout the day, I seemed to socialize more than work. I was incredulous. I was the #1 performer on Catie’s team, I’d regularly assumed responsibilities outside of my scope, I worked directly with Executives, I’d been promoted. Catie, of course, already knew all of that.

“You’re not in trouble,” she assured me. “I’m your boss; I know how much you do. But people who don’t work with you directly only know what they see, which is you being friendly and talking to everyone. Always remember the optics.”

The feedback stuck. In the corporate world, perception and performance are inextricable. You can do excellent work and still experience disparate outcomes based on any other factors, fairly or not. Always know your audience.

Most of these lessons aren’t taught. They come from experience: gradually, reactively, and later than you’d like. We aim to change that.

The advice you hear from Ashley, Michelle, and me can’t guarantee you success, but it can help you navigate your career with clearer understanding of how things really work. If you know, you know. You know?