The Startup
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The Startup

I let my job take this away from me. Don’t let it happen to you.

Photo by Patrick Schöpflin on Unsplash

Looking back over 8 years of what has been a successful career in one of the largest corporations in the world, I can’t help but think back to one of the first meetings I had at the company a couple of days after joining from business school.

Somebody just got fired. And not just anybody in fact, but one of the most senior managers in the office.

The head of the department got everyone into a large conference room and after dropping the bombshell that this senior manager wasn’t coming back, he went around the conference table and asked everyone how they were feeling and if we had any questions.

Everyone had cookie cutter responses about how they were surprised, but they were ready to do what had to be done to step up and fill the gap, blah blah blah…

Except when it came to be my turn, I had a question:

What is the lesson that we should all take away from this?

I got a pretty short answer that I wasn’t really satisfied with but that was pretty much that. It wasn’t until later in the day that one of my co-workers tipped me off that I had said something “wrong”. Something along the lines of:

How could you ask something like that in there? Not really a great way to make a first impression…

I was immediately taken aback and horrified that I had done something that could torpedo my career only a week after it had actually gotten started. After this, I started to examine everything that came out of my mouth, to be sure it would not be something that would put me in a similar situation.

Over time, I came across many situations like this, where if I said the wrong thing I was gently reminded by a co-worker or not so gently reminded by my boss, that I should not be trying to put them on the spot or make them look bad in front of everyone else.

And you know what happened? Over the years, I was trained to either say the right thing or not say anything at all. Not only that, before long I was getting nervous to speak with people just because they were 1 or 2 levels above my boss, because of the pressure to avoid making the wrong impression.

What was really lost

I’ll be honest, doing this was beneficial for my career and I was rewarded for taking this kind of approach. I built a strong reputation inside of the company, I was promoted a few times and in general didn’t make too many waves.

But the more that I think about it I should have done better, because just getting by isn’t good enough anymore.

Having the courage to ask tough questions may be one of the the most important skills that you can have now. Think about a company like Facebook where there are legitimate questions about whether the company is going in a direction that is beneficial for society or not.

Sitting back and not making any waves just isn’t good enough.

You have to make sure that your voice is heard in determining the direction the company is going. The same goes for car companies that are cheating emissions tests or banks that are rigging benchmark rates, or anything else.

And it doesn’t have to be something scandalous either. Think of companies that just didn’t keep up with the pace of innovation, like Xerox, Kodak, or countless others.

These companies actually had groundbreaking ideas inside of their organisation — think of the mouse and graphical user interface that Apple took from Xerox, or the extensive research that Kodak had done on digital photography.

But great ideas need all of the support they can get in big companies like these. There are so many entrenched managers who don’t see it in their interests to embrace new ideas. And by sitting back and being quiet, these new ideas are being killed.

Not speaking up will come back to bite you personally in the long run. It may make things easier on a day to day basis and boost you early in your career, but it is a recipe for complacency and exploitation.

You need to step up for yourself and have a few difficult conversations about your career and how much pay you deserve, otherwise you will never have it offered to you.

Most big companies manage salary increases very reactively, for example, only giving raises when someone has an offer to leave and go somewhere else.

If you sit back for too long, you will undoubtedly be making far less than you should be.

Never stop challenging

Looking back, it is tough to know exactly when I lost that spirit to challenge that I had at the start of my career, but I have a good idea of what the causes were.

I started my career with a mountain of student loan debt and we were in the middle of the worst years of the financial crisis. I did not feel like I could afford to not have this job.

Try not to ever be in this position.

Live as minimal as possible to pay off any debt and maximize your savings as soon as possible. Spend every free minute you can building a startup or side hustle. Not only will this give you the comfort of having a fall back plan, it will take away the fear from speaking up at your day job.

But more importantly I think is this: when I was just starting my job, I had just come from one of the top business schools in the world where every day we were discussing strategic issues, asking difficult questions to guest speakers, and presenting recommendations for companies the same size or larger than the one I was working for.

Doing this made me feel that not only were my questions relevant, but they were important and I had the right to ask them. It was only over time and distance from this experience that I began to gradually lose this feeling.

Don’t be afraid to think about the big picture. Never say, that is above my pay-grade to figure that out. You can and you should have a view on where the company is going and whether or not you think that direction is the right one.

And if it is not a direction you agree with, speak up.

It’s not easy, and I am just building the courage back up to do this myself, but it is the right thing for you to do. And it is only with our combined voices that our companies will do the right thing and the best ideas will win out.

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Greg Dickens

Greg Dickens


Maker, recovering banker, living in Greece. Building affordable digital tools for local news and other indie publishers at