Gentlemen Speak: Why My Career Might Be the Reason I Didn’t Ask You Out

One man’s perspective on how professional stagnation can mess with a man and his romantic mojo
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One man’s perspective on how professional stagnation can mess with a man and his romantic mojo

I used to think that a man’s career didn’t have much effect on his confidence with women. Five or ten years ago, I didn’t have an overly impressive or glamorous career—nor did I aspire to one—and it didn’t cause me to second-guess myself when it came to pursuing women.

You might call it irrational confidence. I just called it me.

This unshakable confidence, however, came crashing down recently and has made me question my earlier dismissal of the connection between a man’s romantic confidence and his career. In fact, I now believe that my youthful aplomb is very likely more the exception than the rule for men as a whole.

Whether this is news to women or not, I figure it's helpful to hear what exactly is going on inside the head of a man whose romantic confidence is negatively affected by his career progression (or lack thereof).

So without further ado, here’s one man’s perspective on how professional stagnation can mess with a man—even the most irrationally confident of men—and his romantic mojo.

A Tale of Too Many Jobs and No Direction

I was never interested in jumping on the corporate track and riding it to financial security for its own sake. I had a liberal arts degree and an interest in teaching (and coaching). And the way I saw it, I had the gifts and the opportunity to make a significant and particular impact in a number of lives and make a living at the same time. There would be plenty of time later to build up my 401(k).

After college I landed a job teaching and was lucky enough to work with a woman I could see myself marrying. I was perfectly happy with my current situation, things were getting pretty serious with my coworker girlfriend, and I still wasn’t that concerned about the money.

Little did I know all that was about to change.

In a blink of an eye I left my teaching job, ended my relationship, and began another teaching job, which, after a few years, ended abruptly as well. The next year I spent my time in and out of jobs and working multiple at a time as I grappled with my future and what kind of employment would actually make me happy.

I had a hard time feeling good about anything. That feeling was amplified in dating—there was something particularly difficult about meeting new people.

Think about it: What’s the first thing adults ask each other when making small talk? “So, what do you do?” During this time, I found myself vacillating between being forthright about my lack of employment and avoiding the subject altogether.

It’s not as if I completely lost my confidence with the ladies or otherwise. But I definitely struggled with feeling like I didn’t measure up. I couldn’t help but notice that dates would expect a man to make more money than them.

My roommate would ask me, "Why don’t you go after Shelly?" And I would respond by saying that I didn’t quite feel up to it. It’s not that I stopped dating, but I definitely decided that I wasn’t in a position to go after the women I really wanted to pursue. Worse still, even if I did muster up the courage, what then? I wasn’t prepared to start a life with someone. I was worried about providing for myself, much less a wife and kids.

I’m Not the Only One

I’ve found that I’m not the only man who has experienced similar trepidation about pursuing women I admire for fear of unmet expectations. Recently, I asked my buddy Jay why he hasn’t made a play for a woman who we both agree is a catch (and who’s already spurned me …). “I'll wait until I'm financially stable and possibly thriving,” he said. I asked him to elaborate. Is his less-than-ideal professional status enough to keep him from pursuing women? He replied, “Yeah, her. She would want/need that. She’s the type where her dad needs to know what I'm doing to support his daughter.”

Then there’s Lewis, who has also found his personal confidence affected since experiencing a frustrating professional transition: “Ever since living abroad I have not been able to secure the employment I desire without having to go to grad school first,” he says. “I feel a little ashamed to tell prospective dates because they might look down on my career choice as I look for better options.”

A Cambridge study found that British men’s mental health is more adversely affected by job insecurity than women, though we’d prefer not to admit it. “Despite several decades of more equal employment opportunities for men and women,” Dr. Brendan Burchell says, “men retain traditional beliefs that their masculinity is threatened if their employment is threatened.” It’s no wonder, then, that men have also reported a higher rate of decreased sexual desire as a result of job insecurity as compared to women.

"In part there is a macho issue about men being the breadwinner," Dr. Burchell said. "Men, unlike women, have few positive ways of defining themselves outside of the workplace between when they leave school and when they retire.”

One of those few ways, of course, is in romantic relationships. So it’s not much of a stretch to imagine that if a man’s confidence is lagging in one area, it will affect another, and my experience and those of my friends bears that out. “I feel if I can hang on her level, with what is considered a promising career given the area that I live in,” Lewis continues, “then I can feel more confident in asking her out.”

It Might Not Be Such a Bad Thing

Rest assured, I’ve regained most, if not all, of the irrational confidence of my youth. I will say, though, that for a solid year and a half, it was a rather disorienting thing to deal with professional uncertainty, and I’m still dealing with some of the residual side effects.

But that doesn’t necessarily mean that I wish men didn’t have to deal with such things. Yes, as Dr. Burchell says, men feel a need to prove their worth through their professional pursuits, and that’s going to lead to frustration if things aren’t going according to plan. But any man worth his snuff isn’t simply wallowing in professional self-pity. We actually want to prove our worth. So when a man deals with the fallout of professional frustration, that can actually stoke the fires within us to burn even hotter.

That’s good news for any woman who’s in a relationship with a man who’s experiencing professional frustration, if you ask me. Sure, his confidence might be hurting a bit. But that has more to do with the fact that he wants to be his best self for a woman. If she realizes that, pledges her loyalty to him come what may, and encourages him to persevere, take risks, and pursue his passions, that can go a long way to helping him realize his potential.

I’ve experienced it firsthand: There’s great power in loyalty, especially in romantic relationships. When a man knows a woman will be by his side no matter what, he will believe he can weather whatever storms may come.

Photo Credit: Andreas Moulis