midlife family

Or are you being selfish? …. asking for a friend.

Your career helps keep your family afloat and your life stable. But a job takes up at least 8 hours of at least 5 days a week, and it may not be your dream profession.

When you’re looking over your career in midlife, the grass can very much look greener on the other side. The problem is, there’s a gaping canyon between you and the fresh career start you think you want. And as a Gen X-er, it’s likely that trying to leap to that greener grass will leave you and your family at the bottom of that canyon.

There’s a whole host of reasons you might be unhappy at work. Perhaps you’ve been doing the same type of work for two decades and are, quite simply, bored out of your mind. You might feel like people in other fields make more money than you or seem to be having a better time.

It may be that you’re not climbing the ranks as fast as you expected when you entered the field in your twenties. But this is not your industry’s fault – it’s possibly your lack of enthusiasm. If you’ve not been networking, building your skillset, and improving the value you add to your company (or your appeal to new employers), who owes you a promotion?

If the only seminars you attended were ones your managers forced on you, don’t be surprised when the promotions start landing elsewhere.

Your rational brain may be screaming at you – Don’t leap across the gap! You might get a pay cut! You’ll probably be reporting to a millennial! You’ll feel selfish for disrupting your family’s cash flow! Everyone the same age as you will be far more knowledgeable about what they do! A career change might not even guarantee you end up happy!

The teenager in you who watched one too many Bond movies flashes a peace sign at your rational brain, smirks, and hollers “YOLO” like a douchebag. “Tick tock, dude. Your time’s nearly up.”

Who do you listen to? Yes, you might feel that some invisible clock somewhere is running down. But the YOLO philosophy doesn’t hold all the answers, especially when it comes to your career. You do only live once – meaning you have one opportunity to avoid dragging the people you love off a cliff for your own gratification.

It’s always healthy to ask questions about your place in the world, the way you fill your day, and the decisions you’ve made. But if you’re looking for a career change during midlife, and you’ve got a ton of responsibilities, it might be time to look at those questions in a different light.

  • Did you set yourself career goals and establish a timeframe for achieving them?
  • Did you take your progression for granted and coast through professional life?
  • Did you take a wrong turn, but not necessarily head in completely the wrong direction? Is there time to correct the course?
  • Is it your career you really hate? Or is it your job, company, or manager? Are you really about to jeopardize your next three mortgage payments just because your manager’s an asshole?

Team Vippi is here to give you the splash of cold water you need. It’s time to wake the f*ck up and smell the bad filter coffee.

Why you think you want to change career – and why you should check those feelings at the door.

Don’t be like Milton and burn your career to the ground over a stapler – fix yours before leaving it.

You need to take a long, hard look in the mirror before handing in your notice and completely restructuring your LinkedIn.

“I wake up filled with dread.”

We say: Nobody deserves to wake up feeling terrible (except whoever’s responsible for the movie Howard the Duck). But if you wake up feeling sh*tty every day, you have to work out if that’s your career talking or something more.

Drill deeper. What is it about your work you’re having issues with?

“It’s the specific task I do.” No career revolves around one task. Put in a bit of effort to upskill or make a sideways move. If you’re in insurance, you might hate underwriting – so consider sales, brokering, loss adjustment, or claim fulfilment. There’s always a role that fits your personality better.

“I hate my company. There’s nothing stopping you applying elsewhere. Get your resume up to scratch, and put in the legwork. There are plenty of crappy companies – but plenty of diamonds in the rough, too.

“It’s just so boring.” Are you f*cking kidding us? Most jobs are boring at points. Even Madonna turned around in her heyday and said “Goddammit, guys, another conical bra? Give me a break.” If you’re bored, go take skydiving lessons. This is your career you’re talking about.

“I feel guilty about what I do.” Okay, this is actually a pretty good reason to dread waking up – but not a reason to leave all your expertise at the door and jump into the unknown. If you’re a defense lawyer keeping murderers on the street, you may have a few sleepless nights. 

Don’t just resign from the BAR association, then. Learn about how to become a copyright, corporate, or prosecution lawyer.

Our point is that you shouldn’t wake up feeling terrible every day because of your job, but there’s always a way to change your path within a career. Every field is wide enough for wiggle room.

“I constantly feel like I forgot something – my brain is always busy.”

We say: If you change career, you’ve made an extremely risky decision with no guarantee that your brain won’t be as occupied in your chosen field, if not more so.

You think about work all the time, sure. That’s the case with most people. But your brain is likely full because:

  • You’re constantly multitasking.
  • You never manage your priorities.
  • You’re thinking about things outside of work that need addressing.
  • Your company are pr*cks and have no regard for your mental health, so they keep cranking up your workload.
  • You resent what you do, so negative emotions are taking up brain space and draining your energy for rational decision making.

There are countless ways to correct these problems, including taking a course in priority management, questioning your mounting workload with higher-ups, and addressing some pressing issues in your personal life.

Ditching your career isn’t the answer here. Imagine how preoccupied you’ll be when you change career and all of these problems follow you. Fix what you need to fix in your approach.

“I’m just not living my dreams, man.”

We say: Because you and your employer aren’t supposed to be in your dreams! This is the real world. It’s built on blood, sweat, sacrifice, and unappreciated effort. Nobody pays you a salary to sip Sangria on a f*cking yacht.

You can follow your feelings, sure – but are you really about to abandon your responsibilities to make an emotionally-driven decision? What if your partner decided that you weren’t their dream match after watching a rerun of George Clooney in ER or Sharon Stone in Basic Instinct, and left you based on a ‘gut feeling’ that they could do better?

Maybe you could do better if people weren’t depending on you – but stay in your lane. This is how you make money and account for your responsibilities. Be clever about adapting it into something you can at least tolerate or control better.

“But my boss suuuuuucks.”

We say: Loads of bosses suck. Imagine how disappointed you’ll be when you turn up to the first day of your new career, and your new boss sucks just as much – but now you’ve lost all your stability on top of any other problems you had.

We know that one horrible boss can ruin your day. They don’t listen, undermine you at every turn, and micromanage you so severely that you can’t get your job done.

Maybe you’re at the wrong company, then, instead of in the wrong career. Perhaps it’s not even as dramatic as that – maybe you simply need to switch teams within the same company to avoid a toxic professional relationship that’s creating roadblocks.

Here’s how to try and rectify that:

  1. First off, try setting up a meeting with your boss, and be frank with them. You’d be surprised how many superiors appreciate an upfront approach. If you’ve sat in your cubicle, feeling resentment for 5 years without saying anything, what do you seriously expect to have changed?
  2. If that doesn’t work, escalate the query through HR, or check for internal transfers. Maybe you can switch to a different team or department.
  3. Failing both of those options (because not all HR departments are effective either), look for a job elsewhere. It might be time.

Nowhere in that list do we suggest that it makes sense to go all the way back to square one.

“I’m not progressing like I feel I should.”

Don’t be a baby. Put the effort in.

We say: How on Earth is that your career’s fault? Can you imagine if Edmund Hillary got halfway up Everest, turned back, and gave the excuse that it’s the mountain’s fault for being too big? Cry us a frickin’ river.

Businesses run on value. If they provide products or services that customers deem to be valuable, they sell their wares and stay afloat. In the same way, a company keeps you on their books and rewards you for being valuable. You’re not progressing because you haven’t taken the time to add enough value to your current employer. 

If you don’t work to progress, you’re not keeping your value static – you’re actually losing value. Never underestimate the competition. There’s someone hungry for your job who can do it better, show more enthusiasm, and possibly, desperate enough to provide their services for less money.

So many midlifers in the professional world build their reputation on time served rather than value added, then get surprised when they haven’t gone anywhere. If people picked sexual partners based on the time they’d been alive rather than the characteristics they bring to the relationships, yours would’ve left you for one of your grandparents long ago.

It. Just. Doesn’t. Work. Like. That.

Take five minutes to think about your actual goals. They might be direct like a financial goal, or vague in a way that just has sweeping ambitions, but sit down and map out your short-, medium-, and long-term goals. Think about why you haven’t met them or aren’t meeting them.

Instead of putting absurd levels of energy into finding an entirely new field of employment, why not take a course or attend industry-specific workshops?

As a starter, just connect with a few people on LinkedIn and have some conversations about the steps they’ve taken to progress. You can search under the job title you’d rather have and spark up some chats with people who’ve gotten there.

You’re doing that thing where you put in zero effort and expect results. So certainly don’t burn down your career – you’re only making more effort for yourself. Instead, exert your effort in the right direction.

Do you feel like changing careers because you think you’re owed a promotion?

Many folks in our generation feel like they’re owed a promotion. You expect to do a job for a few years, move forward, boss a few more people around for a couple more years, progress again, rinse, and repeat, before retiring with a nice, shiny smile on your face.

That isn’t how it works anymore. If you’ve not been promoted, an HR professional on LinkedIn recently explained why that can be the case:

  • You haven’t asked your manager about it.
  • Your manager can tell you’re in the wrong job, but you’re too comfortable to have noticed. (Note: That’s the wrong job, not the wrong career.)
  • You haven’t established the steps necessary to get promotion because you felt it was coming to you anyway.
  • You’re too arrogant to believe or accept the feedback you get on your work. So you’ve done nothing.
  • You’re complacent and simply think “it’s time”. But time doesn’t earn the money – your added value does. Not enough value, no promotion.
  • You adjust how much work you do based on your (clearly negative) feelings about your job. Your manager sees this.
  • You place your career ambitions over the needs of the company, and that doesn’t go unnoticed.
  • You’ve got no idea how to step up your productivity or skills.
  • You’ve only been thinking in terms of “forward” steps and not “sideways” or “diagonal” steps into a more suitable role.
  • You haven’t been promoted so you’ve mentally checked out.

The way to get around this is to be CASUAL:

  • Communicate with your boss. Ask what’s blocking the promotion.
  • Act on the feedback you get.
  • Stop being complacent or big-headed.
  • Upskill all you can.
  • Add value where you can
  • Let your work speak for you.

No company owes you their hard-earned turnover. Justify your promotion by adding value.

“I’m just not finding balance in the rest of my life.”

We say: You might pin that on a demanding boss or a company that sets high targets. But, again, that’s not the career – it might be the company or the level you’ve reached. It might even not be work at all, but elements of your personal life. We sometimes misdirect why we feel like sh*t.

Unconsciously, you might want to start a new career because you miss how easy it was at the beginning. And perhaps it was easier then because you were younger, received more professional guidance, had fewer personal responsibilities, and were naturally more eager to learn.

You feel like that’s going to take the pressure off – but we guarantee you it won’t. What you’ll lose in corporate pressure, you’ll gain in personal and financial troubles. The stress will double because you’ll have no safety net, and your new career may still be as demanding. 

Balance doesn’t just come from the career you choose. It comes from the parts of life that don’t earn you money. Don’t run away from your obligations. If your life is unbalanced, make the non-work parts of your life richer by investing in your personal development and relationships.

If your job truly is a time-suck – let’s say you’re an ER surgeon doing 14-hour shifts for weeks on end – don’t leave your industry altogether. Maybe look at becoming a consultant or moving into a different field of medicine. But don’t blow 7 years of medical school on a random whim if people are relying on you.

“I still don’t feel like I’m good at what I do – or it doesn’t feel good even though I’m competent.”

We say: Oooookay. There are two elements to this:

  1. You’re not as good as you should be.

Then upskill, modernize, and move with the times. Consider a sideways move. And accept that even if you become good, you might not get much out of what you do – but you are good at it and can support the people you love by doing it.

Udemy, for example, is a fantastic platform that offers a whole range of online courses you can use to learn new skills. Speak to your manager or HR about what courses they’d recommend – who knows, they might even pay for it.

  1. You’re good at what you do, but it doesn’t fulfil you.

Sure, but does your lifestyle fulfil you? Does the roof over your family’s head fulfil you? Do your holidays, your childrens’ birthday gifts, and your security fulfil you?

There’s truly no job that’s 100% fulfilling. And if you don’t believe us, ask Britney Spears, Michael Jackson, Brian Wilson, or any other popstar who “lived the dream” but ended up ruined.

Even then, is it really the task at hand you hate? Maybe your company doesn’t invest enough in employee culture and morale. It might be time for that level of change, sure. Just not a whole career shift.

“I earn a lot, but I also cry a lot.”

We say: That’s… not good. At all. But is that your career’s fault?

If you’re always upset, maybe you need to self-examine and work out whether you have depression or need to build resilience. If everything else in your life is great, your company is friendly and supportive, and your colleagues are your best friends, then yes, it probably is your chosen career.

However, we strongly doubt that’s the case. A high salary doesn’t always make for emotional security.

You might need to seek professional help. Speak to a psychotherapist or counsellor, and they may be able to help you decode your feelings and get to the root cause before you make a dramatic and risky decision like a career change.

“I get so jealous when I think about other people’s careers.”

career change

Not everyone can be a rockstar – but you’re one to your family. Don’t lust after other people’s lives.

We say: Stop it. Right now. Jealousy is ugly and misguided. Your friend might be a millionaire poker superstar or TV personality, but they might be jealous of what you have with your family. 

Focus on your own sh*t and let other people do their own thing. Gratitude is a choice.

This isn’t you hating your career. You’re just being an ungrateful asshole. Take stock of what you have, take a deep breath, and get a grip.

“I distract myself with excess booze, drugs, or endless TV/mobile doomscrolling.”

We say: This might point to a deeper problem than your career choices.

There are countless reasons that substance misuse or a sedentary, phone-addicted lifestyle have taken hold of your life. And it might be addiction that’s driving you to make risky decisions like leaving your career.

Do not make these decisions without a clear head. How about this:

Make yourself a deal. If you seek help with recovery or find ways to add depth and meaning to your personal life, and you still find that your career is the root of all your problems, then you can make the switch.

We can almost guarantee that some other demon is driving the bus. The effects of substance misuse always reach beyond the person it’s happening to, but making a decision like this could have a real, lasting impact that shatters your security and relationships.

“I don’t get to be myself while I’m in the office.”

We say: Come on, now. It’s your choice to avoid being genuine. If that means you’re upset that you can’t make non-PC jokes in the break room, that’s a truly sh*tty reason for changing your entire working life with no safety net.

Instead of looking into new career paths, think instead about how you code-switch into your professional personality. Everybody has a code-switch. Code-switching refers to how we change the way we talk in different social environments. You don’t talk to the barber the same way you talk to your parents, and you most likely turn on your Ps and Qs when you’re in the office.

Yes, you’re more polite, but there are ways to avoid leaving your personality at the front desk when you check in.

What are your positive qualities outside of work? Are you kind, helpful, considerate, and funny? If you carry those over, but have to ditch the genital jokes you drop in your WhatsApp thread, you’re still “being yourself” – just not all of yourself. And that’s fine. No one is 100% themselves in a professional environment.

Authenticity doesn’t mean assaulting all people with your whole personality all of the time. Otherwise you’d send the same dirty texts to both your partner and your parents. Which… eww.

You get to decide how to present yourself in different situations. Even if your office doesn’t allow for much casual chatter, choose to embody certain values at work. You might not be allowed to cuss in the office, but you can still talk to your colleagues about your personal life and make subtle puns during your office breaks. Just use common sense.

“I don’t talk about my career.”

We say: What you mean is you don’t brag about your career. But who likes those people anyway?

Maybe it’s not a “cool”, interesting job, and you think no-one cares. So try finding like-minded people – it’s called networking. It’s easier than ever on sites like LinkedIn. Whatever industry you’re in, there are seminars and events full of people dying to talk about the latest news and developments in whatever you do.

If you’re not particularly excited about your job, build yourself an online or in-person network before you move companies. Get as much insider info as you can. Make HR departments across the field aware of you. Find out what working there is like before applying.

If you can’t swim, you wouldn’t jump into a pool without knowing the depth of the water. So have a chat with as many lifeguards as you can.

You keep trying to make it work and it never does.

We say: Maybe your career is not the problem. Maybe it’s you. How do you define that it’s “working” though? You cartwheel into work every morning with glee? You get crowned CEO of the company? What does a win look like for you?

We get that it can be extremely frustrating to tread water. Sometimes, you have to face a thousand failures before achieving the success that defines your professional life.

You know who has the most missed field goals in the NBA? Yep – Kobe frickin’ Bryant (RIP). He’s one of the best ever because he wasn’t afraid of failing over and over and over again. So:

  1. Set your targets.
  2. Talk to people that can help you reach them.
  3. Act on their feedback.
  4. Exceed your own expectations.
  5. Reward yourself.
  6. Set new, higher targets.

Restarting your career is just going to set you back years rather than getting you any closer to ‘making it work’. 

You feel completely apathetic about your job.

We say: Just care more, then. Fully invest yourself in moving forward. Or, care less, compartmentalize your work life, and focus on the great things it helps to facilitate for your family.

We all have to make sacrifices. You might not care about the plot details of your child’s school play or filling out your tax returns, but if you attend to neither, you’ll be in trouble with your partner or arrested. (Which is worse? We couldn’t possibly say.)

How to switch careers if you’re unhappy

Once you’ve self-assessed (using a tool like a SWOT analysis to calculate your strengths), and if you truly feel that changing your career and disrupting your stability is the right move, you have to make the switch in the smartest way possible. 

Ask yourself 5 questions to set yourself on the right career path:

  1. What specifically makes you unhappy in your current role? Is it your company or colleagues? Does your boss bully you? Is it your office culture or the job itself? If you did the same job somewhere else, would you still feel the same level of dread?
  2. What attributes of your current role would you like to take with you? You might not like the specific duties of your job, but find the surrounding industry fascinating. You might love connecting with people and interacting with customers, but hate sales – so maybe customer services is a better fit in the same company. Every job has elements that suit you, otherwise your employers wouldn’t have picked you and certainly wouldn’t have kept you. What are the elements you want to hang on to?
  3. What are your core values? There’s no right answer. Are you a natural fixer? Do you thrive on ideas and innovation? Are you more centered around community and helping others? Have a deep and honest conversation with yourself about what’s really meaningful in your life. Any career built around anything other than your core values isn’t likely to make you happy. These will help guide you to the right career.
  4. What are your strengths and what do you need to learn? You’ve been doing a different role in a different industry for many years. What are the gaps in your experience you need to fill? You may need to return to school. You can also try to build a portfolio through side gigs or apply for internships.
  5. What are my short, medium, and long-term goals for moving into my dream career? Put your plan in motion. Short term goals might involve taking online courses, networking with industry professionals on LinkedIn, or attending relevant workshops and seminars. Medium-term aims might involve applying for internships, applying to industry agencies, and relating your profile and portfolio more to your dream career. Long-term goals should, it goes without saying, involve working in your dream field. If there’s a specific company you want to work for, work out how.

See? It’s not easy. At all. You could address many of these points by making a horizontal move in the same company, moving to a different employer, or tweaking the field you’re in to better suit your personality.

“I don’t feel like anything I do at work really makes a difference.”

We say: Have you actually asked about how to make a difference in your workplace?

Companies are always looking for ways their people can step outside of the role and contribute to the wider operation. It literally saves them money if you do so.

It also pains us to say that you might simply need to get better at your current job. If you haven’t had the drive to ask about ways to make a difference to your employer’s bottom line or culture, you probably haven’t upskilled enough to make that difference.


tough love

Phew. Enough tough love for you?

Do the right thing for you, your family, and your career – shape what you have instead of burning it to the ground to build something new. Look at what happened in 2020. How many people lost their footing and ended up being out of work? Build on the security and foundation you have created.

Remember, there’s always someone out there dying to show your boss that they can do what you do, only better. Whenever you wish that you were somewhere else, keep in mind that there are others who wish they were where you are.

We’re not saying any of this out of spite. Team Vippi wishes only happiness and success for you and equally so for those who rely on you. But we also know that neither happiness nor success come easy, and that ducking out at the final hurdle is not going to bring them to you.

Article resources

6 signs it’s time to change careers. (2020). https://www.northeastern.edu/graduate/blog/6-signs-time-change-careers/ 

NBA & ABA career leaders and records for field goals missed. (n.d.). https://www.basketball-reference.com/leaders/fgx_career.html 

Time for a career change? 11 uncomfortable signs you need to make a shift. (n.d.). https://www.careershifters.org/expert-advice/time-for-a-career-change-11-uncomfortable-signs-you-need-to-make-a-shift