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Top 5 Career Regrets

I know I talk a lot about money and being financially independent as soon as possible but having a career, and having a life is not about living for the money and working like a dog.

(Unless you really love doing that, then by all means….. would you mind sending me a cheque? 🙂 )

You have to enjoy the job you are doing as well, seeing as you spend 40+ hours a week at it.

There is no point in having all of that money in retirement if you suffered, and felt miserable through the majority of your life to get it.

Be happy with your lot, or change and find something that may pay less, but will make you 10X happier.

This is why Harvard Business Review’s Top Five Career Regrets struck such a chord with me. I’ve taken quotes from each regret:

Career Regret #1: I wish I hadn’t taken the job for the money

Lamented one investment banker, “I dream of quitting every day, but I have too many commitments.” Another consultant said, “I’d love to leave the stress behind, but I don’t think I’d be good at anything else.” Via

Career Regret #2: I wish I had quit earlier

Said one sales executive, “Those years could have been spent working on problems that mattered to me. You can’t ever get those years back.” Via




Career Regret #3: I wish I had the confidence to start my own business

Even Fortune 500 CEOs dream of entrepreneurial freedom.

Admitted one: “My biggest regret is that I’m a ‘wantrepreneur.’ I never got to prove myself by starting something from scratch.” Via

Career Regret #4: I wish I had used my time at school more productively

A biology researcher recounted her college experience as being “in a ridiculous hurry to complete what in hindsight were the best and most delightfully unstructured years of my life.” Via

Career Regret #5: I wish I had acted on my career hunches

In 2005, an investment banker was asked to lead a small team in (now) rapidly growing Latin America. Sensing that the move might be an upward step, he still declined. Crushingly, the individual brave enough to accept the offer was promoted shortly to division head, then to CEO. Via

Via Harvard Business Review: Read the entire Top Five Career Regrets in detail here.

Pretty powerful, no?

Here’s my take:


Instead of focusing your energy on getting more income, why not focus it on seeing how LITTLE you can spend for a comfortable life, so you can have a wider range of career possibilities?

If you spend a lot of money, like $80,000 a year because you have a house, 2 cars, and all the trappings of a middle-class existence, then you will be forced to stay in that job forever.

But if you change your spending habits and only spend about $30,000 net a year, you only need to make about $48,000 gross.

What jobs and careers open up for you then?


Not everyone wants to do it, so don’t focus on it being the solution if deep down, you know you don’t want to be on your own.

It is NOT an easy life to be your own boss, to own your own shop or business and to be the only person accountable for every damn thing including making sure you have enough money to survive through the tough years.

It is a Feast or Famine lifestyle.

I know at least 2 freelancers who became their own boss, rather liked it for the money at the time, but then re-joined a company at the end of it all for various reasons:

  1. Had no idea how to create a budget and stick to it
  2. Had no savings & spent every penny they earned & when the famine hit, they starved into debt
  3. Preferred a stable career with a manager, a structure, colleagues and the whole 9 yards
  4. Didn’t want to be a Lone Wolf (many freelancers are fiercely independent Lone Wolves…a hard life)


I can safely say that I’ve avoided turning all of the above Career Regrets into Lifetime Woes.

Hit all of them.

At school, I didn’t work THAT hard once I got into business school, partly because I was working 2 full-time jobs to stem the pain of student debt, so I sort of enjoyed those years (Avoided Regret #4).

Then I literally took the best-paying job for the money to clear my loans (Avoided Regret #1), and by luck, ended up loving it.

I couldn’t take dealing with managers any more, so I quit after a few years (Avoided Regret #2), and found my own way in the industry by starting my own business (Avoided Regret #3) by acting on my career hunch (Avoided Regret #5).

It is never too late to change, but it will always be too late for regrets.


  • Sarah Li Cain

    I hit #1 about 6 months ago when I first moved to the states. I had to leave because the company’s values just didn’t click with mine, plus I had someone who stalked/harassed me AND my husband when he would come by the office to meet me for lunch. I also agree with never say never. I said I would never return to Asia after living there for 5 years, but am now making the transition back to start a business there in a few years. Yikes!

  • Bridget

    Couldn’t have come at a better time. Thanks for the kick in the pants 😉

  • Mo' Money Mo' Houses

    I hate having regrets, but I definitely understand not taking certain career opportunities because you’re afraid of risk. But sometimes the best things in life are things you are afraid of. Great post!

  • Jacq

    Ha on the Dilbert. I called the woman I report to today “my pointy haired boss”. She was like “am I?” and I said “yes your obsession with the font size of bullet points (like the little dot, not the words behind it – well, those too but…) is ruining my life. And your hair is kind of spiky today. This is why I don’t want to work in this company.”
    Sadly won’t get fired / contract terminated for insubordination. A girl can dream…

    Here’s the thing though too – if you like where you are and what you do, you do a good job, aren’t cranky and don’t insult your bosses. I really have had several jobs where I was as happy to go into work on Monday as I was to pack it up on Friday (or Saturday). Or work all weekend. For me it comes down to autonomy and non-routine work. Can’t stand micro-bullet point-management or doing the same thing every month and never could. I build the systems and other people that can stand that kind of thing use them. It’s a win win.

    • Mochi & Macarons

      *LAUGH* That’s a dream job. Not being fired for being outspoken and being insubordinate? 🙂 Lucky.

      You’re right about the micromanaging. That is probably the worst of any job I have ever been on.

      Or the constant hand-holding which is just another form of micromanaging.

      • Jacq

        Hmm I don’t know if I’ve ever had my hand held. I think I would slap them.
        Well… people get used to my sense of humour and don’t-give-a-f***edness pretty quickly. Hello? Elephant?? There in the corner – don’t you see it??

        Needless to say, I work best alone. 🙂

  • My Shiny Pennies

    About a year into my previous job, I applied and was accepted into a top master’s program for library science. I quit my job shortly after and was a month away from starting school when I got a call from my former employer. They had fired my former boss and offered me the job. I accepted, basing my decision primarily on the pay increase. I still think back on my decision every now and then, which tells me this job isn’t what I wanted afterall. I may go back to school someday, but I’m too scared to make that leap right now. The courage I had two years ago is gone.

    • Mochi & Macarons

      But do you hate it?

      The key is not necessarily to love the job like you want to do it as a hobby or would do it for free. That’s ideal, but the second best option is you have colleagues you love talking to, a work place that is fair and just, and the work is not stressing you out.

      • My Shiny Pennies

        I don’t dread going to work, but I strongly dislike what I do. I agree that one shouldn’t expect to love a job because expectations that high are hard to meet. I’m just feeling that this may not be the right line of work for me.

  • PK

    Here’s a theoretical: how often are titles valued versus the money? Consider a boss with an all-star sales staff making more money than her – Is the CEO title all it’s stacked up to be?

    When I look at freelancing, I laugh at the “be your own boss” bit. That isn’t true unless you’re financially independent. Truth is, if we’re working, we’re working for someone – whether it’s Mr. Smith or Google AdSense.

    • Mochi & Macarons

      Yes. A CEO title makes people feel a lot better than someone who makes more money.

      If that weren’t the case, why aren’t there more people in trades, making 6-figures a year, driving a truck or working in construction sites?

      They prefer having a desk job and a ‘title’ to go with it. That’s also why companies promote people to random managerial titles, pushing on 30 hours more of work a week (almost 40 hours), but with only a $5k – $10k bump in salary.

      As for freelancing, the ‘be your own boss’ bit for me works because I really only have to answer to the client which is fine because I’ve always been great with clients.

      I don’t have to fill out stupid performance reviews, come into the office on my benched days, chit chat with people I don’t like, kiss ass, be at the mercy of the whims of someone who wants to send me off to some remote place to work, etc.

      Or work on the weekends “helping” other employees for free or coaching them.

      Right. That’s going to happen.

  • Do or Debt

    What a great post! I don’t have many of those career regrets. Mine have mostly been leaving my career for grad school. I am hoping it will pay off someday. I do wish I networked more in my positions, and am interested in being a freelancer, but I also like structure so don’t know if it is for me.

    • Mochi & Macarons

      If you like structure, being a freelancer is not for you. I can tell you that right off the bat.

      You have to find your own contracts, do your own hustling and then run your own mini company all by yourself.

  • Jane Savers

    I regret not quitting my safe dead end job and moving to my current employer sooner.
    Better pay and benefits and leaving a b*tchy coworker who sucked the joy out of every day should have happened years earlier if I was just not so afraid to take a chance.

    • Mochi & Macarons

      The good news is that you didn’t retire at 65 with those thoughts 🙂 You’re out now, and making the most of it!

      My mom had a similar regret.

  • eemusings

    I have no serious career regrets at this stage (well, except not choosing something that makes money! Unfortunately the things I love and am good at are not lucrative) though I do wish I had networked more when I had the opportunity.

    • Mochi & Macarons

      Maybe now your traveling will help you network. I have friends who found jobs just by chatting with strangers who needed their specific skills.

      Now she lives in NYC and works for them.

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