Nathalie asked a question here that troubled me a lot before I quit my day job:
“How [do you] deal with friends/family who think you’re crazy to quit your job? (You touched on this in the “live your way” post, though more specific hints and actions to take might help too.)”
I was lucky enough that most of my family and friends didn’t think I was crazy, or if they did, they didn’t say so to my face. I had the support of the people who mattered: my boyfriend, Paul, and my parents. I don’t think any of them were exactly thinking “wow, what a great idea” when I first told them I was thinking of quitting, though – so I’ve got a few tips to offer.
For Nathalie, and for everyone else who’s stuck in a job that they’d secretly love to quit, here’s how to persuade your family not to hand you over to the nice men in white coats…
When Your Job Sucks
This is probably the only time you’ll see me say this, but if your job sucks, you’ve got an advantage.
I’m not just thinking about people with visibly awful jobs – I can’t imagine your nearest and dearest would think you crazy for quitting if you were scrubbing toilets for a living – but about jobs where it’s clear to those who love you that you’re miserable.
When I quit my day job, my family were quite relieved. Yes, the job paid well and was neither mentally nor physically taxing – but I was unhappy there. I suspect I’d never feel much like myself in a 9-5 job, but for me, the suckiness was mainly due to a couple of personality conflicts. My mum had wanted me to leave for a while.
So, if you’re miserable at work and your friends/parents/partner know it, you’re at an advantage. They’ll understand why you’re quitting – though, if you’re not jumping straight into the arms of another employer, they might have trouble getting their heads around you striking out on your own.
When Your Job Is Good
Sometimes, your job is actually fine. You don’t dislike it – you have friends there, you find the work enjoyable, you’ve got a comfortable routine – but something more is calling to you. How can you get family and friends to understand this one?
What I’m leaving behind is admittedly a middling (but respectable) career in publishing, but one, from the point of view of the working class people I grew up with, you just wouldn’t throw away. My parents didn’t go to college, and to them “pissing away” a decent salary is about as stupid a move as you can make.
(I Just Quit My Job… Am I Crazy?, Steven DeMaio, HarvardBusiness.org)
First off, don’t feel guilty for wanting more. I know that when I quit I felt like I was being selfish. I thought that loads of people would be delighted to have a job like mine, and that it was ungrateful of me to want to quit.
Of course, probably the least selfish thing to do was to quit and let one of those people have my job instead of me …
If you have friends in the workplace, this can be especially hard:
“I’ve been preparing for the last year to take the leap and escape the corporate train. My feet have gotten a wee bit cold as I think about handing in my resignation (my boss used to be one of my best friends at work before she became my boss but we’ve managed to stay friends and I feel like I’m letting her down).”
(Dianne, in a comment)
Remind yourself that your colleagues survived perfectly well before I joined the company – and that they’d manage find without you. However much people like you at work, don’t start thinking you’re indispensible. Of course, your friends will be sad not to have you around in the office any more, but they’ll be glad you’re off pursing your dreams.
When you talk to friends, family or colleagues about leaving, make it clear that you’ve enjoyed your job but that it’s time for you to move on to new challenges and experiences.
Telling Them #1: Staying Calm and Rational
However much you can convince yourself that you need to leave – whether because you hate your job or because you simply love something else more – there’s going to be a point where you need to tell other people about it.
The first step is to go into this in a calm and rational frame of mind. Yes, that’s easier said than done! Avoid getting defensive. Try to pick a good moment when things aren’t already fraught; blurting out “I’m quitting my job next week!” in the middle of an argument isn’t the best way to do it.
If you can, open up the conversation in a way that assumes the other person’s support. I won’t attempt to give you some cringe-making script for this, but you could use a phrase or sentence along the lines of:
- “I’ve been thinking a lot about my career recently, and I’ve come to some decisions. Of course, I know you love me whatever I do, but I’d like to talk to you about what I’ve decided…”
- “I’m really glad I can always count on your support. I’ve actually come to a big decision recently…”
In some cases, perhaps a specific event has sparked or furthered your desire to quit your job. This could be something negative (a health scare, a family crisis) or something positive (a new baby, growing success with your side business). You could open the conversation by talking about this: understanding the why behind your decision can help your loved ones to accept it.
To get most people on board, though, you’ll need to reassure them that you’ve thought things through…
Telling them #2: Offer a Back-Up Plan
For your own sake, as well as for the peace of mind of your family, you should have a back-up plan. This isn’t negative thinking. This is simply accepting that sometimes life doesn’t pan out quite how you’d hoped. A back-up plan can help you make the jump – and helps others to let you.
In many cases, you may want a couple of back-up plans: the if-it-all-goes-horribly-wrong plan and the if-things-are-a-bit-hairy plan. Mine were:
- If it all goes horribly wrong, I can just get another job. (Glib, yes, but I have a good degree and I live in London, where graduate jobs are in reasonable supply.)
- If things are a bit hairy, I’ll do some childminding. (Which I did end up doing, because the first few months of freelancing were slow, and it helped me ease into my new life.)
You may decide to spend some time or even money on maintaining skills or qualifications that would allow you an easy route back into your former career, if necessary:
When I left the law, I sat down with various members of my family and closer friends and explained what I was about to do and why. I also reminded them that I was still a member of the bar, that I would maintain my license to practice, and, worst case, could always go back and pick up where I left off.
(Jonathan Fields, Career Renegade – reviewed here, p 245)
Telling Them #3 – Don’t! Just Do It Anyway…
Timothy Ferriss suggests that it’s usually easier to ask forgiveness, not permission:
If it isn’t going to devastate those around you, try it and then justify it. People – whether parents, partners, or bosses – deny things on an emotional basis that they can learn to accept after the fact. If the potential damage is moderate or in any way reversible, don’t give people the chance to say no. Most people are fast to stop you before you get started but hesitant to get in the way if you’re moving.
(Timothy Ferriss, The 4 Hour Workweek – reviewed here, p33-34)
Now, much as I admire Ferriss’s chutpaz and confidence (The 4 Hour Workweek is an inspiring and energising read), I’m just not that confident! However, I wanted to include that quote here because you’ve got the balls to go ahead and quit, letting people deal with how they please, that may well be the best way to deal with potential nay-sayers.
I’m aware that I’ve had an easy ride; my family and friends were all very supportive of my plans. If you’ve had to talk to family and friends about quitting your job (or quitting anything, for that matter), or if this is something that you’ve thought about, I’d love to hear about your experiences and ideas in the comments.









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Nice tips Ali on how to deal with people who think you’re crazy for quitting your job. I’m going to school right now, but I like to blog. My parents probably have the opposite feelings compared to Nathalie, which is they think it’s crazy not to get a job and blog. So, then… how do you deal with crazy parents? (Just kidding). Hehe.
Tristan Lee´s last blog ..50 Random Moments to Value in Life
Can I just say first off, this is the best permalink you’ve ever had.
And second, I love both Jonathan Fields and Tim Ferris’ writing, so this article had me at “crazy-quitter”
I think staying calm and rational is a good call, but I think we should also look at the other side of it – other people are not to react emotionally too, so perhaps considering that (and not being too “rational”, which I have a tendency to be) might help smooth things over =)
Sid Savara´s last blog ..Personal Development Roadblocks – Pushing Pleasure Buttons
To be honest, it’s not an easy thing to quit ones job. Still, all successful people that I know quit their jobs. I admire your courage in following what you want in life, and I envy your family who is supportive of you.
Thanks Tristan. I think my parents felt pretty similar when I left my day job to blog (and write and some web stuff) full time … but now I’m making a living from it, they’re convinced!
I probably had an advantage over some folks cos I’d left home by then: if you’re still under your parents’ roof, it could be tricker.
Sid, cheers! I put all of ten second’s thought into that permalink. (More than usual, I should admit!) Jonathan and Tim are great – though my style’s a bit softer.
Good point about other people’s emotional reactions. I think, on reflection, “calm and rational” might not have been the best way to put it. I’m aware that my tendancy is to get defensive very quickly, so I guess that’s what I was cautioning against.
Walter, it is definitely not an easy step to take. I’m sure it’s possible to be successful *without* quitting your job – depends on your definition of success, after all! For many of us, though, the 9-5 world doesn’t come close to letting us live the lives we want.
I hear ya. It may appear sexy to some to work in large bureaucracies, but having spent an entire career in one and now transitioning to self-employment, I’m amazed that the lack of oxygen from being smothered hasn’t left me brain dead.
Jim´s last blog ..Generation Y’s Job Plight: Top 12 Tips for Gen Y
Again, another timely post! (and this time I’m only 3 days late reading!) I am a week off my ETD . . . mostly because of hitting a wall with my husband. But I am working through things, trying to understand his fears (he’s known this and seemed agreeable for a while but now is getting nervous I guess). The crazy thing is – we can absolutely survive on his income alone. It’s the lifestyle changes we’re facing (temporary, I might add) that seem to be part of it.
My point is there is always some underlying reason for the resistance. Taking time to step back and listen seems to help. Our society is not big on dialogue – we seem to prefer straight up answers – but asking things like, “how do you feel about XXX” is making a difference. I’m also asking for him to propose a compromise or alternatives. I think he’s seeing I do value his input and his feelings. I realize this is slightly different than just talking about the support of one’s parents or friends but nevertheless, good dialogue always seems to open doors. (dialogue actually means to talk through something – as opposed to “discuss” which has at it’s root the idea of beating someone over the head i.e. concussion!)
Good stuff – keep it coming!
Jim, congratulations on the self-employment move – good for you! (And well done on avoiding getting smothered, too…) Hope the transition goes well for you, and hope it’s the start of a lot of new and exciting things.
Dianne, kudos to you on having the patience and love to work things through with your husband. I’m sure that, even with all the practicalities – like paying the rent – accounted for, he’ll be anxiously wanting to be convinced that it’ll all work out well for both of you. “Dialogue” is a good word: sometimes our “discussions” can degenerated into a bit of a monologue…
Compromise, alternatives and, where possible, a win/win situation are great directions to take – thanks for broadening out the conversation to include these. I agree that feelings are extremely important and often underacknowledged: we tend to find it hard to articulate, even to ourselves, *why* we might feel resistance about something.