6 Questions Worth Asking When The Life You’ve Worked Hard For Isn’t The Reward You Imagined

When the life you built stops feeling like the life you want, these six questions help you understand what needs to change.

Online discussion forums are full of people who woke up one day and realized that the lives they worked hard for weren’t what they envisioned.

Instead of feeling happy, fulfilled, and accomplished, they simply feel lost or disappointed.

Some people refer to this as a midlife crisis, when in reality, it’s accepting that the road you’ve taken led somewhere you don’t want to be.

If you’ve been feeling like this, you’re not alone. Let’s look at some questions that may be worth asking as you figure out what your next steps should be.

1. “If I am in this same position a year from today, what will it cost me?”

When I asked myself this question, I was quite shaken by the answer my subconscious gave me.

Instead of a clear answer that gave me ideas of what actions I should take next, I simply started shaking.

On a soul-deep level, my entire being balked at the idea of still being in that situation in a year’s time.

I knew I could endure it a little longer, but if I had to stick it out for another 365 days, it would have cost me my health, my emotional wellbeing, and possibly even my sanity.

Epiphanies like these aren’t easy to deal with, which is why so many people prefer to avoid asking themselves these sorts of questions.

After all, once the answer is in front of you, you’ll have no choice but to fling yourself off the metaphorical cliff and hope that you’ll soar, or resign yourself to the claustrophobia of maintaining a life that’s making you unhappy.

I’d be lying if I said that upending my life was a simple thing to do. It was harrowing in many ways, but also led to me being able to experience some truly wonderful things. And what’s more, it helped me realize that I can handle anything life throws at me.

2. “Have I been living this way for myself, or to make someone else happy?”

Countless people spend their lives making those around them happy rather than pursuing their own dreams and goals.

Even though they may have lives full of things that bring them stability and contentment, that doesn’t mean that they’ve attained the reward(s) they imagined they’d have at this age.

For example, a person might spend decades earning a great salary, supporting their spouse, and raising their children, with the hope that they’d spend their autumn years in quiet comfort.

Now, however, they’re expected to take care of their grandchildren, tend to their elderly in-laws, and do volunteer work that they don’t have the energy for.

If any of that sounds familiar, ask yourself if you’re doing these things because they fulfil you, or because others expect all of this from you.

3. “If I could go back and do it all over again, what would I change?”

Many of us daydream about what our lives might have been like if we had taken different paths.

Even if we’re fairly content with our lot, we may regret the alternate lives we never lived and wonder what we would change if we could go back in time and make different decisions.

Asking yourself what you would have done differently can give you some strong insights as to what you can change in your current situation.

For example, you may not have chosen to marry your spouse. Of course, you can’t go back and undo decades of study or marriage, but the answer you come up with will give you some ideas about where you want to go from here.

4. “What would I find rewarding instead?”

Think about stories you’ve read or heard about in which people were doing things that you admired, or even dreamt of doing yourself.

You know what I’m talking about: the ones that left goosebumps of exhilaration down your arms and had you daydreaming about what it would be like to experience those things firsthand.

Now ask yourself what it would take to get you involved in those things.

In midlife, we aren’t all as physically healthy or capable as we were when we were younger. Namely, many of us struggle with health issues that might impede us from spending months on Sea Shepherd boats or trekking through the Himalayas.

But that doesn’t mean we can’t pursue things that will fill our hearts and souls with joy. For example, as much as I’d love to, I know I’ll never be able to be a field anthropologist, but I can still assist on digs, do research, write papers, and share my findings for others to enjoy.

5. “What small action can I take to better align with my goals and values?”

If you aren’t able to make big changes in your life for various reasons (i.e., financial or familial constraints), focus on something small instead.

The idea behind this is that many tiny changes will eventually lead to significant change.

Think of it like making small adjustments to your steering wheel while driving. You don’t need to yank it all of a sudden: those small adjustments will add up to you going in a completely different direction than where you were initially heading. It’ll just be a gradual shift rather than an abrupt turn.

If your life isn’t offering you the reward you imagined, and you have a firm idea of which changes need to be made, do something small that’ll help to get you there.

For example, if you know that you want to live somewhere completely different, start a savings account today.

Your next small action can be as small as a vision board with all the things you’d like to do to help you achieve that goal. Let that board inspire your next small change, as well as the one after that.

Just make sure whatever small action you take is wholly dedicated to the life you want to pursue.

6. “What good can be salvaged from this?”

If you’ve been working hard for several years only to discover that the life you’ve strived for isn’t the one that fulfils you, ask yourself how you can salvage some good from what you’ve accomplished.

Quite simply, how can you redirect or restructure what you’ve earned in order to attain real happiness instead?

A perfect example of this is a friend of mine who, now that she’s in her early 50s, realizes that the life she’s worked so hard for isn’t bringing her fulfillment or joy.

She’s divorced, has spent the past 30 years working as an accountant, and most of that was in a small, windowless office that smelled of mothballs.

She bought a house several years ago that’s now worth significantly more than she paid for it, and she also has retirement savings accrued.

As such, she has decided to sell her house and buy a flat in Portugal, where she’s going to retire early and spend the rest of her days making pottery and eating seafood, surrounded by rescue cats, never wearing high heels or lipstick ever again.

You’re never starting entirely from scratch. There is always something good that can be salvaged, even if it’s just knowledge and life experience.

Final thoughts…

If the life you’ve worked for doesn’t offer you the reward you imagined, change it.

This won’t be easy to do, and may cause significant upheaval in your life.

Those around you may not understand why you’re giving up a “dream life” in favor of something less stable, but they don’t need to understand why you’re doing what you do. They don’t even need to support your decision.

Your life isn’t over: you can still change direction, but doing so will take resolve and courage.

Which you have.

Do what you need to do to restart your beautiful life. Starting with one small step today.

About The Author

Catherine Winter is an herbalist, INTJ empath, narcissistic abuse survivor, and PTSD warrior currently based in Quebec's Laurentian mountains. In an informal role as confidant and guide, Catherine has helped countless people work through difficult times in their lives and relationships, including divorce, ageing and death journeys, grief, abuse, and trauma recovery, as they navigate their individual paths towards healing and personal peace.