Not where you thought you’d be by now?

“I feel like I should be further ahead by now.”

Said by an executive leading a FTSE 100 company. Said by the co-founder netting over £1 million by the end of year one. Said by the senior director who has just become a Dad. Said by a private banker who has just been made redundant.

As a coach, it’s my job to shut off my own head, beliefs, values and dialogue and really tune into the world of my client. Good thing too, because with each of these men, it would be very easy for me to assume they are winning at life (minus the redundancy).

They’re intelligent, driven, some self made. They’re credible, sought after, admired. But still, there’s this lingering sense that they’re somehow behind

Behind who exactly? Often, they’re not even fully sure. And where are you meant to be? That’s often even less clear.

But the feeling is there nonetheless.

Sometimes it’s triggered by a former colleague announcing a big promotion on LinkedIn. For one client, it was a friend selling a business. Sometimes it’s simply scrolling social media late at night and quietly absorbing everybody else’s carefully edited highlight reel while sitting in your own very normal reality. And that’s the part I don’t feel we really talk about enough.

Most of us now spend huge chunks of our lives unconsciously comparing ourselves to other people. We scroll constantly. Promotions. Fitness transformations. Career milestones. Expensive holidays. “Humbled to announce…” posts. Founders celebrating exits. Men our age apparently waking at 5am to meditate, invest, train for ultra marathons and build six businesses before breakfast. Frankly, that sounds exhausting.

Even when we know intellectually that social media is curated, polished and selective, it still lands somewhere psychologically. It tends to drip-feed quietly into how we see ourselves. You start questioning your own progress, decisions, pace.

And suddenly, what felt perfectly acceptable five minutes earlier now feels inadequate. And that feels nagging and uncomfortable.

Of course, comparison didn’t begin with social media. Most of us have been conditioned into it for years.

School taught us to measure ourselves against others, then careers did the same.

Salary brackets / Job titles / Promotions / House purchases / Relationship milestones.

By the time you reach midlife, comparison has often become so deeply wired that you barely notice you're doing it.

The problem is that midlife changes the emotional weight of comparison altogether. There’s often a growing awareness that time is no longer endless. For some men, there’s a sense that they’ve now been in their career longer than they’ve got left in it, and with that comes expectation — usually self-imposed — that they should be at a certain level, stage or financial number by now.

20 year old you might have thought

“His career looks impressive.”

But 48 year old you might look at the same reference point and be asking

“Have I used my own life well enough?”

That’s a very different question.

And it’s often why comparison hits much harder in your forties and fifties than it did earlier in life, particularly for high-performing men who have built much of their identity around achievement, capability and momentum.

What complicates things further is that the goalposts keep moving.

In your twenties, success might have been getting the job. In your thirties, it may have been progression, status, income or building a family.

But eventually many men arrive at the place they once thought would make them feel secure or fulfilled… only to discover the feeling doesn’t last very long.

Because there is always somebody earning more, building faster, achieving younger, living differently.

And without realising it, many of you will have begun measuring your entire lives against people you don’t even know particularly well. And in many cases, against lifestyles you don’t actually want when you stop and think properly about it.

That’s the trap.

There’s a really interesting book I read recently called The Gap and The Gain, which speaks directly to this mindset. In summary, if we choose to measure our success from the gap, we focus in on what we haven’t yet done, or still needs to happen in order for us to feel fulfilled/ successful / enough / done.

If, on the other hand, we measure our growth / success/ fulfilment based on the gain, we are looking back at how far we’ve come to get to this point. We measure the experience gained, the promotions, the bravery, the milestones. “Less ‘I’ll be happy when’ and more ‘look how far I’ve already come.’”

COMPARISON ISN’T ALL BAD

Comparison itself is not inherently unhealthy. Sometimes it can inspire ambition, growth, standards or possibility.

The danger comes when comparison quietly shifts into self-judgement.

That internal voice that says:

• “I should have done more.”

• “I’m behind.”

• “I’ve missed my window.”

• “Everyone else seems to have figured it out.”

Because once that narrative takes hold, it can affect decision-making, relationships, risk tolerance, presence and self-worth. And ironically, it often pulls you further away from the life you genuinely want because you become overly focused on chasing somebody else’s version of success.

One thing I’ve noticed repeatedly in my work - many of the people being compared against are not nearly as fulfilled, confident or certain as they appear externally.

The human mind is very good at removing context, particularly when we’re already in a doubtful or self-critical headspace. Because we don’t see the anxiety, the pressure, the trade-offs, the relationship strain, the exhaustion, the loneliness, the uncertainty.

And yet many men compare that external snapshot (whether on or off social media) to their own full internal reality, which is always going to feel like an unfair fight.

Perhaps the more useful question is not:

• “Am I ahead of everyone else?”

But:

• “Am I building a life that feels aligned with who I am now?”

• Are you working towards what fulfilment looks like to you?

Because success at 45 may look very different to success at 30, and rightly so.

For some men, success becomes more about health, family, freedom, presence or playing a lot of golf rather than endless accumulation and proving.

And that shift is not failure, it’s maturity. It’s a shift in values. Although it can take many a surprisingly long time to give themselves permission to see it that way.

FINAL NOTE

Comparison will probably always exist to some degree - we’re human. But the goal is to notice when you’re drifting into it without automatically believing everything your mind tells you in those moments.

Pause, and ask yourself:

Is this comparison even relevant to my life? Do I actually want what they have (with the side note, we don’t actually know what their reality is)? Or have I just absorbed somebody else’s definition of success without questioning it?

Because feeling behind does not necessarily mean you are behind. Sometimes it simply means you’ve stopped paying attention to your own direction and become too focused on everybody else’s pace.