10 Signs You Know It’s Time to Throw in the Towel on Your Career

his is a story about failing to achieve one’s career goals and knowing when it’s time to finally give up and move on to greener pastures. It’s a story about being completely oblivious to the warning signs that you may be on the wrong track and at risk of living a life of frustration, unhappiness, and futility. There’s a good chance you’ve thought about quitting something you’re passionate about at least once in your life, but for one reason or another, you stuck with it. But I’d wager there are plenty of people who may be struggling with the indecision so hopefully, my story may offer some relief with a new point of view.

I am, or should I say, was, a professional freelancer of twenty years (not a writer in case you are wondering) who has finally accepted that my career has all come to this: an unspectacular finale. A career I once idealized for so long has finally faded out of reach forever. I’ve learned, however, that acceptance can be cathartic. But this is not a story about acceptance. The pandemic has provided me an opportunity to distance myself and look at things more deeply. Time has allowed me to go above myself — to a place of higher-thinking beyond my clouded emotions and to see objective truths, or more precisely, to discover an accurate understanding of my reality and fortunately turn a personal tragedy into a triumph.

There is not a whole lot written on the subject of quitting because it’s a painful subject to talk about, let alone follow through with. No one likes to face the proposition of giving up since it’s a major buzz-kill on our ego. Who can stomach the idea of labeling themselves a quitter and dealing with the embarrassment of not measuring up, not being good enough, strong enough, or resilient enough to persevere? Edith Weisskopf-Joelson put it perfectly when she said, “we are given very little opportunity to be proud of our suffering and to consider it ennobling rather than degrading.” — When you reach the point of not being ashamed to be unhappy anymore you can find the strength to surrender.

But we don’t like to hear stories from those who make the decision to tap out. I guess those tales wouldn’t be too inspiring. We prefer to hear from the winners and their narratives of success and happiness because our society is characteristically achievement-oriented. It’s easy for them to preach to us their positivity, tell us things like, never quit, follow your dreams, persevere, hang in there to the bitter end, dust yourself off, get back up, try, try, try again until successful, etc., etc., etcWe are engrained with these societal idioms to the point we feel guilty when we have any thoughts of self-doubt or any thoughts of maybe this isn’t right for me. So we don’t stop. We keep going, and often, unbeknownst to ourselves, it does us more harm than good.

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Silviu Zidaru Unsplash

After two decades, I’ve finally been able to let my dream go — like setting down a leaf in a stream and stepping back to watch it peacefully drift away. The frustration, resentment, bitterness, and envy (thank goodness) floated away too. I finally understood how unhappy I was for a good chunk of my life and I figured out it was because things weren’t going the way I wanted them to go.

The world is, as it is, not as I wish it to be.

Years later, I finally had the epiphany I needed and realized I was an entitled idealist, a daydreamer, desperately trying to bend the world to my wishes. I was hung up by an unrealistic attitude of how things should be and failing to learn how things actually are. I never understood that we ultimately operate within the boundaries of our endowments and environment. Instead, I fantasized about things I could never attain. Today, my favorite mantra I adopted better late than never is, The world is as it is, not as I wish it to be. This mantra continues to be my guiding light, keeping me calm and tranquil when dealing with my most difficult challenges.

You have to think about every choice, like a bet which comes with a probability of being right and a probability of being wrong.

One of the key things I discovered is you have to know how to make wise choices in life. It sounds banal to tell someone this but how someone goes about making the right choice is what matters. You start by simply looking at any given situation and properly weigh the pros and the cons. You have to think about every choice, like a bet which comes with a probability of being right and a probability of being wrong. Our lives are, in effect, an accumulation of incremental little choices. Most people believe that anything is possible, but it’s the probability of ‘anything is possible’ occurring that matters most! People who can discern the possibilities from the probabilities tend to be more grounded, practical thinkers who can manage their emotions and their reality better than the idealists who get stuck day-dreaming.

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“Iceberg, Right Ahead!” — Titanic, 20th Century Studios

Your task is to combat the emotional and irrational assumption that you will eventually succeed if you just keep at it and hang in there long enough. Frankly, this is terrible advice because life doesn't guarantee anybody anything. You need to look for the signs that spell trouble ahead and utilize your own logic and reason to help you realistically determine your probabilities of success. Below, are ten signs it could be time to pivot and move in a new direction. You don’t have to stay the course if you see danger ahead. Remember the Titanic — staying the course can be disastrous.

1. You keep telling yourself things will eventually get better.

Consider at what pace are you improving? It’s not acceptable to be satisfied by making any kind of progress. Telling yourself and other people, “things are going okay.” when you’ve been working five to ten years with little to show for it can be a huge trap! It’s the level of improvement in relation to the rate of change that matters. Everything important in your life should be on a trajectory towards excellence at an appropriate pace.

2. You are trying too hard.

If everything feels like a battle to make any measurable progress you might be trying too hard. Wu Wei translates to not forcing. As Carl Jung said, man needs difficulties, challenges, and obstacles that are there to strengthen you, push you to your limits, and maximize your potential. But if your struggles feel forced or resistant, your likely rowing against the current instead of sailing with the wind.

3. You are an impractical idealist.

Like all people, you are under the control of your emotions and operating under confirmation biases. This means you subconsciously look for things that support your beliefs whether they are correct or not. You need to master your lower self and become a hyperrealist and not get lost in the clouds of idealism. Your reality is defined as the people you interact with most and the places you frequently visit. Work with what you have, not with what you think you’ll get. Become a grounded practitioner. Understand, accept, face, and deal with your reality.

4. Your networking efforts continue to have minimal effect.

My networking efforts never improved over the years. I would cold call, warm call, hot call, email, newsletter, coffee meet, you name it — I did it with marginal results. Of course, I blamed others for my lack of success, but the truth was I essentially had nothing new, better, or different to offer the market than my competitors. Stop believing you are a unique snowflake; the truth is everyone is replaceable and there are probably over a thousand others lining up who want your position.

5. The barrier to entry of your chosen profession is low.

Can any Tom, Dick, or Harry can get into your profession with little education, skill, or capital? Low barriers to entry create supply and demand imbalances making it near impossible to compete. Unless you are in the top 1% where people hire you on want (talent) you will find yourself in a race to the bottom. See ‘working in the middle market.’

6. Environmental circumstances are not in your control.

Sometimes there are major influences from things that are simply beyond your control. Find ways to minimize the control others have over you. Understand that while the worst circumstances can be improved with a different approach, know that your efforts are largely subject to circumstance and environment. On some levels, you are the plaything of fate.

7. You don’t fit in with the current ‘Tribe mentality.’

Birds of the same feather flock together. People of similar character, backgrounds, and tastes tend to congregate or associate with one another — and ultimately hire one another. You need to fit in, or you‘ll find yourself on the outside. For better or for worse, your life is affected by the people around you and how you interact with them on a daily basis, and your ability to get what you want is fundamentally dependent on working with others who want the same things as you. If you don’t share the same desires, principles, and values, you will never be ‘accepted’ into the tribe. You need to be crystal clear in what you want, seek out like-minded people, and then synthesize with them.

8. You work the ‘middle market’ instead of the top or the bottom.

Here’s the truth — The late Stefan Aarnio once said, “There is loyalty at the top as long as your the best, and there is loyalty at the bottom as long as you‘re the cheapest (race for the bottom), but there is zero loyalty in the middle.” The problem with the middle market, known as ‘no man’s land,’ is clients there are fickle and can afford to be choosey. The top of the market operates on a desire for the best while the bottom of the market operates on the need for the cheapest. You need to be positioned so your customers either need or want you. If you work in the middle market, they neither need nor want you.

9. No clear path to becoming extraordinary.

The hardest thing to accept is your best isn’t good enough. We have a natural tendency to overestimate our skills and abilities and our self-opinion is always elevated compared to reality. The consolation is you’re never as bad as you think. The world only rewards the extraordinary, and it’s the extraordinary people who will take market share from you. If there is no clear path to extraordinary in what you do, it could be time to re-think what it is you’re doing.

10. You don’t have a strong enough ‘why.’

I may have saved the best for last. After two decades, I finally accepted I wasn’t in love with my craft, but rather in love with the money and the lifestyle my career provided me. The perks were incredible, and the money was excellent, and as a result, the career was hideously and ruthlessly competitive. The truth is those who succeed at anything never set out for the money as their prime motivation. They do what they do because they are genuinely passionate about it regardless if they are getting paid because that’s who they are, by their nature. They have a strong ‘why’. Money always follows excellence, but it never works the other way around. Explore and find out who you are, and why you are, and then go do that thing that meshes with your natural inclinations.

Existence alone was never enough for him; he always wanted more. Perhaps it was only from the force of his desires that he had regarded himself as a man to whom more was permitted than to others. — Fyodor Dostoyevsky, Crime and Punishment.

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