Career Advice Archives - The Grassy Road

Are you coin operated?

What does it look like when someone is coin operated? This is the person who, any time compensation comes into play, deeply cares how much money they will make. Their focus on their earnings outweighs any other circumstance: what is best for the company, what is best for their own future, how the situation impacts their peers – and they are often oblivious to how it makes their peers see them. And how they view the people around them comes into play too. Yes, sometimes I joke that sales people [...]

By Penny Herscher|2025-03-31T11:11:26-07:00March 27, 2025|Career Advice|Comments Off

The challenge of FOMO in your career

FOMO today is typically about missing out on something cool – someone’s vacation on Instagram, a restaurant they ate at, their new car. Merriam-Webster defines it as “fear of missing out : fear of not being included in something (such as an interesting or enjoyable activity) that others are experiencing”. But in the rat race of our modern careers FOMO happens around your choice of profession too. I see this many times when coaching people at transition points in their careers. You’re working at a large company (in a good [...]

By Penny Herscher|2025-01-24T08:49:08-08:00January 23, 2025|Career Advice|Comments Off

Why Goldman Sachs’ behavior in Bully Market by Jamie Fiore Higgins is just not that unusual

I have just finished reading Bully Market – the story of how Jamie Fiore Higgins rose to MD at Goldman Sachs while hating the culture but loving the money. It’s a fast fun read, not great literature but a compelling insight into the behaviors women have put up with in the last 30 years that are all too common, and yet still egregious enough to be shocking. She’s brave to write so frankly about what she experienced – hats off to her. You can read the NY Times review here. The [...]

By Penny Herscher|2022-11-08T13:29:58-08:00November 7, 2022|Career Advice|Comments Off

Visiting the Luiss Business School in Rome

I was fortunate enough to be asked to speak at the Luiss Business School in October - in Rome no less! The discussion centered on tech, subjects like AI, China, Semiconductors and then the role and importance of diversity. And all within a gorgeous 16th century papal palace. Professor Pierluigi Matera graciously interviewed me in two settings: One on one and then with a group of students. Here are the two videos. My comments on diversity start at ~35:00 in the first one, and thread through the second one. https://www.youtube.com/watch?v=MIpKJWhWDBA [...]

By Penny Herscher|2021-11-05T14:51:11-07:00November 5, 2021|Career Advice|Comments Off

The choice we make to be loyal, or not

Is loyalty a good thing – or is it a dirty word? Depends on the context – politics, business, your family? But when talking about professional loyalty it can be a double-edged sword. Fundamentally to be loyal to another person is a choice you make. You may have several different reasons to choose to be loyal. You may admire the person – their intellect, their effectiveness, their values. You may be grateful to them for helping you through a tough situation. Maybe they made you money, or promoted you and [...]

By Penny Herscher|2021-09-15T05:56:09-07:00September 14, 2021|Career Advice|Comments Off

Men to avoid: the ones who tell you to slow down

There is nothing more demotivating than someone above you in your chain of command telling you to slow down, to be less ambitious. Especially if you are a woman and the teller is a man. This behavior is, of course, not new. So many of our mansplaining experiences are captured in the new book Men to Avoid in Art and Life by Nicole Tersigni - I'm using one of her captioned paintings here to illustrate my message. A laugh-out-loud joy of a book and Twitter meme. I was coaching a [...]

By Penny Herscher|2021-01-28T10:02:30-08:00January 19, 2021|Career Advice|Comments Off

Talk in Powerpoint not in Word!

It's tough to listen when you just want someone to get to the point. People talk too much for many reasons: nerves, wanting to be recognized or heard, wanting to look knowledgable or sometimes even because they enjoy talking, have lots of thoughts in their head and want to get them out. If you are with friends in a restaurant and they enjoy your style - who cares? But in the office talking too much will work against you because you'll suck up other people's time which they will, eventually, [...]

By Penny Herscher|2019-03-07T08:49:00-08:00March 5, 2019|Career Advice|Comments Off

Startup or large corporate – which is best for you?

Everyone has an opinion of whether you should work for big companies or small, startup or corporate, but the answer is very personal. I was coaching a group earlier this week and the question came up as "I am working for a startup but everyone is telling me I should go work for a big corporate now for my resume - what do you think?" I believe there is no right way, no right answer. But there are dimensions to consider as you map out your next step. Are you [...]

By Penny Herscher|2019-01-04T09:57:47-08:00November 16, 2018|Career Advice|Comments Off

So you want to raise money – chose your investor carefully

At least once a week I take a call, or a coffee, with an entrepreneur who wants advice on how to raise money. We talk about her product and market, the stage of her business, how good is her story and what her vision is. And then we talk about the tactics of raising money. How to get a warm intro to reputable investors, how to think about angel vs. seed vs. venture, how much to raise, what a strong pitch looks like - the usual tactical coaching. Yesterday I [...]

By Penny Herscher|2019-01-04T09:59:20-08:00October 27, 2018|Career Advice|Comments Off

There’s no dishonor in being fired (most of the time)

So you "get fired" - what does that really mean? And should you feel bad, or is it an opportunity to review where you really belong. Let's start with the word. Fired. The web has a variety of etymologies for the word fired being applied to losing ones job but the version I grew up with is that when a craftsman was very bad at his job (say... working on a Medieval cathedral) and he was kicked off the crew his tools would be thrown into the fire (so he [...]

By Penny Herscher|2019-01-04T09:59:44-08:00September 7, 2018|Career Advice|Comments Off