It’s Time to Get Real About Your Career

Moving from self-shame to self-love

Graduating with a fine arts degree means always having to say you’re sorry. Over and over again. As you encounter questions from friends and loved ones. Strangers and co-workers. You try and explain your field of study. Justify your life choices. While they just shake their heads, looking in the distance. At any possible off-ramp from the conversation.

There’s nobody to hold your hand and help you build a career. You basically have to figure it out on your own. And so when I completed graduate school I had no idea what to do. It was quickly becoming clear to me that I lacked the talent to earn the type of living I desired. And I had no appreciable skills, at least in the eyes of prospective employers. I mean not one. But by some incredible stroke of luck, I happened to be living in Seattle during the Dot.com boom at the turn of the century. When anyone with a pulse could get a job. And a pulse was about all I had going for me.

Somehow I found an employment agency that was willing to take a chance on me. Who knows what they saw in me? I’m pretty sure at least I was punctual. Hopefully I smiled some. But knowing me back then, I doubt it. Anyway, I received a glowing reference from a former arts colleague, and just like that, my career in information technology was born. I remember sitting at my desk the very first day of the first office job I had ever had. I thought to myself, “Ok. I can do this. Maybe even for the next twenty years. I’m going to be ok.” I worked as hard as I knew how to do over the next few weeks and months. And then, slowly but surely, something completely unexpected happened: I realized I was good at it.

I mean really good at it. It all just clicked. I really have no explanation. I guess all those years spent studying classical music paid off: thousands of hours spent practicing scales and etudes, hundreds of performances for all sorts of audiences, all while systematically (even obsessively) analyzing all my strengths and weaknesses. But my secret strengths and untapped talents didn’t end there. All those poems and analytical essays I wrote at university meant I could crank out a position statement like nobody’s business. All those hours spent teaching in the classroom and in private lessons, meant I knew how to break down difficult concepts into bite-sized chunks. It turned out my fine arts degree was my secret weapon!

There was a high applicability in the skills I cultivated as an artist, and the risk analysis skills required of any IT professional. What I had no idea about, and never could have planned, was the surprising confluence of marketing and technology that was just beginning, thanks to the newly tapped powers of the internet. It was the Wild West in those days, and there were no formal training programs. But that left room for folks like me to learn on the fly. The entrance and rise of ecommerce and website technologies meant I was able to learn all sorts of adjacent marketing skills as well. And eventually I carved out a new niche for myself as a marketing technologist. I made my own luck.

Don’t get me wrong. For all the privileges I had going for me (white, male, able-bodied, etc.), I still ran into numerous roadblocks along the way. It pains me to think of all the disappointment, disgust, and disdain I have encountered over the years. Job interviews, where hiring managers or HR personnel flagged me as being gay. Colleagues sensing I wasn’t just like them. As much personal freedom those of us who cannot pass as straight might reap, there is a terror that comes with the thought of not being able to support yourself by virtue of your sexual orientation, gender orientation, or gender expression. And sitting across from a hiring manager sneering while wielding their authority is an abhorrent experience. I often look back and wonder what other leaders in those companies would have thought, had they known what was really going on behind closed doors in those interview rooms. But then again, it was their job to know.

Companies are just collections of people. And people are imperfect. In some cases our flaws are just the innocuous expressions of our human design. But in other cases we have weaponized our shortcomings as a means to make ourselves feel powerful on the backs of others. And many workplaces offer little sanctuary. Sure, nobody wants to think their choices are born of bigotry. But the reality is if there are not people of all races, genders, and sexual orientations at all levels of the company, then diversity is just lip service. And if your company does not explicitly embrace diversity, it does not deserve your talents.

The math is really simple: if your boardroom is exclusively a collection of elderly, straight, white men, then your company is racist, sexist, homophobic, and transphobic. It does not matter your industry or business category. Regardless of your geography or the intentions of your mission. There are no excuses.

Behind the scenes, here’s how homophobic and transphobic bigotry often works:

• Leaders insist they aren’t “prejudiced,” but when a promotion or opportunity rolls around, invariably they just don’t know if you’re ready or “mature” enough (since only heterosexual men can display maturity)
• Leaders claim they are not homophobic, but deny you opportunities because their clients or customers are “old school” (a euphemism for their bigoted beliefs)
• Leaders tell you how “liberal” they are, but fear their company culture is awfully “conservative” (code for you aren’t masculine enough, straight enough, etc.)
• Leaders insist you closet yourself, just so you can put them at ease (refrain from being less than you are, require you to lie, etc.)
• Leaders create corporate values explicitly designed to promote bigotry (often in the guise of religious freedom)

Bigotry is a form of abuse. It is a way to steal money and power from those who happen to belong to some minority, but are equally or more deserving than their peers. Corporate bigotry is often state-sanctioned theft, since many states in the US deny explicit legal protections for LGBTQ+ workers. It is welfare for heterosexuals. A way to shift capital from one group to another. The impacts are often profound and long-lasting. Lost money is rarely recouped in the long run. In the aggregate, those heterosexual workers hired instead of you continue to earn raises, bonuses, and promotions at relatively constant rates. And those of us that could not get our foot in the door continue to fall further and further behind.

These impacts are further exacerbated with the increasing geographic segregation of our country. While more and more coastal states and municipalities enact employment legislation protecting, many states in the center and south of the country are not yet following suit. That creates a fragmented employment fabric across the country. So it falls to workers to advocate for their own best interests, while activists work with legislators to change laws. Not everyone can afford to pick up and move to a state which practices greater equality. But we can all get empowered. We can organize. We can insist for better government representation. We can inform our allies. We can inform those not yet allied with us. But we need not remain victims. If you work for a company that does not value you, it’s time to take stock and consider your options.

Getting empowered starts with being honest about the reality of your situation:

• How much do you have in savings?
• How long will it take you to find a job of similar compensation?
• Can you realistically cut any expenses in the meantime?
• What sort of pay cut can you afford in a new job, if your quality of life improves?
• What are the costs (mental, physical, emotional, spiritual) of remaining in an abusive situation?

These are important questions, but represent emergency-level thinking. By the time you start asking yourself these questions, your job or finances might already be in jeopardy. That’s why it’s important you start a broader assessment before things ever get to this point. Focus on your portable equity (that compensation you can take with you).

There are three main questions to ask yourself in order to evaluate your portable equity:

• What is the quality of opportunities (chance to do great work, learning, advancement, etc.) available to me in this position?
• What is the quality of my professional relationships available to me through this position?
• What is my quality of compensation?
• What is my quality of life?

Your portable equity is larger than your compensation (pay, benefits, etc.). It also includes your quality of life (How many hours do you generally work? How long is your commute? Do you like your colleagues, etc.), all of the professional contacts with whom you interact as part of your job function, as well as the quality of opportunities presented to you (Do you get the plum assignments, are your toiling away in obscurity, or somewhere in the middle?). All things being equal, I always try to spend the bulk of my attention on this last category.

If I can afford to pay my bills and support my family, I keep a keen eye on what I am learning in each opportunity and how it might serve as a lever to lift me to the next opportunity. Such that I can continue to solve problems, build value, learn, and grow. The professional relationships you build are extremely valuable, but I have found other ways to build those. Of course sometimes you just have to turn a buck. But if you have the resources to sustain you, follow the learnings.

Depending on your field of employment, your salary is often just a part of your total compensation, which also often includes various benefits like healthcare benefits (for which you are only partially charged), contribution matches to retirement accounts, and ancillary goodies (cell phone reimbursement, bus passes, etc.). In order to find your work/life balance, you need clear goals. And the trick is our goals are always changing. They change with the seasons of life, accumulated experiences, evolving relationships, and even exigent circumstances. That means evaluating your total compensation as related to your life goals is an important, ongoing meditation:

• Where are you?
• What do you hope to achieve?
• What will it take to get you there?
• Are you in alignment with your core values, mission, and purpose while earning this money?

Your salary alone can be misleading. To consider my quality of pay, I find it useful to calculate my “hourly rate”: your salary divided by the number of hours you work in a year. I generally assume there 2,000 work hours in a year (after subtracting paid time off) but then prefer to add commuting time on top of that. If you are routinely expected to attend office functions and events, make sure to include that time in your calculation as well.

There have been times when I have been given a raise, but my hourly rate declined thanks to all the additional work I took on as part of the agreement. In other cases, I have taken jobs at lower pay if it improved my hourly rate. Just make sure you can to afford the hit to your cash flow. In fact I care so much about my hourly rate, that I have long kept my own time sheet to track it. That ensures I maintain a healthy work/life balance relative to my salary and life goals.

Now that you have landed a job that aligns with your life goals and pays the bills, while allowing you to contribute to savings, you will likely want to do all you can to keep that job. In order to do that, you’ve got to learn your value. Without an accurate assessment of your value, you are likely to narrowcast, operate out of scarcity, and dream small. You value is greater than just your self-esteem. More than just confidence. Though both of those qualities are key to building the career of your dreams. Your value is all that you bring to the table.

For years I under-valued myself by concentrating primarily on switching costs: how painful and expensive would it be for me to change jobs, and how likely would they be able to match my portable equity? This meant I frequently thought I was over-compensated and under-utilized. And when seen through the lens of switching costs, that was certainly true.

It was not until I learned to evaluate my performance through my employer’s eyes that I gained the confidence I needed to take up the space I was due. I was keenly aware of my limits and shortcomings. But by putting myself in the shoes of my boss, I gained clarity on my professional strengths. I realized how much he valued and needed me. How much I helped him. And what his professional life would be like without me in it.

This exercise gave me an accurate assessment of my real value, and changed the entire way I engaged with my boss, colleagues, and staff. It gave me the humility and empathy to be curious during times of stress. And it gave me the audacity and confidence to express bold opinions to leaders throughout the organization, without being pushy or pretentious. With this new attitude came new recognition. I earned the best reviews of my career. Started mentoring everyone I could, even if they didn’t know it.

In order to build employer value, you must learn to solve problems. But here’s the catch: these problems can’t just be little mental exercises you invent. They have to be actual problems. In other words you must continuously engage your leaders. Ask them about their professional goals, strategies, and tactics. Inquire about their pain points. And then listen. I mean really listen. Not just to the words they say, but to the words they don’t say. Watch the expression on their face and hear their tone of voice. Empathize with them, both verbally and attitudinally.

Whatever your industry or field, no matter your rank or role, everyone has a boss. And you will be well-served to proactively engage yours, and then continue to gingerly extract the information you need so you can effectively help them reach their goals and solve their problems. Then match these issues to your super powers, those skills of yours that are rare, if not inimitable. These skills are your differentiator, either from other job applicants, co-workers, etc. And when well-honed they become a competitive your advantage. If you do this, you will have a job as long as you want it.

As you look to accelerate your career, it is imperative you continuously improve the ways you tell your professional story. This goes beyond your resume. Of course your resume should be up to date. But most hiring managers just glance at those. Far more important is the ability for you to convincingly and passionately summarize your work experience in person, over the phone, and on video. You cannot practice this too much, especially since your professional story will always changing. Depending on your field, you might also require supplemental materials, such as a web portfolio or video reel.

Before you walk into a meeting, you should be able to confidently address these issues to any potential partner, employer, investor, etc.:

• What value did you build at your company?
• How do you qualify and quantify that value?
• How did your value help the company’s bottom line? (hint: you must thoroughly understand your company’s business model, and be able to succinctly articulate your role in it)
• Specifically why were you successful?

I would never hire anybody who cannot clearly explain their employer’s business model, regardless of the position or role. All workers contribute to the bottom line, and if they are not aware of the underlying mechanics of their company’s revenue generation, go to market strategy, customer base, etc. (at least at a high level), why would I assume they would ever learn it at a new company? Most companies do not make this information readily available, so you have to be prepared to chase it down. Approach it like a journalist, and extract the information from those you trust.

Look, it’s no secret that life isn’t fair. And those of us burdened with being part of some minority know this better than most. But at the end of the day we are each of us responsible for our attitude, work ethic, discipline, determination, and passion. Most of us will eventually receive a shot, provided we show up with an abundance of energy and enthusiasm. And if we complement that with thoughtful research, we will be positioned to plow through any perceived obstacles and seize each opportunity that arises. Such that we can experience fulfillment. Manifest purpose. And build the life of our dreams.