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Five Work Transitions for Gay Men that Could Benefit from Career Coaching

Businessman showing thumbs upWhile I do mainstream psychotherapy sessions in my office for people with depression, anxiety, trauma, relationship conflicts, and many psychological disorders, I’ve also had many requests for career coaching in the past year especially.  Many guys have friends, bosses, family, and maybe even a mentor of sorts, but career coaching fulfills something none of these other roles do.  Having someone to “vent” to, who can give you feedback about your career track, skills-building, networking, salary increase plan, satisfaction, and even long-term retirement planning, can really help.  Unlike psychologists, clinical social workers like me help people more specifically with all aspects of your life, in the “person-in-environment” theory, part of what I teach as an Adjunct Assistant Professor at USC School of Social Work.  Often, you need practical support for your career, to put yourself at your best advantage.  For gay men, navigating a career has some special and important considerations, both positive and negative, which involve everything from homophobia/discrimination in the workplace, to a “lavender mafia” where networking among your fellow gay men is actually an advantage. 

I’ve found that there are generally five transitions in work that really benefit from career coaching, as I see these situations with clients often in my office.  These are:

1.  School to Work – Finding work for Millenials after college has been tricky after the Recession, but it’s getting better fast.  For guys making the transition from school to work, coaching can help you learn the differences between the school environment of performance, competition, socialization, and work/life balance and the “working stiff” routine.  When I work with younger guys, as a middle-aged man myself, I try to give guidance that I wish someone had given me at their age.  It’s a “realistic optimism” of how things work: not too naïve, but not too cynical, either.  I recommend various books and informational material, and how to incorporate those, so that you set off on the right foot.  Things like retirement savings, investment, planning a course for skill-building, and planning for the standard of living you want (such as renting an apartment vs. buying a home or condo; what kind of car/clothes you want; what type of work/life balance you want; and what kind of compromises (which are a must) that you’re willing to make.  This transition is critical, because school to work is a real turning point in your life as an adult, and decisions you make now have implications for many years to come.  Do it right. 

2.  Staff to Management – There are many guys I’ve helped who have been doing a good job as a line staff, and then that pays off into being promoted into management.  The first time you have either management fiscal (financial) responsibility, or you have staff reporting to you, is critical.  This is how you earn more money, get more prestige on your resume, and really “play with the big boys” (and girls!) in business, in any field.  Almost no one makes the “big bucks” in work without having either financial or staff responsibility.  My management coaching and executive coaching help you balance your life with increased work demands, how to handle bigger decisions, how to coordinate staff, how to resolve conflicts, and how to fairly hire, evaluate, or even fire staff.  It’s rare that your bosses would do this, because they’re busy, but you often need someone to “bounce off of” because you can’t do it confidentially that easily with subordinates (certainly), colleagues, or superiors.  Having off-site coaching for management issues helps you to be a better manager – and a less stressed-out one!

3.  Staff/Management to Freelance – In Los Angeles, with so few Fortune 500 companies, the economy is driven by many freelancers. Entertainment, law, real estate, retail stores, restaurants, personal training, interior design, contracting, home repairs, and fashion are filled with what I call the “gay solo entrepreneur”.  The transition in going from working for someone else to working freelance is a big jump, but an important one.  You have tons more autonomy, but also more responsibility and the stakes are higher.  You can earn more, but you also have to, in order to cover your overhead and taxes.  There are no “paid holidays” as such, but you can take a day off whenever you really want to.  Dealing with marketing to our ideal client, assessing the competition, defining your niche market, balancing the personal with the professional, and attending to both the creative and the commercial, are all themes what I work with in coaching my clients.  The transition from “workin’ for the man” to working for yourself is daunting, but of course it’s exciting, too.  Most freelancers benefit from coaching because it gives you someone who can cheer you on emotionally, and yet guide you practically, in a way that you don’t get from anyone else, because it’s in a clinical (as a therapist) context, plus there is the consulting benefit of my having worked with so many solo entrepreneurs (and seen how they solved similar problems) over my 23 years doing this.  This is both coaching and consulting, really. 

4.  Work Relocation – One of the more unusual, and yet still frequent, requests I get is from guys who need help trying to decide whether to re-locate from living in or near Los Angeles.  Relocation is a psychologically stressful event, and it is considered in research to be one of the more challenging events a person can do. Think about it; your workplace setting, your home, your friends, your economic/geographic/climate environment all change at once when you move.  And yet moving to another city often means “moving on up” in your career. Helping you weight the pros and cons of such a decision in coaching can be a big help.  Also, helping you process what you might lose (familiarity, friends, seniority) and what you might gain (salary, new opportunities, better cost-of-living city) can be helpful.  When you’re faced with such a dilemma, having support can help you make the right decision, for you, for this time. 

5.  Work to Retirement – There are many times when I work with gay men who are fortunate enough that they have earned enough money by a relatively young age that they are reasonably financially secure for life.  They can afford to retire early, usually from a variety of circumstances: their business made a lot of money, they sold their business, they inherited from their family; a start-up took off in an IPO; or they earned a pension from a young age (police officer, military, public sector, firefighter, etc.).  But this is not all good news.  Gay men who retire “early” can face boredeom, restlessness, isolation, loss of purpose, self-doubt, and even existential crisis.  Coaching at this time helps to restore identity, increase new/different socialization, find new meaning in life, establish a new/better role in the community, improve physical/mental health, identify meaningful philanthropy, and plan the next “phase” of life with plenty of life expectancy left, even after a traditional work life is over. 

Of course, there are other transitions and challenges that could benefit from coaching, such as overwork.  Are you facing any of these transitions?  If so, give the idea of receiving coaching some thought.  Think about the transitions you would like help with.  Some discount sessions are available Monday through Friday afternoons, and I have evening times, too.  I work in my office, and also via phone or Skype if you can’t get in the office locally (near Beverly Center) or if you live outside of LA.  I coach clients in Berlin, Washington DC, New York, San Francisco, Chicago, Phoenix, etc., so we just schedule around the time zone differences.  Payment is easy via PayPal or credit card on Square.  If you need weekend assistance, two clinical associates are available then.  For more information, call my cell at 310-339-5778, or email  Straight women, lesbians, and straight men are also welcome.  Get the support you need to have the career you want!


Ken Howard, LCSW, is a gay and HIV-positive (25 years) licensed psychotherapist (LCSW) and life/career coach who has specialized in working with gay men, as individuals and couples, for over 23 years.  He helps many gay men (and others) resolve the issues that undermine your quality of life, and helps you to thrive.   

For help improving your personal or professional life, whatever your current challenges are, consider sessions with Ken for counseling, coaching, or therapy sessions, at his office in Los Angeles/West Holllywood (near Beverly Center mall), or via phone, or via webcam, anywhere in the world.  Call 310-726-4357 or email for more information.

Ken is also available for expert witness work on legal proceedings involving gay issues, all LGBT issues, HIV issues, and issues concerning psychiatric illness or disability, as well as organizational consulting for non-profit organizations, corporations, college campuses, and conferences. 

To get your copy of his self-help book, Self-Empowerment: Have the Life You Want!,visit , or  It's your "portable therapist" for the challenges you face today in your mental health, health, career, finances, family, spirituality, and community.



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