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My biggest career mistake

I posted this on Instagram a while back:

The responses I got were on both sides of the coin.

Some agreed, others disagreed saying it was a privilege of being rich to be able to say whatever you wanted, so I wanted to unpack these responses in detail.

Rich is relative

Even if we are just talking about money here, not what “rich” means (e.g. rich in community, friends, social connections, etc), being “rich” is relative to those around you.

I am rich compared to averages of people my age, and taking the crazy high achiever millennial net worth (and not the average millennial one) I am about 2 years younger than the oldest millennial with triple that average net worth, which makes me…. “rich”.

(Feels weird saying I am even a millennial, as I picture them all as young 20-something year old whippersnappers)

I feel rich relative to others my age for sure, but I am definitely not rich compared to people who live in my neighbourhood. These are people who have Ferraris, Rolls Royces (they get a new one yearly it seems), massive 3000 square foot mansions with indoor pools (!!) and sending their children to $25K/year private schools (definitely not me).

I am “poor” compared to them, but it is all relative.

In the same vein, I know people who have all of that above, and feel POOR compared to others because their colleagues/neighbours have EVEN MORE than that (think: tens of hundreds of millions).

Inversely, I also know people who have less than what I do saved, but feel extremely rich because it has been a major upgrade from what they used to have saved, and don’t need much anyway, so they’re happy.

And ALL OF US are rich AF compared to the poorest in the world who live on pennies a day.

So, “rich”? Relative to those around you – family, friends, neighbours, and colleagues.

Being Rich versus Rich Mindset

You can be rich with a poor mindset

My parents won the lottery but then wasted most of it. They were “rich” for a time being. Life was flush with Rolex watches, Mercedes-Benz cars, a fully paid home and my parents not working at all (well my mother went back to university to re-educate, but my father just worked part-time at some minimum wage job.)

They were rich with a poor mindset.

This is not uncommon for lottery winners. When you come into a lot of money, the advice most professionals give is to sit on it for a year. Don’t make any purchases. Put it in a bank account, sit on it, think about it for a year, and then act.

A lot of lottery winners (we know indirectly of another one), blow their entire fortune (doesn’t matter how much it is) and are back to where they were before or worse, before the year is up, more or less.

…and you can be poor with a rich mindset

You can be poor with a rich mindset (e.g. my mother when she was clawing her way out of a poor village to be somebody)

I am talking about mindsets, not whether you have money or not.

You are going to find at any income and social level, people who are the salt of the earth and kind, sweet, generous folks, and at the same level, people who are complete a**holes.

Don’t take one person as an example for what to do for everyone

Remember, this is a general SURVEY, and it is never black and white, like “all rich mindsets never blurt their minds out any time they want” — only 6% of the rich mindsets blurted their minds out and spoke their truth, and 31% of the poor mindsets held their tongues!

You are going to find everything at every level, but the GENERAL TREND is that those with a rich mindset do not speak their minds.

Of course there are rich people who run their mouth and do well. But they are not the majority, nor the role model for the rest of us. In fact, they’re probably the worst role models to follow because they may seem to “get stuff done” by screaming their heads off and always saying what they feel on Twitter, but at what cost?

Consider that looking at one person to generalize to everyone (and to yourself) as an example of what to do, is a dangerous slope.

You aren’t them and you aren’t in their position nor with their power.

Are people going to react to you in the same way they would react to them even if you said THE EXACT SAME THING?


Once you are where they are, you’ll be that outspoken person who starts up riots and says exactly what they mean, but until then, you need to consider more tempered advice until you can reach that position to be in that 6% who do speak whatever comes through their brain.

There are BIG difference between honesty and complaining

I am pretty outspoken. I speak my mind, and I am not shy about it (clearly).

A huge mistake I made in my career early on, was thinking that EVERYONE wanted to hear the truth.

The truth about how crappy this project was, how incompetent that manager was, what we were doing wrong, etc.

NONE OF THAT is helpful. That is not helpful “speaking your mind” business, because I was just complaining/whining.

Yes, complaining is being honest, but it isn’t a constructive sort of honesty people can take and use.

Rich mindsets offer solutions

I had offered zero solutions to the situation, and it wasn’t helpful at all to management, it was stressful and bothersome to have such a negative voice on the project.

I see that now in hindsight, but during the time I was there, I mistakenly believed I was helping because I was being honest. I wasn’t pretending things were rosy (they were not), but I also wasn’t helping.

When you have a rich mindset, you complain but you offer a solution to the situation.

Example: We are unable to efficiently pack and ship these packages quickly and customers keep calling and screaming because we are missing deadlines and/or paying fees

Poor Mindset Complaining: This job sucks. We’re unable to get the packages out because it takes so long but then we get yelled at by customers. I hate this job. I don’t get paid enough.

Rich Mindset Solutioning: Why don’t we get more helpers? If we cannot afford that, let’s organize the space to make it more efficient in these ways, like placing all the tape and scissors in one spot, the empty boxes in another area, more tables, and maybe break down the tasks so that it is not one person doing the whole process, but a Henry Ford style break down of tasks?

Rich mindsets speak their mind when it is worth it to do so

I also never knew when to keep my mouth shut. I said any damn thing that came into my mind, and subsequently did not get extended as a result. Surprise, surprise. /sarcasm

I didn’t learn to pick my battles. I fought over EVERYTHING because I was a know-it-all, and even when I was proven to be right, it was at what cost?

My reputation as basically being feisty was not a good one because I fought about everything, so no one could tell what was really a big important fight, and what was a minor one.

Choose your battles wisely. Is it going to help you? Hinder you? Set you back years in career development?

Is it worth fighting for? Is it something in your area you have to control with and will reflect badly on you?

These are all questions worth asking before taking a stance against a bunch of people or upper management (all of which I have done).

My other poor mindset with “speaking my mind” any time I wanted, was I kept hammering my same points home, over and over again, even if they weren’t well-received.

I figured if I just kept saying it, repeating it, and getting louder and louder, it would eventually turn my way (not at all what happened.)

Sometimes you just have to let it go. Even if the decision seems wrong to you, and you’ve already said your piece, leave it be. At least you said something.

Just don’t be aggressively forceful about it even though you know you are right. Sometimes, like with children, they have to learn it on their own.

Rich mindsets are diplomatic and tactful

Even if you have decided to battle it out, you’ve decided it is worth it, it will not damage your career beyond repair if you do end up being wrong (or whatever), and you really feel like this is the right direction to go in, there are various ways of saying it.

Like with talking to children, you have to know how to phrase it.

Example: This project deadline of 5 months is crazy.

(This is a real life example of me. I was a Poor Mindset consultant at the time.)

Poor Mindset Speaking: This deadline is insane. It is ridiculous. How can they expect us to make it? We can’t even do X, Y and Z and then it is on top of each other, everything is a waterfall effect. I hate this project, I hate the way they end up deciding these things without even considering what it takes to deliver. They don’t know what they’re doing and they’re clueless at upper management. How are we going to get everything done? I can’t do it all!

Rich Mindset Speaking: The deadline of 5 months is very tight to deliver a full project to completion that normally takes a year. Do we really need to deliver in 5 months? Have we asked the question of “what if” we push it for even 3 more months, what will this do? What if we are late? What’s the consequence? Is there a contingency plan in place?

What are the risks? Are we able to perhaps cut out certain tasks we would normally do on a full-scale project, and scale it down to what is reasonable and realistic in 5 months?

Have we maybe looked at pushing certain tasks for until after the project is completed like documenting processes, rather than going through the formal channels of documenting everything beforehand? Where can we save time?


The message was exactly the same, the delivery wasn’t.

My delivery sucked. I was dismissive, rude, angry, stressed, and none of that of what I said was helpful. THEY ALL KNEW THAT ALREADY.

What I should have said as my second Rich Mindset, was to push it back onto them to say: I agree with your (insane) 5 month deadline premise. How will we make it? Let’s solution this out.

The difference is my old poor mindset was focused on MYSELF. How I was going to squeeze a 1-year project worth of work into 5 months, and how I was going to be impacted with the stress of what was going on.

I didn’t solution it out — I didn’t focus on the project itself with its hard deadline of 5 months (for accounting/fiscal year reasons apparently), and then roll up my sleeves and offer what I could do in that timeframe. I was sure that 5 months would not be doable to squeeze in 12 months worth of work, but if I eliminated 3 months of work with process documentation and all the stuff upper management liked, and did it AFTER the project was over, while still hitting the deadline, I may have been able to do the same in other areas.

If at the end, they realized that even cutting out all of these tasks would STILL not deliver the project on time, perhaps they could have taken that to upper management and gotten more time. Who knows?

All I know is I never asked the right questions.

Rich mindsets understand all the micro work cultures

This was also a big one for me. I hate being managed. Actually, I hate being micro-managed, asked about my time, having people over my shoulder asking and checking. It drives me insane.

As a result, I didn’t have much, if any, respect for upper management. I saw them all as pencil pushers (and to be fair, a lot of them are, I still work with many who are like this today), but it wasn’t fair to paint them all with the same brush.

I used to take this mindset to every client, no matter what and without taking the time to understand the management, adjust my approach and be aware of the political games that are TOTALLY HAPPENING whether you participate or not, I was getting screwed.

Sometimes, one manager can be really into face time. As in, you’re in the office 5 days a week, 8 a.m. to 5 p.m., and if your bum is in the chair, they’re happy. You have to understand as an external consultant what that looks like, and show up accordingly if you want to appease that manager.

Other managers, don’t care about that at all. They care about you delivering results (they’re my favourite kind). You could be in Timbuktu for all they care, but you better deliver.

You have to understand the work culture you are at, and what makes them tick before speaking up about things. If you are going against that grain to try and change their mindsets, then go into it with your eyes wide open, understanding that you’re a square peg trying to fit into a round hole.

When you don’t understand any of that, you open your mouth and put your foot into it, saying to the manager who LOVES face time “I don’t get why people are so into seeing me in the office when I do the same work at home! That’s so dumb, expecting people to be there all the time.

Umm.. awkward.

Understand what your manager actually cares about & phrase it in their way

They say the right things they’re supposed to, but you can tell they don’t believe in what they are saying.

Don’t pretend or bother joining in then, if you know this.

The C-level executives can say all sorts of platitudes and all of the “work rah rah” speeches that they want but at the end of the day, you’re not working for a C-level executive (most likely), you’re working for a manager. That manager has to believe in that speech, and it is up to THEIR manager and all the way up the chain, to demonstrate and show that they do mean what they say.

It takes time. People don’t change over night, and maybe managers need to be replaced.

In the meantime, just be aware of the situation. Try, but don’t insist.

If your manager only cares about the budget, then phrase things in that way. If you need more time for a project, you tell them: I need X amount more of money for this project to complete it properly because of these reasons. Alternatively, if we do not get this amount of money to extend the project to do it properly, these are the consequences and risks. What do you think?

You have to know how to say things in a way people care.

Rich mindsets understand office politics and temper their words

Everyone knows there is politics in a company. You have to know who is thinking what, at your level, your manager’s level, and above them.

Understand who they are as managers, and act accordingly. I can’t advise past this point because I don’t know your work cultures, but an example would be if you know there are 3 competing managers who are all vying for a position, and are getting aggressive with their deliverables.

Instead of complaining about it, and wondering if you should leave, perhaps even pushing back and getting angry at your manager, why not consider another approach?

Maybe they’re new, and trying to prove themselves, and using their team to prove how awesome they are from the get go, stemming from their insecurity, or even lack of knowledge of the company’s processes.

For the manager who is new, eager to prove themselves and probably insecure at their new position, why not treat them as such?

Offer up tactful tidbits like: We normally have to complete task A before B because of the approvals that are required. It takes less time if we do it this way, rather than the way we might normally think (e.g. the way they are suggesting), because of X reasons.

Maybe they’re hands-off, somewhat lazy managers who think they shouldn’t do any of their tasks and you should do it for them, but also your job on top of it.

Try saying: I’d be happy to take on Project A for you. What should I eliminate from my workload to get this completed? Here is what I am currently working on, please let me know what the priority is.

Maybe they’re micromanagers because they’re unable to let go of their old job even though they’ve been promoted and you’re doing their old job, and are feeling like they want to do BOTH jobs, but in the end, are undermining you.

You could say: I understand you’re transitioning to a new role, and I appreciate all of the help and involvement you have given to me and shown thus far. I’d like to make your transition easier to your new role, as I am sure you have lots of new duties and responsibilities.

Instead of you coming to every meeting and being on every email chain, why don’t I create a spreadsheet with all of the various projects that are going on, and give you a weekly, or even daily 15-minute status so that you’re still in the loop but not in the details? You can leave that to me, and then offer your advice during our daily stand-ups. What do you think?

Speak a version of your mind when it is beneficial

Think about the battles you’re fighting. Are they worth it?

There are plenty of ways to get what you want, and to get the message you want across.

You just don’t need to always speak your mind 100% without a filter. This is fine when you’re a child, but as you get older, there are other things to consider if you want to navigate through the corporate world.

You can speak a version of your mind when it helps you, the company, and/or your manager, in a diplomatic manner. Say your piece (or not at all) and let it go.

The best managers are tactful, diplomatic, kind, fair, and able to get their messages across in a clear manner.

Not all managers are great, but you’ll certainly go farther with honey than with vinegar.


  • Middle class

    Wish I read this 3 years ago! I think it might be too late with my boss but I will try to be more diplomatic and offer solutions even if s/he is horrible at prioritizing, micromanages, has unreasonable deadlines and is not so tactful him/herself.

    I really love my field and the company but at the end of the day, your immediate boss has the most impact.

    Anyway this ia great advice that I try to remember at my next job!

  • Catherine

    This. Is. Amazing.

    It’s so true.

    If I can be so bold to try and summarize your amazing post – is that being in a rich mindset for holding your tongue involves:
    1. Be self-aware of your surroundings and how your words/actions impact others
    2. Be “client”- focused. Focus on not what you want to say, but what your “client” wants/needs to hear, and the “language” they speak.
    3. When you do 1. and 2. it’s a lot easier to be solution-focused

    Note: The “client” can be anyone who is your audience, whether it’s your manager, your staff/employees, an investor or upper management.

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