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:
DON’T JUST LOOK AT THE INCOME
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?
BEING YOUR OWN BOSS IS NOT ALWAYS THE ANSWER
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:
- Had no idea how to create a budget and stick to it
- Had no savings & spent every penny they earned & when the famine hit, they starved into debt
- Preferred a stable career with a manager, a structure, colleagues and the whole 9 yards
- Didn’t want to be a Lone Wolf (many freelancers are fiercely independent Lone Wolves…a hard life)
NEVER SAY NEVER
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.


