Why You Feel Behind In Life (And How To Fix)

Do you ever feel like life is passing you by?

Your old school mate is raking in six figures while you're still figuring out your career.

Your friends are settling down, getting married—while your still searching for the right person.

Someone just bought their first house. You're still renting.

No matter how hard you push, you never seem to catch up.

Why does it feel like everyone else has life figured out—except you?

You're not alone.

Feeling behind in life is more common thank you think.

I've wrestled with these same doubts, and I've discovered three hidden traps that keep us stuck in this cycle.

Avoid them, and everything changes.

Trap 1: following the set route

“Do not follow where the path may lead, go instead where there is no path and make a trail.”

—Ralph Waldo Emerson

Most of us unthinkingly follow a set route.

Go to school, go to university, get a job, get married, have kids, climb the career ladder, retire.

That's the conventional wisdom and formula for success.

The safe, respectable path recommended by our parents or teachers.

Many of us take that route because we don't know any better. But it's a one-size-fits all path. Of course, it doesn't suit everyone.

Before long, we develop a niggling sense we've stumbled into a life that was never meant us.

On top of that, media and popular culture teach us to want something else.

Through movies, social media, news and advertising, we learn what's truly desirable is to be rich and famous—a member of the elite.

By definition, only a select few can be part of the elite.

So we struggle through life with this mismatch between what society seems to value and the path we are on.

We feel forever behind in life.

The first trap is following the set route without questioning it, and in the process tying our self-worth to society’s definition of success.

Instead, we should define success for ourselves—on our own terms.

Escape trap 1 - walk your own path

To escape this trap, you must think for yourself and forge your own path.

It doesn’t matter where you begin—just start today, one step at a time.

1. Accept where you are

Wishing things were different won't change them.

Yes, life might feel unfair, but dwelling on it keeps you stuck.

Accept where you are fully—it's the first step towards meaningful change.

2. Define your ideal day

Grab a pen and paper. Write out your ideal day.

Make it realistic—within the bounds of current obligations (work, parenting etc.)

• What would a good day look life?

• What is one small thing you could do for yourself—read, walk, work on that side project?

3. Define your ideal week

Now zoom out. Write out the your ideal week.

• What small actions would make your week more fulfilling?

• If you want to change your circumstances, schedule one step forward—30 minutes job searching, learning a new skill, or networking.

Remember, be realistic—choose actions you can actually follow through on.

4. Take one tiny action right now.

Look at your plan. Pick one thing and do it immediately. Not tomorrow, not later, right now.

In fact, do it before finishing this letter. I'll wait.

…

Welcome back. If you truly followed through, you've just taken control of your future.

The key now? Momentum.

• Keep your actions small and doable.

• Prove to yourself you can follow through.

• Build confidence in your ability to create change.

Before long you will truly feel you are forging your own path.

That's a huge step.

But if you don't escape the next two traps, comparison and self-doubt will pull you right back.

Trap 2 - playing status games.

A finite game is played for the purpose of winning, an infinite game for the purpose of continuing the play.

—James Carse

In "Finite and Infinite Games", James Carse explains that life can be played in two ways:

• Finite games - where you play to win. The games have fixed rules, a clear end, and winner and losers.

• Infinite games - where the goal is to keep playing. Games focus on growth, learning, and enjoyment rather than competition.

Most of us treat life as a finite game—a race to the top.

We chase titles, status symbols, and promotions, thinking they will make us feel fulfilled.

But it's a zero sum game—if someone rises, someone else must fall. And no matter how high we climb, it never feels like enough.

We are all playing status games.

Finite games are status games.

There is only one winner—the person at the top. Everyone else falls behind.

To rise, you must push others down. To stay ahead, you must constantly prove your worth.

Status games show up in all areas of life.

• School - children are ranked by grades in class and by popularity in the playground.

• Career - people climb the corporate ladder, chasing titles and promotions. The CEO wins; the rest compete.

• Social life - we measure ourselves against others, tracking who has "made it" and who is falling behind.

Yet, status games are inherently unsatisfying, for four reasons:

1. You obsessively compare

In status games, your rank isn't up to you—it's decided by others.

Your rank can change in an instant. A promotion, a new trend, a shift in perception—suddenly, you rising or falling.

So you obsess over what others think, constantly watching for signals of approval or rejection.

2. You chase status symbols

You want to be on top.

So you collect titles, wear designer clothes, buy the big house—anything that signals success.

You stretch yourself thin for that promotion, you spend on things you can't afford, you exhaust yourself proving your worth.

But the goal posts always move. No matter what you achieve, there is always a higher rank, someone better off than you, another rung to climb.

3. You live in the past

You're stuck in the past.

Status isn't about who you are—it's about who you were.

Your promotion? That was last year. Your big house? A trophy from games you played years ago.

Instead of focusing on what excites you now, you cling to past wins, afraid of losing your place in the ranking.

4. You rush through life

You race through life—only to find there is no finish line.

When life is a competition, you rush from one achievement to the next, always feeling behind.

Promotions, wealth, recognition—you chase them all, convinced they'll make you feel that you've arrived.

Only to find there was nothing to win, just time you lost.

Escape trap 2 - play a different game

Status games are unavoidable.

You have to go to school, you need to work, and whether you like it or not, people will judge you.

So how do you escape?

It's simple—stop taking the games so seriously.

Think back to when you last played Monopoly. There's always that one person who takes it too seriously—arguing over rules, fuming when they lose, forgetting the whole point was to have fun.

Don't be that person in life.

Instead, hold things more lightly. Treat life as an infinite game where the goal isn't to win but to learn, grow, and enjoy.

Here's 4 suggestions to help:

1. Connect, don't compete.

Status games force people into roles—boss, manager, "popular one". But beneath every title is a human being.

Stop keeping score.

Instead of competing, focus on connecting.

Build relationships based on shared experiences, not ranking.

Life becomes richer when it's about collaboration, not comparison.

2. Acquire skills and resilience. Not things.

The game is long and unpredictable. The designer clothes won't help you adapt, but curiosity and resilience will.

Follow your interests.

Learn skills that excite you.

Accept that some days will be hard, and train yourself to handle them with grace.

3. Look forward, don't look back.

The past is done—you can't change it. But your future? That's yours to shape.

If you define yourself by your past, you shrink your possibilities. You create invisible walls around what you can and can't do.

Instead, look forward. Every day is a chance to take your life in a new direction.

4. Run your own race.

Life isn't fair. Some people start ahead, others behind.

So why compare? How can you be "behind" someone who:

• Started in a different place; and

• Is going in a different direction?

The moment you stop measuring yourself against others, you free yourself to build a life on your own terms.

Forget the rankings—focus on creating your own path.

Trap 3 - an overactive inner critic

“Talk to yourself like you would to someone you love.”

―Brené Brown

The third trap is the hardest to escape.

Walking your own path and stepping outside status games—these are shifts you can make quickly

But an overactive inner critic runs much deeper—it's harder to detect and even harder to silence.

The voice inside your head

We all have a voice inside our head.

It narrates our experience, replays past mistakes, and runs through future scenarios.

It's a useful evolutionary trait that helps you:

• Solve problems.

• Learn from the past.

• Plan ahead.

Unfortunately, left unchecked, your internal dialogue can develop into something resembling a relentless drill sergeant who:

• Barks orders.

• Tears you down.

• Holds you to an impossible standard.

Sounds familiar? That voice isn't who you are, it's an overactive inner critic.

And if you let it take over, you'll always feel like your falling behind.

Escape trap 3 - be your own best friend.

An overactive inner critic develops over years—shaped by experiences, expectations, and conditioning. It takes time to unpick.

Many people (myself included) find working with a professional helpful to do the unpicking.

But there are simple strategies you can start today which help quiet the voice inside your head.

1. Recognise your inner critic exists.

If you've lived with your inner critic long enough, it feels like you.

It's not.

It's just a bunch of recurring thought patterns—unhelpful ones that can be changed.

The first step is recognising that a different way of thinking is possible.

2. Affirmation journalling.

Physically writing down positive words about yourself can feel awkward. But over time, it rewires your brain.

The key? Focus on qualities you want to expand within yourself.

Write them every day. Eventually your inner dialogue changes. It's like rewriting the script of how you see yourself.

3. Loving kindness meditation.

If meditation interests you, loving kindness meditation is another powerful tool.

It involves visualising yourself and others whilst repeating phrases of kindness and care.

Like journalling, it gradually replaces painful self-criticism with more positive mindset.

The choice—falling behind or being yourself

It's easy to feel behind in life.

Status games and an over active inner critic make it seem life is a race to be won—so we narrow our view and focus only on running the conventional path towards the finish line.

There is nothing wrong with the conventional path—many people live long and happy lives that way.

But we shouldn't assume it's for everyone.

And you should question whether it's for you.

A little over a year ago, I left a stable career in investment to start over in web design, development and digital business.

On paper, I'm falling behind—giving up years spent in an industry, a good salary, and stepping into the unknown.

But in reality, I'm following my curiosity, opening an exciting new chapter, and being intentional about designing a lifestyle that works for me.

There is lots I still have to work out and there a surely challenges ahead. But I feel engaged and excited to walk this unmarked territory.

You don't have to measure yourself against titles, ranks, or arbitrary timelines. The real game is about learning, evolving, and continuing to play.

So next time you are feeling behind in life, ask yourself:

• Am I really falling behind?

• Or am I just going in a different direction?

Because when you stop playing by every else's rules, you start playing a much more interesting game—one where progress is defined by you.

Thanks for reading and I hope this was helpful.

—James