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The Gay Male Executive: Coaching for Success

Financial advisor consulting


The Gay Male Executive: Coaching for Success

In my experience (31 years in 2023) as a gay men’s specialist psychotherapist, I’ve met and worked w hundreds of gay male executives, who are among the demographic of the population who can afford private practice psychotherapy from a seasoned, experienced, multi-credentialed, specialist provider. 

As my career in this progressed, I expanded the scope of services I offer to include further specialized areas such as sex therapy (AASECT Certified), and Executive Coaching.  In addition to focusing on gay male clients who needed help with mental health challenges such as clinical depression, anxiety, ADD, OCD, PTSD, trauma recovery, personality disorders, and addictions, and life challenges such as HIV/AIDS, grief/loss, social isolation, sexual dysfunction, and relationship conflict, there were all the issues related to work, often in what I call “high demand, high reward” jobs, where the job required a high level of education, skill set, and leadership abilities. 

Gay male executives can face significant discrimination, both overt and very subtle/insidious, but they can also have White Privilege, Male Privilege, and Class Privilege.  The gay male executives I work with as clients often report a balance of these factors that are largely out of their control; they are based on who they are, not what they do.  The What They Do part is their way of coping with these factors, where as motivational speaker (and former psychotherapist) Jack Canfield (author of the Chicken Soup for the Soul franchise as well as The Success Principles, one of my favorite books) calls it, “Event + Response = Outcome.”

Here, I’d like to share an amalgamation of some of my experiences providing Executive Coaching services specifically for adult gay male clients; what it is, and how it can be helpful in the over-arching, long-term career of gay men in the commercial workplace, which can include non-profit organizations, religious institutions, schools/colleges/universities, public sector roles, politics, the arts, and private industry corporations. 

There is a combination of factors that help spell success, or relative frustration, in the career of a gay man.  Let’s discuss these factors, and their relevance:

Family of Origin as Factor in Success

When we talk about the factors that either contribute to, or detract from, “success,” we need to consider the variations of what “success” means for people.  Some would define themselves as “successful” if they earn a lot of money in the modern economy.  Some would define it as “being happy” in what they do.  Others would define it as being of service to their fellow Humankind.  Others would define it as their ability to effect a change or goal of society, such as educating America’s youth, cleaning up the environment, moving toward a more just society, advancing human technology, achieving scientific discovery, creating a body of artistic/creative work, or working to fuel avocational activities that give life meaning and purpose outside the workplace. 

For gay men, we often discuss that we live with a Family of Origin that we grow up with, with the variables of family size, race, nationality, ethnicity, socio-economic status, level of education, health “ability” versus “disability”, social privilege (or lack thereof), and local geographic influence (rural, suburban, urban). 

Both therapists and coaches might conduct an assessment on a client that involves learning about their Family of Origin, and generally whether it was robust and supportive, or challenging or even demoralizing/traumatizing. 

Gay boys who receive relative tolerance, acceptance, support, or even affirmative celebration of their gender and sexual orientation will, in general, grow up with more self-confidence, less neurosis, and more feeling “equipped” to take on the world and their goals with confidence, determination, resilience, and endurance.  Gay boys who grow up with privilege, whether socio-economic or with exceptional education opportunities, and are free of local stress (growing up in a safe, stable, robust local community) and stable, loving family life also have an advantage from a very young age. 

Gay boys who do not receive support, and are victims of homophobia from parents, siblings, grandparents, family friends, neighbors, clergy, teachers, coaches, and school colleagues will have to somehow work for adult success despite the instilled challenges of shame, low self-esteem, post-traumatic symptoms, poorer mental and physical health, lack of self-agency, fear, pessimism, resentment, defensiveness, vulnerability, and the cumulative fatigue of (minority) stress.  Gay boys who are people of color, indigent, differently-abled, medically vulnerable, living with “birth defects”, chronic medical conditions, or political/social instability (countries or areas affecting by war, poverty, civic chaos, or natural disasters) will have an early disadvantage that must be overcome to achieve success, even modestly. 

While some disadvantaged gay boys grow up to achieve executive success despite their Family of Origin conditions (perhaps by cultivating a powerful resilience, or even a defiance of their background), there is a correlation between gay boys who grow up with various kinds of advantage/privilege and their later success in leadership and executive roles.  Robust, supportive backgrounds as early as possible can give that child, regardless of sexual orientation, tools such as self-confidence, a lack of shame, boldness, optimism, and confidence that can be applied in so many ways that help him achieve “success” as he defines it in many ways. 


They say “Luck is when Preparation meets Opportunity.”  This underscores the importance of each of those, and why Luck can’t exist without the other two factors in the equation.

Preparation can be through mentorship and training later on, but it starts with education.  Higher SES gay boys might be sent to a prestigious private school early on, with a high-quality faculty, staff, curriculum, extra-curricular activities, and facilities.  Kids study better when they are not literally starving, or cold, or hot, or exhausted, or homeless, or abused/injured, even given the same general level of intelligence or natural aptitudes. 

Middle Class or lower SES boys, where perhaps most of us come from, can still benefit from broad public education, even in less-ideal conditions, if they are engaged, reasonably diligent, somewhat obedient (avoiding distractions of disciplinary punishment that waste time), and cooperative with the process, combined with at least some volition to assert their own interests and creativity, especially if their curriculum allows for some elective choices. 

Education is progressive: we start with Pre-K in some communities, and then a K-12 education as standard in the United States.  It’s usually the 9-12 grades that pave the way for access to university, and university paves the way for entering the job market based on rather raw skills learned in school. 

If gay boys can get through K-12 in one piece, without being so traumatized by bullying that it’s all they can do to survive and graduate, they are poised to carve out a professional identity for themselves even early on, based on their aptitudes, interests, and values. 

The education is the preparation part; the job market they enter into, and their ability to find an entry-level job, is the opportunity.  When these combine well, that is one lucky graduate, but there are many “land mines” along that path.  Not having enough money for college, being burdened by student loan debt, any kind of medical or psychiatric disability, a hardship such as an illness or injury, graduating into a poor economic climate, or discrimination/favoritism that has nothing to do with their education, skills, and qualifications are all potential deterrents to early opportunity. 

Education is perhaps the first place where future Executives learn the elements of leadership, such as knowing a field and its unique vocabulary, learning the importance of inadequate, versus adequate, versus exceeding, versus exceptional performance in support of organizational or institutional goals.  Education success is often associated with discipline; you don’t run off to a leisure opportunity when you need to study for an exam.  You don’t over-indulge in substances that make you miss class the next morning/day.  You don’t lose control with any kind of “vice” such that you can’t academically function.  You learn how to humble yourself enough to learn from senior faculty, counselors, and mentors, on the way to developing the kind of self-confidence needed to perform, and to move from largely “listen and learn” positions to “speak and lead” positions.


Much lately has been discussed about the economic realities of how young students become junior professionals who become executive leadership.  In days of a more robust economy, in past decades, especially for the middle class, before recent political movements have stifled opportunity and exploded wealth inequality, young graduates could get full-time jobs with benefits enough to get their own urban apartments and relatively high standard of living elements (food, clothing, transportation, health care, entertainment).  Currently, the broad lack of economic opportunity (skyrocketing rents, crowded shared living spaces, burdensome student and commercial debt, more scarce local jobs in a global (outsourced) economy, and geographic shifts (from classic American cities to obscure locales with “cheaper commercial real estate”) challenges the opportunity to become executive leadership quickly.  Add in the social pressures and stigma/discrimination that gay men face, and the lack of opportunity can be compounded.

What is antidotal to this, that I’ve seen with gay male executives over and over, is a resilience that helps them focus on education, skills, and determination to “do the job,” regardless of their own background and regardless of the influence of a small-but-powerful anti-gay contingent might have.  Successful gay male executives trample over homophobia by appealing to upper management’s focus (some would say obsession) with profits, prestige, and influence of the organization, which gay male executive employees often can contribute to very effectively.  It’s also more fashionable now and socially “correct” to hide homophobia and “get on with it” in business, increasingly so, and this is likely to remain, unless political and social negative forces gain power politically and legally in the immediate years ahead. 

Marketplace Context

Success for the young gay executive can also be about being in the right place at the right time for economic growth, opportunity, and technological/commercial trends.  Today’s executives are often selling products and services that didn’t even exist a generation ago.  Part of success is the ability to “trend-spot” and deliberately place yourself in environments that are associated with demand, growth, and sustainable operations that are not fleeting fads or temporary experiments of the Zeitgeist, but hold economic, commercial, and social staying power. 

Gay men can be particularly good at this because, as a group, we tend to be trendy bunch. We tend to be a social bunch, and even fashionable.  We have friends not related to us past college probably in greater numbers than straight men, who often experience loneliness going from their Family of Origin local buddies, to school/athletic colleagues, to college/frat colleagues, to work colleagues and wives/children but with fewer socialization time with adult male peers.  Gay men spend a lot of time with adult (gay) male peers, single or partnered/married, when they are parents or not, and in many leisure settings (including international travel). 

Middle-aged gay male executives need to balance the idea that they are not “kids” anymore in the workplace, they have respectable experience, credentials, and skill sets, but have to balance this with undermining from younger colleagues out for their jobs who are ready to set the world on fire, while even higher upper management who would love to get the same work done for a cheaper price by hiring younger, less-expensive staff and being rid of middle-aged or senior staff who have built higher salary histories.  What they lose when they do this is the “institutional knowledge” that can only come from experience and knowing the history of “trial and error” strategies in that same company that have been tried in the past.  Part of the executive coaching that I do with middle-aged men is helping them to make adjustments so that their work remains interesting/challenging, and doesn’t get boring, to tide them over until they are truly in a place emotionally and financially to retire, which might be, for example, from their forties to their sixties. 

More senior executives might need coaching for when they are retiring, and need to clarify a sense of purpose for a “next adventure” in their senior, post-retirement years, which might include identifying and pursuing a whole new “retirement career” that aligns with their values, interests, and “bucket-list” items.  Part of this would be informed by how much money, if any, they need to work to earn after retirement from their primary field for financial supplements to their 401k or Social Security, or just to “keep busy” doing a job they just find fun, which can be consulting, teaching, some kind of low-pressure sales, a creative field like art or writing, or LGBT rights advocacy, which could be paid or volunteer.     

Competing in a Straight World

Executive Coaching can often involve how to recognize, define, address, and ultimately overcome classic challenges.  The challenges to success for gay men are somewhat different (or in addition to) those of straight men, or even straight women, lesbians, or trans people. 

Success is a balancing act between factors that can be an advantage (right or wrong (often wrong), as a result of the Patriarchy, sexism, or racism, such as Male Privilege or White Privilege), and factors that can be a disadvantage and hinder otherwise qualified professionals. 

These can include homophobia from men, homophobia from women, homophobia from clients/customers the organization serves, glass ceilings, and dealing with specific workplace stressors such as injustices, discrimination, favoritism, cronyism, or workplace bullying.

Homophobia from male senior management or peer colleagues, or even direct reports, is a common challenge I hear.  Straight men can have a contempt for gay men because they are religious and find us “immoral,” or they can have Toxic Masculinity that makes them feel they are going to be good-and-goddamned if they are going to report to, compete with, or “forced” to collaborate with a, well, “the other f-word.”  Straight direct reports can have an attitude that “gay men aren’t really men,” and therefore are not worthy of respect, or they aren’t worthy of respect to be in authoritative or management positions, which can lead to either low motivation, lack of cooperation, or even outright insubordination.  In today’s more progressive climate, this is, thankfully, more rare, but I hear examples of this.  Certain cultures or “types” of employee will resent reporting to a gay man, just as some sexist men will resent reporting to a woman manager, or some racist people will resent reporting to a person of color or immigrant. 

Homophobia from women can include the same disdainful “gay men aren’t really men” bigotry, or a resentment that they have to report to a gay man when they wouldn’t mind reporting to a straight man, because they are indulging in gender-role stereotypes and their own internalized sexism that “that’s as it should be.”  Homophobia from women can include a resentment that men are still in positions of authority, when enough women are not, and if any minority is going to be an executive, it should be them, not gay men or people of color.  This is, of course, from especially bigoted women, and there are plenty of them (women for Trump, etc.). 

Homophobia from clients/customers the organization serves requires fairly strong, upper management policy that that won’t be tolerated, even if it means losing business.  A customer who wants “a straight male salesperson versus a gay one” should be met with the same hard boundary as a customer who wants to wait to work with a White male staff versus a woman or a person of color.  Good management really needs to back up all minority staff on this, and send a firm message that won’t be tolerated, even if it means losing the sale or the client. 

While any employee can face an injustice such as being passed over for a promotion they are qualified for, or nepotism or cronyism from the hiring manager, for gay men, the likelihood of some kind of injustice is higher.  I experienced two significant episodes of workplace bullying in non-profit organizations from jealous female perpetrators, which created a crisis for me and significant discrimination, and after that, I worked with a number of gay male clients who experienced the same thing.  Workplace bullying is a form of Toxic Competition, and it can come from colleagues above, beside, or below you on the organizational chart.  The kind of experience I had was before there was more recognition of workplace bullying as a phenomenon, and it’s about any kind of abuse of power that is designed to compete with, intimidate, belittle, undermine, humiliate, challenge, frame, or thwart their targeted colleague. 

All of these are complex topics that clients of Executive Coaching can benefit from, first to just reduce isolation and helplessness, then to be able to “vent” the situation, and strategize with resources from the executive coach as specific advocate for your best interests.   This can include how to communicate with others, how to document wrongdoing, how to identify witnesses, how to assert limits and boundaries, how to defend from undermining or false accusations from competitive colleagues or disgruntled former employees, how to report/coordinate with HR, and how to identify and work with an employment attorney to negotiate “relief” or to negotiate a settlement that helps the company avoid (an expensive) lawsuit.  But when some kind of legal action or process happens, an executive coach supports you as their client through the process, which might involve role-playing a deposition or court testimony to feel calm, focused, and empowered.  (It has been rewarding to see many guys I’ve worked with on this ultimately receive lucrative financial settlements, to at least try to recoup some of the damages of being discriminated against or harassed in the workplace.)

Being an Employee

Executive Coaching when we are focusing on You the Employee can involve ideas and support to achieve work/life balance, manage the stress of leadership roles where “everyone wants a piece of you,” advocating for your total compensation of salary, benefits, bonuses, stock options, or time off (such as paternity leave), strategizing the growth of your titles and salaries over time in the arc of your career, coping with decisions regarding where to settle or whether to relocate for a new job opportunity, and balancing the Life demands of being an executive with being a partner/husband/father. 

Being an employee means that you are “sandwiched” between your direct reports and the person/people you report to, and while you need to develop skills to support your team, someone (like the role of the coach, off-site) needs to support you, beyond what your own boss can do, who is really only supporting you to function well in the workplace for the organization’s advantage, when you also need support for your personal reasons that have nothing to do with the organization you work for. 

Being a Boss

Executive Coaching can also support your role in being a boss, with duties in outreach/recruitment/networking, decisions in hiring, supervising others, leading a team, disciplining employees, and terminating employees (which is one of the least-favorite functions executives report having to do). 

Improving your skill-set in all of these, from goals you set for yourself, is a part of the either short-term or ongoing support from an executive coach.  Having a chance to discuss sensitive issues in confidence, including how you might feel conflicted in various situations such as how to hire the right person between two (or more) equally-qualified candidates, or how to legally and even compassionately (as much as you ever can) fire someone, can be an important opportunity.  Unlike “Employee Assistance Programs,” which, ultimately, have staff paid by the management, executive coaches have only a loyalty to you.  Even criminal wrongdoing is still held confidential; there are no “reporting” mandates for coaches with the exception of endangered children, disabled adults, the elderly, or direct threats of bodily harm to someone (although I will still discourage slashing someone’s tires). 

Executive Coaching can be a private space to discuss HR issues with someone who is not actually in HR at your organization.  In today’s risky climate of “zero tolerance” for sexism, racism, and anti-Semitism (although, frustratingly, perhaps not as strict about anti-LGBT issues), executives need support, including in cases of false accusation, misinterpreted remarks, or accidental incidents when HR “isn’t buying” your defense.  This can largely be the purview of your private employment attorney, but coping with the related anxiety, frustration, rage, helplessness, resentment, fear, humiliation, embarrassment, and disorientation of the sometimes traumatic nature of certain situations can be in part the purview of the executive coach, and also the purview of a therapist, and when the provider is credentialed for both, there might a little “mix” of these, but ethics demand that a coaching function and a therapy function be kept separate to avoid confusing “dual relationships” and legal/ethical practice issues of both disciplines. 

Current trends such as the “zero tolerance” policies in some organizations that seem to want to “make up for” past climates where discrimination and offensive behaviors were, indeed, rampant, or topics that are popularized in the media such as those coined like #MeToo or local/national politics, can permeate organizational boundaries into the workplace. 

Career Through the Lifespan

Executive coaching has its infancy when a high school guidance counselor talks to you about potential colleges or majors, or when professors and mentors in college guide you about graduate school options or entry into the workplace.  Coaching takes into consideration that your professional development, just like your personal development, is something that happens throughout the lifespan, from your childhood aptitudes and talents, especially those that “stand out” among your peers, to your young adult high school and college years, and through middle age and becoming a senior citizen.  The years pass. 

Coaching that helps you meet the challenges associated with every phase of life, and to capture the traditional joys of each phase of life, can be useful.  Regardless of your field, careers in general tend to follow similar arcs of a beginning, middle, and end, with lots of zig-zagging highs and lows in the meantime. 

Coaching can involve how to navigate specific challenges, such as how to manage a career along with parenthood, how to manage a career and still have a robust “bon vivant” gay personal life that might involve elaborate travel or an active peer social group life, how to navigate a Midlife career change, how to plan for retirement in a personal fulfillment way (your Certified Financial Planner should be helping you in a financial way), how to create your “swan song” as the apex of your career, and how to cope with retirement and the potentially sudden loss of professional purpose that can bring, which can be a risk for depression, which is when a therapist comes back into the picture. 

Philanthropy and Community Involvement

Lately, I’ve been working with more clients on how, if they have the means, clients can identify their interest in philanthropy and community involvement.  Often, as we age and build our salary history and our incomes, we think more about “giving back” through philanthropy, especially for gay men who might have “surplus” resources of money or time because we usually are not raising kids and paying for college or weddings. 

Philanthropy (as I’ve learned from my husband, who works in this field) can be about clarifying your values, and your interests in what you want to support financially as an expression of those values.   Common topics include, of course, LGBT+ rights, LGBT youth, animals, the environment, the arts, education, and politics.  You can make direct donations each years to 501-c-3 non-profit organizations for a tax deduction, or more elaborate things like funding the principal for an annual scholarship in perpetuity, or leaving a charitable bequest in your will, or providing funding for a specific project or building that brings “naming opportunities” for you to have something named for yourself, or in honor of someone else. 

Coaching can help you clarify your values, and help you identify what kind of legacy you want your professional and personal impact to be, for the times long after you’re gone from this lifetime. 

Legacy/Making your Mark

Other recent clients have been discussing the role of legacy in a career, where it’s not “just” the body of work you do in the course of probably many years in your career, but it’s what kind of “mark” you want to leave in your field, which might inspire others in the same field later.  In Hollywood, where I live in Los Angeles/West Hollywood, we see the “legacy” of the film work of the great directors like Robert Wise, Billy Wilder, Frank Capra, or George Cukor (gay man), or the great costume designers like Edith Head or Charles LeMaire (another gay man).  These very visible figures in the very visible entertainment industry might be the easiest examples to find, but every field tends to have its “legacy pioneers” who made the field have impact initially, or took the field to the next level through innovation.  Not every executive has this happen, but it can be rewarding to think about what kind of impact or legacy you want to leave in the field in which you work.

The sometimes stark reality is that a career goes by fast – faster than we realize.  After doing this work (therapy and coaching) for over 30 years, I’m probably closer to the end than I am to the beginning, especially if I ever want to retire and shift my own professional and personal identity (to be determined).  It’s important to try to “do what you want” as much as you can, “before the parade passes by,” to quote the show tune from (gay) Broadway composer Jerry Herman (“Hello, Dolly!”). 

Executive Emeritus

Executive Coaching later in a career, just before retirement or often just after, can be about embracing a role I call “Executive Emeritus,” much like the term “professor emeritus” an academic might have later in life.  You have the luxury of really picking and choosing if, and how much, you want to “work,” perhaps as a consultant, mentor, or confidant to professionals who are still working in the thick of it. 


Not everyone needs or wants executive coaching, but the relief of having a “credentialed confidant” can make a guy feel safe, supported, empowered, “professionally potent,” competitive, capable, and productive.  Asking for help doesn’t mean that symbolizes failure or inadequacy, like “validating Imposter Syndrome,” but instead is the opportunity for self-empowerment and the commitment to your best professional self being actualized for this job, and for this lifetime.

If you are interested in any of my professional services – therapy, couples therapy, sex therapy, or life/career/relationship/executive coaching, you can learn more by calling or texting 310-339-5778, or emailing or  I’d be happy to help!

Ken Howard, LCSW, CST has been a gay men’s specialist therapist and coach in Los Angeles/West Hollywood for over 30 years.  He is a graduate of UCLA and USC, and had a long career in non-profit organizations as clinician and in management before launching his private practice.  He lives in West Hollywood, California, with his husband of 21 years, and can be found online in his home office, walking his dog, riding his motorcycle, writing something creative from self-help books to webinars to novels to musicals (“On the Boulevard,” available on all streaming services), to superhero fan-fiction.  Busy is good. 

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