Five Obstacles You Didn’t Know Were There

Google phrases like “biggest obstacles” or “overcoming obstacles in life,” and what you’ll find is a lot of boilerplate that could have been written by the Advice-O-Matic 2000. You don’t need me to tell you that high levels of debt, toxic “friends” or a lack of mental endurance are major hurdles to personal growth. Still, you’ll find piece after piece advising you to remove only the most obvious obstacles in your life.

But what about obstacles we don’t even know are there? Ones that are so ingrained in our minds or woven into our day-to-day lives that we can’t even see them in the first place? Just as fish don’t know what water is, sometimes we can be so close to an obstacle — so wrapped up in it — that we’re not even aware that it’s holding us back. Obstacles like these are the water you swim in. They’re also the most dangerous.

In my years of teaching The Art of Charm’s bootcamps, I’ve noticed five common obstacles most men aren’t even aware are holding them back. I’ve also found that cutting out hidden obstacles can often have a greater impact than removing the most obvious ones. So let’s talk about overcoming obstacles in life that you probably weren’t even aware of, starting with…

Goals that don’t make sense anymore

As you know, we’re big on goals. SMART goals (put simply: objectively verifiable goals that you can reach and measure in a certain period of time) give you something to shoot for and something to track. They let you know you’re making progress.

Still, a goal isn’t useful because you complete it; it’s useful because it’s guiding you toward a meaningful result. That desired result often evolves as we work toward the goal, in which case the goal isn’t an end in of itself, but rather a guide on your journey. As the old saying goes, let’s not confuse the map with the territory.

So goals can change. In fact, they should change. Which means that at some point or another, if you’re doing it right, your goals won’t make sense anymore. At this point, you can either change your goals, or continue to pursue obsolete ones — a common hidden obstacle.

Let’s say you work in sales. You set the goal to book a certain amount of revenue because you’re angling for a big promotion. But it might make more sense to focus that energy on developing managerial skills so you can lead your division next year. Or maybe you’ve discovered that you don’t love this job anymore. Do you continue chasing down customers? Do you begin taking on managerial roles? Or do you continue to do your job while you hunt for a new one?

In this case, your true goal would be to develop a new set of goals, rather than to move up a ladder you don’t even want to be on. Confronting that fact, however, can be intimidating, difficult or straight-up impossible, since we’re so wrapped up in our jobs that we often can’t see them clearly.

The truth is, we all get so caught up in pursuing goals for their own sake that we often end up chasing things we don’t want. We don’t take the time to consider whether our goals are useful tools or abstract aspirations. Without the important step of evaluating whether a goal is meaningful, whether it even makes sense anymore, we end up chasing results we don’t want or wondering why it’s so hard to achieve our goals.

So periodically — probably every couple months or so — sit down and evaluate your goals. Measure how well you’re moving toward the goalposts, but push yourself further. Ask yourself whether those goalposts are even in the right place. Do your goals still make sense? Do you even want what these goals are promising? If not, how can you change them to better reflect what you’re really after? It might seem overwhelming, but regularly evaluating your goals is far easier than waking up one day and discovering you’ve been chasing the wrong things.

Productivity for its own sake

Getting things done is great, but some guys chase productivity for its own sake. When they’re not busy, they’re stressing over new ways to become busy. There’s no forward motion, just an endless cycle of tasks being completed. What’s most alarming, though, is that productivity can camouflage itself as success. After all, can getting so much done really be a problem?

In a word, yes. Productivity becomes a problem when it’s not truly getting you anywhere. You can end up stagnant, spinning your wheels, wondering why you’re always busy but never making real progress toward any end. Most commonly, productivity becomes an obstacle when it creates compelling reasons to avoid doing real work — when the short-term rush of getting things done replaces the long-term gratification of working toward the things you truly want.

This obstacle becomes even more obvious when you realize that some of the most rewarding experiences of your life will be the opposite of productive. Camping, for example. Camping is basically going out in the middle of nowhere to accomplish a whole lot of nothing. Or backpacking around Asia for a year instead of commuting to a high-paying job you hate. Which is ultimately more fulfilling? Which helps you grow more as a man? Which seems more productive?

Ultimately, of course, we still have to get things done. Along the way, though, give yourself permission to do things you enjoy, and don’t limit this to obviously “productive” activities like reading, woodworking or lifting weights. You need time for aimless passions and hobbies. They help us regenerate and recalibrate, and can often lead to new ideas, connections and inspiration (which are often super productive). You’re totally allowed to spend two hours going down a Wikihole about the history of pancakes, take a long hike on a day when you “should” be working, or wile away a Sunday afternoon binge watching Arrested Development, if these are contributing to your appreciation, sanity or happiness. If need be, block out time for “wasting time” on your calendar. Don’t feel like every waking second of your life has to “count” for something. Productivity and sloth alike are best enjoyed in moderation.

The wrong kinds of friends

Toxic friends are hard to ignore. More insidious, however, are the friends who just don’t help you move forward.

This friend is different from the guy who actively dismisses any attempt to better yourself. This guy simple doesn’t care about self-improvement — yours or his own. He’s not motivated to better himself. He’s not interested in cheering you on to greater success. He’s not driving you forward by pushing himself forward. He doesn’t give you anything to aspire toward. And because he’s not actively toxic, you don’t realize just how much he’s holding you back.

Which is not to say you have to cut him out of your life. Not everyone you know has to be obsessed with personal growth. But you do need people in your life who are driven in the same way you are. If you’re missing a highly-motivated circle of friends in your life, you’re missing the incredible support it can provide. You need the praise and encouragement that only motivated friends can provide. And you also need the extra drive that comes with a little friendly competition.

If you don’t have a circle of friends like this, get one. There are tons of ways to do it. You can join Toastmasters or a philanthropic group like the Elks. Just about every city has entrepreneurial societies, men’s groups, social clubs and sports teams for you to join and find other men as driven as yourself. Do a little digging, and you’ll find what works for you.

Jobs that aren’t giving you what you really want

People often find it hard to separate what society considers “success” from what they consider success. When you have everything you’re “supposed” to want, it becomes difficult to realize you have nothing you actually want. Because the truth is, you can have a high-powered, high-paid job in a respected field and be absolutely miserable. No matter how much money, respect and prospects for advancement you have, it won’t matter if your job isn’t giving you what you really yearn for. Without a job that is meaningful to you, you likely won’t feel fulfilled as a person.

So try this. Take a minute and write down what you love about your job, what you hate about your job and what you wish your job were like. A piece of paper won’t give you the right answer. But the exercise of thinking about what you’re getting out of work, what’s killing you and what you wish work were like can shed light on whether you’re even in the right place.

Next, think about why you go to work every morning. Sure, you need a roof over your head and three square meals a day. But I’d be willing to bet that once upon a time, you took the job because something else appealed to you about it. What is that “something else?” How can you get it back? Can you get it back? Ask yourself what you really want out of life. Beyond your basic necessities, how is your career helping you achieve your goals?

Switching careers and other drastic life changes aren’t always necessary (or even prudent). Just because you like the gym more than work doesn’t necessarily mean you should become a personal trainer. But systematically thinking about your career can help you recognize when a seemingly great job has actually become an obstacle.

A critical lack of self-awareness

Obstacles you didn’t know were there all stem from one place: Not seeing what’s right in front of you.

Inappropriate goals, the cult of productivity, unsupportive friends and unfulfilling jobs are just four common obstacles that are hard to spot. Every man has his own, and they’re holding him back in ways that often become apparent only after the obstacles are removed. Being able to see your hidden obstacles immediately, however, will help you become significantly more successful and far happier. That is a matter of self-awareness.

You can learn to recognize your own hidden obstacles — to become more self-aware — with a few different techniques. One of the most powerful is mindfulness meditation, which effectively trains your brain to notice events, patterns and sensations, as well as your mind itself. In addition to basic mindfulness meditation, you can also perform these exercises as part of your daily life:

  • Every time you walk through a door, ask yourself what got you to this point. Then ask yourself what your goal is as it pertains to walking through the door. What’s on the other side for you?
  • When you sit down to eat a meal, really pay attention to what you’re doing. Chew your food. Concentrate on the act of eating. Don’t see it as something to be gotten through. Be present.
  • The next time you do your dishes, don’t put on music. Shut off the television. Concentrate on the act of getting your dishes clean. Don’t rush through it. Make sure you do a good, thorough job at a regular pace.
  • Take any simple part of your daily routine, such as brushing your teeth, shaving or making your coffee. Try and execute every move as purposefully as you can with as little energy as possible. Note the difficulty involved in using as little energy as possible.

Finally, write down an objective summary of your daily events in a journal. Keep ruminations to a minimum. Every month or so, take a look back at what you’ve written. Do you notice any patterns? Does anything stick out to you as an obstacle that you hadn’t realized was there? Write a sort of “executive summary” of your life in regular intervals. Examining your most mundane activities in an effort to become more meditative, more self-aware, is a powerful tool for overcoming obstacles in life as they arise.

Which will help you navigate them with greater ease, understanding and confidence.

What are your hidden obstacles? How have you overcome these obstacles in life? Your experiences can be invaluable to helping other men slay the similar dragons, so let’s continue the conversation below!


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