It has been just over seven years since I started working in the corporate world. Seven whole years! And in this time, I have been blessed to have very supportive and encouraging mentors. From a confused student to a working mom, and wife, I have changed as a person. And, as I climb further up the ladder and add more experience to my CV, I cannot help but wonder just where I would be now if I didn’t have a good boss.
We see many people hopping from one company to the next in pursuit of either fulfilment or a nice salary. But one question that has played on my mind is what actually makes everyone else stay. Is it the money? Is it the corporate culture? Or is it the career prospects that one can look forward to?
While I cannot answer this question for the masses, I have been able to identify what that ‘it’ factor is for me. I won’t share everything, but here is the general overview of what I value in a job.

My corporate background
My first job was an accident. And no, I didn’t accidentally apply to the wrong company. I actually applied indirectly without intending on applying for the job.
Ok, let’s take a step back for this to make sense.
As a fourth-year student in university, I spent the year working part-time and enjoying life. It was only possible because I completed all of my credits by the third year. My intention was to spend a year as an exchange student, but plans changed. So instead, I worked hard and played harder.
As a fourth-year student in university, I spent the year working part-time and enjoying life. Initially I intended on spending a year as an exchange student, so I finished all of my credits by third year. Unfortunately, plans changed, so I did what I could – enjoy a gap year before having to worry about a real job.
When graduation started approaching, I decided to apply for a Master’s degree since I could hadn’t really decided on which career path to take. I know, I know, further studies when I hadn’t even decided on a field… Don’t question my choices, it made sense back then!
One fine day, I attended a conference that my dad was hosting since my calendar was free. And during a short interval, the CEO of an international company struck a conversation with me by the coffee station. By the end of the ten-minute conversation, I had secured a job and had his business card nestled in my purse!
So yes, it was a complete accident on my part, but we’ll call it fate for now. I had no idea that one simple cup of coffee would change my life forever.
And let me tell you, God has an interesting sense of humour. I was excited to be starting a role in the marketing only to find out that I was placed in the finance department!
So now that you know where I came from, let’s dive into what makes me value a good boss over a big salary.
A good boss will focus on your career progression
Seven years after the coffee encounter, I am no longer in finance. In fact, that portion of my career lasted only eighteen months before I realised that it wasn’t for me. And just as should be expected from me, I landed my second (and current) job accidentally as well.
If you ask me where I see myself professionally in ten years, my honest truth is that I don’t know. I have a general idea of what I would like to be doing, but my entry into the corporate world has proven that flexibility is a key component of my growth.
Of course, this doesn’t work for everyone, and I’m sure most people prefer having a clear path. But I just haven’t had that epiphany yet. And yet, with a good boss, and mentor, I have steadily climbed up the ladder and earned respect.
Money will buy you shiny things, but there are more things that go into a successful career. Of course, no one would want to work in a place that doesn’t offer growth opportunities. But what good is working in a place where you may or may not have the opportunities but no one to guide you?
Related: How to stop being invisible at work
Learning opportunities
Having someone who makes every aspect of your job a learning opportunity is the key to setting a proper foundation.
I’ve learned that every task is important to the bigger picture. But it isn’t something that I found out on my own. A good boss will make sure that you are constantly learning – be it through experience or by taking courses. A good boss will also make you understand that the simplest tasks contribute to the bigger picture.
When it comes to choosing a job that pays a higher salary or working for a boss that has my best interests at heart, I choose the boss every time. And as a millennial who has big dreams of owning several properties and traveling the world, it is crazy to think that money isn’t top of my list. It wasn’t always this way. Having a good boss has helped me see things through a new lens.
A good boss will get you paid… and then some
The thing about a boss that genuinely cares about you is that they will also make sure that you are compensated for the work you do. I’ve been lucky enough to have two managers that cared enough about me as a person that they even knew my family members by name. They were also invested enough to care about my personal ambitions and support my growth.
When I needed to make a down payment on a lifelong dream, that bonus number surpassed my expectations. When I needed to move countries to be with my husband, my boss overrode a hiring freeze and made it happen.
Related: I will not apologize for being a working mom
And if you don’t have a good boss…
… move – you’re not a tree!
Even though I have been extremely lucky to work under great management, I know it isn’t always going to be the case. So if that is you and you are struggling, know that there are good people out there. You don’t have to stay in the same place working under someone who won’t help you grow.
We spend ten hours a day on average in the office, so it needs to be an enjoyable experience. If that isn’t the case for you, go and find yourself a good boss.
As a person who is starting to build a career, this post is super useful! It’s hard to know what to look out for in workplaces when you’re a newbie, so your experience is super invalueable.
Right now I’m working from home and I never even met my boss. I can’t contact her via phone, and I was switched managers without any notice whatsoever. This type of administrative work feels very disconnected but I don’t mind working from the comfort of my home. I take short cat naps on days where I’m really struggling to stay awake. As long as the work gets done, they don’t care. I do contact tracing for COVID-19 which feels more like volunteer work tbh, and it gives me purpose.
Then there’s the hospital job which is also fulfilling for me, because again, helping people feels more rewarding than a paycheck. I enjoy being on my feet but can’t pick up shifts these days (I can barely walk due to pain)…. hospital work is fast-paced and the artificial lighting keeps me awake. The staff is friendly which makes the work experience as a new grad bearable, despite the stressful environment. There’s pros and cons to different types of jobs. I’m happiest in health care and happy I switched over from retail and the food industry…. I wish I had switched over years ago.
It’s hard to know what we want until we have sampled a bit of everything job-wise. I’ve worked 9+ jobs since I was 16, including a factory job which was surprisingly fun (for the most part). Experience is important, but I lacked a lot experience. My jobs were short lived because I also spent 9 years in university. My sad-looking resume was not going to get me a job, so I included a cover letter as well! I believe that the cover letter(s) helped me highlight my strengths and abilities much better than a resume ever could.
Wow 9 jobs! That’s incredible!
It’s really hard to start a new job without having any interaction with your team or manager, but the fact that you’ve pulled it off speaks heaps about you. It’s also interesting to see that you love jobs that help people. Most of us are in it for the money 🙈
Once baby comes, will you take a year off or will you start working part time?
Once the baby comes, I’m not taking any time off. Right now I’m doing full-time work-from home during the months of May and June 5-6 days/week, and I plan to return to my other job at the hospital in July.
The ironic thing about all of this is that money is abundant right now. I don’t need to do this but I choose to because it gives me purpose. The pay is bonus. If I was only doing this for the money, I would be miserable.
As for the 9 jobs, none of them lasted too long. The one that lasted the longest was a 7-month factory job. Some say that it’s bad jumping from one thing to the next, but my focus was school. I didn’t plan to be in university for 9 years! I think that trying to juggle school and work is the biggest challenge of them all! 🙊
Take your 7 years and add 30 and you’ll find me! Good bosses. Bad bosses. Supportive bosses. Tyrant bosses. Credit-hogging-lowlife bosses. I’ve had them all.
You can’t measure the value of a great boss. 2020 was one of the worst, most stressful years of my career but I survived and I’m still there. Why? I have a great, supportive boss who has my back and I can trust. I know I can be brutally honest with him and there will be no judgment or repercussions. He’s a rare gem.
The only piece of advice I’d give is don’t take a job JUST because of the boss. People come and go. But, if you have the opportunity for a great job and a great boss, grab it!
Wow these things will definitely help , newbies like me in future…
Wonder what a “cup of coffee ” can do🙂🙂🙂
Indeed!! I’m looking forward to reading your throwback years from now 😊
Wise words Michelle! I always love your perspective because you know so much more. 37 years is such a long time! I hope you’ll be sharing some work-life lessons on your blog soon *hint hint* 😉
Ha ha. I actually wrote a whole series on work and career last spring and summer. You can find them on my site under Life Hacks / Work
I’m so happy for you that you have a great boss! I do as well and it is such a blessing. I have learned that the only reason I work is because I need the money. I haven’t figured out how to monetize the things I am truly passionate about, so regardless of who the boss is, it is about the salary for me. The higher it is, the sooner I can be done with the corporate world and give my life fully to the things and people I truly love.
That’s a fair point, and with a family comes responsibility. I hope that one day you’ll be able to just do what you love!
I agree with people leaving if they don’t like their boss and it’s creating a negative atmosphere. At my work, I hear people complaining about the job all the time. All I can think is, “if you hate it so bad, do something about it!” I personally love my job, and think some people will complain no matter what.
Hahah I’m that person
Haha I totally get you but sometimes it’s not that easy to leave – especially with the economy the way it is now. I’m glad you love your job! Or is it jobs?
I wouldn’t expect anyone to go job searching right now (especially in aviation). But I’ve been listening to people complain for years and not do anything. Right now I’m only doing the blogging surprisingly 😄. Surgery means I’ll be off for another couple months.
This is really incredible advice Shelly! I miss reading your content… LoL
Ahhh Ero! Where have you been hiding?!
Hahaha! I’m taking things slow and steady on WordPress this year… been through a lot. I need the break, but I’ll be showing up once in a while.
Thanks Shelly.
Thanks for sharing, Shelly. “Move – you’re not a tree!” is the perfect statement for this situation. There is no doubt that for me, that a supportive and thoughtful boss (when I came across them) made all the difference in the world. Then one day, I became the big kahuna and from there reflected on all the bad things I had experienced under bad/cranky/political/narcissistic/under developed CEOs, executives, managers etc and made sure I wasn’t like they were, although I did have my bad days from time to time. Seeing people who worked with me succeed was (and is) very important to me. These days, I do my own thing work wise and try and help others at all levels be better at what they do.
Gosh Sean I really wish I could’ve had the opportunity to work with you. Every time you talk about your people, they seem more like family or kids. That’s definitely the kind of spirit that a CEO has to have 🙂
Thank you, Shelly. I think we would have worked well together 😊
A good boss is SO important. They’ll support you and help you find what’s right for you, even if it’s not a job under them. I fully believe and understand that good workers leave good jobs because of a bad or uncaring boss.
Agreed! It’s sad to say but sometimes one wrong move can definitely cost a company talent.
Great post! I thought about this a lot when I decided to move on from my 7 year job (that was about 5 years ago)… I’m someone who fears change and I felt very comfortable at that job and had worked my way up in salary and title so it felt like a waste to just walk away. But I knew the passion in my spirit had left and i had absolutely nothing more to give.. I left not really knowing what I wanted to do, I just knew I wanted to help ppl or be in a field where I could feel like I was contributing to society in someway.. I love my job now but I didn’t get here right after quitting.. It took about 2 years.. So to answer your question.. I definitely value good bosses over hefty salaries (I would go as far as saying work culture over hefty salaries) but I think there’s also a certain amount of privilege to be able to say that… Some ppl just don’t have that ability to choose.. So I’m grateful just to be at a job that I love and can see myself at for a very very long time 😊
Gosh you’re right~ work culture trumps salary every time for me too. I get that life isn’t cheap, but the value we put on our mental health has to count for something!
2 years without a job… wow! How did you make it?
Sorry, I meant I was at other jobs for the 2 year gap.. I left one job to hopefully find work doing meaningful work but I didn’t get that job right away so had to work another job that made me question leaving the first job and if I’d ever find that meaningful one… It was a hard 2 years but I wouldn’t trade it! Built character and made me appreciate work culture for sure!