Lessons In Loneliness: Look Beyond The Initial Feeling To Learn, Build, And Move Beyond

Leadership Lessons: As with “failure,” a freedom exists in the lessons of loneliness that can remind us to take care of and focus on ourselves first in order to move forward toward fulfillment, satisfaction, and happiness.

The theme and feeling of loneliness came up several times for me this week.

Luckily, it wasn’t my own.

Instead, it started when I published the blog post When It Comes To What You Want, What Does It Cost To Be Who You Really Are? In it I mentioned that the loneliness of an entrepreneur I had recently met was somewhat of the inspiration for writing the post.

A few days later, I read an article on NPR.org entitled Most Americans Are Lonely, And Our Workplace Culture May Not Be Helping, which cited a study showing that 3 out of 5 Americans are dealing with some form of loneliness.

Finally, to cap off the week…well, the third instance of loneliness was another of my own making, when I summed up some quick thoughts on those first two pieces in the short video below on Instagram.

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There are lessons everywhere.

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Now, before you read any further, please think about this topic differently than you normally might. I say that because (a) loneliness usually isn’t considered the happiest of topics, and (b) loneliness isn’t a topic that comes up too often when talking about development and self-care.

So, first, I say it’s not the happiest of topics because many of us have felt it at one point or another in our lives, so we know how emotionally draining and isolating it can feel. Understandably, those feelings give loneliness its negative connotation and can make us feel that if we share our loneliness with others, it will make us seem weak or less-than. Those feelings are also why our minds always seem to go to the worst-case scenarios and feelings when we hear the word loneliness. (For instance, what did you think when you read the first sentence I wrote here about the theme and feeling of loneliness? It most likely called up feelings of sympathy, despair, or maybe even pity.)

Second, when it comes to development and self-care, people tend to think about building up from where they are – their base – without really considering if that foundation is sturdy enough. A good amount of narrative in the personal development arena nowadays advises that it’s more important to build up our strengths than deal with our weaknesses. So, it encourages how we’ve programmed ourselves — to just keep pushing forward and set aside what may feel like uncomfortable feelings or off-putting weaknesses. That if we work hard and achieve enough in the positive direction, that alone will overtake, make up for, or offset the negative feelings.

So, because many may look at loneliness as one of those weaknesses, considering it a negative feeling, and, therefore, a negative experience in and of itself, they’d rather not talk about it.

And although I don’t want you to think of loneliness as a weakness, in the grand scheme of things, loneliness doesn’t traditionally come across as a feeling that allows you to push forward, grow, develop, or do your best. And that sounds more like a weakness than a strength. Hence, why our common view of loneliness understandable.

So, now, I want to try and begin to convince you otherwise.

You see, just like the idea of failure, where both loneliness and failure make us feel a sense of hitting rock-bottom, there can be good and growth in loneliness. (I use the word “failure” here to keep it simple, but here are some of my thoughts on “failure.” We need to reprogram ourselves away from thinking of failure as something devastating.)


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As an example of how loneliness can be good, I once got advice from someone (much wiser than me) who told me that Loneliness is freedom. Admittedly, it took me a while to understand what that meant. Yeah, on its face it seems to make sense: When you feel that loneliness, there is no connection, and so you’re not tied to anything. You’re free, right?

But there’s a difference between not wanting to be tied to anything and that being the case, and wanting to be tied – connected — to something/anything but not feeling it.

In the former, the disconnection kind of gives you what you want. In the latter, the disconnection is not at all what you desire and need.

And freedom is always seen as positive, while loneliness is generally viewed as negative, right? So, it sounds counter-intuitive to have one equated to the other. But let’s go through some steps to demonstrate there’s an advantageous freedom in loneliness.

A Restart

There is a silver lining to loneliness and “failure,” two very somewhat debilitating feelings. Like that previous quote “Loneliness is freedom” expresses, you’re free. You’re free from the pressure you feel (or imagine) from the groups around you. You’re free of the stress that’s dressed you down on your way to your current state. That stress was a perception and sensation of what might be, of what could go wrong. And, yeah, in this case it played out that way – you’re at what you believe is your bottom. But it’s done now. The slate is wiped clean. The canvas is bare.

What are you going to do with it?

Before, your landscape might have been packed with the expectations, desires, and needs of others that you might’ve felt you had to fulfill or live up to. Now, it’s just you. Now, maybe you might be able to breathe. The worst has happened, or the worst feeling has hit and is felt – and you’re still standing. (Have you ever realized that, generally, the anticipation of something happening tends to be stronger than when it actually plays out?) You’ve tasted what is likely the worst defeat you’ll face. Now what?

Now, you design and build what it is YOU want — and need.

A Reassessment

So, now you reassess. Before, you might have functioned or operated within the standards and priorities of others, standards and priorities you couldn’t relate to or fully connect with.

Now, you’ve had that restart of sorts. Now, you can rebuild.

So, what do you need? Who do you need? Which environments do you need to seek out after you’ve felt that loneliness? What are the factors you need to try to put into play to come back and work up from your downfall (or at least what you feel is/was your downfall)? What are your priorities?

Only you can know that. It ranges so much from person to person that the specifics can’t be covered here.

But now you’re free to decide what it is you want to build around you.

Related: Track And Assess Your Developmental Stages, Or Lose Out On Who You Can Be

A Reminder

Even though this loneliness might be yours, your road back doesn’t entirely need to be a solo exercise. And, no, that’s not a cute play on the fact that this post is about loneliness. It’s to say that if you do in fact feel loneliness, you yourself, for yourself and what works for you, most likely do need partners. And it’s not partners who serve as mere bodies for company to fill some void brought on by loneliness, although they may help. It’s to have partners to help, support, and, most valuable of all, challenge you!

Remember: You still need people. The right people. And they’re out there. It’s a matter of finding them. That’s the problem. People – all of us – may spend so much time sticking to the safety of what and who we know that we get locked into that group’s existence and dynamic. If we’re not jibing with that group, or feel disconnection in any way, we feel lost.

And there are too many people out there to meet, get to know, and learn from to settle for what might not make us happy. Like I said in the video, life is a game of numbers, trial-and-error. In this case, it’s about trying new experiences and people until we feel that connection or feeling of satisfaction.

Another thing to consider is that you may end up coming back to the same group and feel different. Once you’ve begun rebuilding yourself — restarting, reassessing — you’re a different person. You see differently. You look different because you think differently. You carry yourself differently. You and the world around you have a different kind of relationship between you. You are different. You may end up finding new value and satisfaction in both who you are and your current group.

Related: #SessionConfessions: What Makes You Feel Different Keeps You Aware And Sets You Apart!

Now, you are free to be curious and explore what you currently have.


All of this is easier said than done, I know.

The best thing to do is understand where you may fall when it comes to loneliness. Each of those questions and steps above leads to a different answer and a different path for each of us.

Keep in mind, also, that some people may be alone but not feel loneliness. Each of us is programmed differently based on our life experiences.

This is all general information above. It’s all a starting point.

Where do you stand? What do you need? What are you ready to do?

Make sure you take stock of everything you are and can do before giving into the feeling of loneliness.


Check Out These Articles

Like I said above, this post is just one way of looking at working through loneliness. Its message is one of self-assessment and self-reflection, so the work we can each do can take a good amount of time. But there are different approaches to loneliness and perceptions about what it means.

To hold you over while you work on yourself for the long-term, and in order to round out this conversation, take a look at a few articles below that offer short-term changes to make and steps to take in the meantime. Different pieces of advice and approaches may resonate differently with each of us, but they at least get us thinking.

(It just so happens these articles randomly popped up on my phone throughout the week — because, you know…technology.)

10 Little Things To Do When You’re Feeling Lonely

18 Ways To Stop Feeling Lonely



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