Episode 179: Sixtyish and Loving It: Perseverance and the Midlife Career Change

People say, wouldn’t you like to be 30 again or 40? You know, I’m loving being this age...it’s a stage of our lives that can be just as rewarding and achieving as every other stage, if you put your mind to it.
— Heather McGregor
Professor Heather Mcgregor

Professor Heather Mcgregor

In the last couple of episodes we discussed the transitions working couples go through during their lives. In this show we re-meet a former guest who’s half of one such couple. Heather McGregor embraced a big career change at 55, going from entrepreneur to academic dean running Edinburgh Business School. She’s continuing a stage where she's switched from supportive partner to family breadwinner.

This transition involved a big move and, initially, living apart from her spouse and son. It hasn’t always been easy, but, she says - like staying married - it’s been worth it.

Heather has always had an eye on the future, planning for what might come next. She believes it's never too late for a career change, as long as you prepare ahead of time.

You can also read a transcript of the show.

Heather is the author of several books, among them Mrs. Moneypenny’s Career Advice for Ambitious Women.


For many years Heather wrote a column for the Financial Times as Mrs. Moneypenny. I first approached her for an interview in 2012. She’s appeared in these past episodes.

I realized after I put this list together that the last time she and I spoke was actually in 2015, not 2016 as I said in the podcast.

Episode 4: Getting Ahead

Episode 11: Women of a Certain Age

Episode 18: The Power of Image

Episode 26: Get Ahead. No Guilt.

Episode 147: Forced Out

Episode 26: Get ahead. No guilt.

September 23, 2013

"We had never experienced anything we thought to be remotely gender discrimination. So we couldn’t even identify it when we saw it. And this wasn’t blatant discrimination, this was kind of subtle, cultural things you couldn’t really put your finger on." - Jessica Bennett

“I don’t do guilt...it drains you of energy to do anything useful, or to move forward in your life." - Mrs. Moneypenny

Jessica Bennett in New York

Jessica Bennett has already had a career a lot of journalists would envy. She's written for plenty of national publications, worked at Newsweek for seven years, moved on to micro-blogging site Tumblr, and now heads editorial at Sheryl Sandberg's Lean In foundation. She never expected to come across any "gender issues" in her career - as far as she was concerned, that stuff had happened in the past. Everyone was equal now. But the reality of life at a national magazine turned out to be a bit more complicated.

In part two of the show I sit down again with Financial Times columnist Mrs. Moneypenny, otherwise known as Heather McGregor, to talk about quashing female guilt, learning how to say no, and building a reliable support network. 19 minutes. 

Show notes: The article Jessica Bennett and her colleagues published in Newsweek about the 1970 lawsuit, and their own experiences at the magazine, is Are We There Yet? And this is the show where I interview former Newsweek journalist Lynn Povich about her experiences fighting gender discrimination at the magazine in the early 1970s. 

Heather McGregor's book is Mrs. Moneypenny's Career Advice for Ambitious Women.

Also, don't forget the Squarespace sponsorship offer. While we're still in September use the code 'broad 9' to get a 20% discount if you sign up for a site. That's only in September, while supplies last.

TRANSCRIPT:

Welcome to The Broad Experience, the show about women, the workplace and success. I’m Ashley Milne-Tyte.

This time on the show, two perspectives on getting ahead at work. The first comes from a Generation Y journalist who thought she was doing all the right things…only to realize subtle and complicated factors can get in the way of career progress.

Then I talk to a seasoned business owner and Financial Times columnist who has firm views on how to thrive at work – including learning how to say no and getting rid of guilt.

Coming up on The Broad Experience.

Jessica Bennett has already had a career a lot of young journalists would envy. She’s written for many publications over the years, and worked as a writer and editor for Newsweek for seven years before the magazine eventually folded. She then moved on to be executive editor at micro-blogging site Tumblr. Now she’s editorial director at Facebook COO and bestselling author Sheryl Sandberg’s LeanIn.org.

When we met, I told her I’d noticed her own Tumblr site bears the title ‘good girls finish last’. She had to go back a bit to explain how she came to that conclusion.

“I grew up in Seattle which is like this heaven of a place where everyone is equal, we have female governor, I went to public school, I never really thought about gender issues because the women outpaced the men every way imaginable…so went to college, moved to New York, got my first fulltime staff job job at Newsweek, just assumed I’d excel the way I always had… I was one of those typical over-achiever young women. I was at Newsweek for a few years and it just felt like I wasn’t getting credit that I wanted to be getting or getting published as much as I wanted to be published…I started as an intern and worked my way up and along the way I saw a lot of male interns get hired faster than I had. I was a temp for a full year and every 3 months I would have to up my temp time and my ID access card would stop working…and there was a point where for a week I was unemployed before they could bring me on as a temp, again…but while all that was happening men who were my age and equally skilled got hired on staff. So why did I feel I was still on a tryout?”

In addition to all this she says the arrival of a basketball hoop in the newsroom contributed to a bit of a frat boy atmosphere – again, nothing terrible was happening, no one was making sexist comments or openly denigrating anyone’s work, but she couldn’t help feeling things were just – off.

“So I started talking to some friends about this and it turned out everyone felt the same way. All the young women in the office had noticed this. None of it were sure what it was or what to call it, or how to identify it, we were all raised of the generation to think we were equal. We had never experienced anything we thought to be remotely gender discrimination. So we couldn’t even identify it when we saw it. And this wasn’t blatant discrimination, this was kind of subtle, cultural things you couldn’t really put your finger on, but we just had this feeling that something wasn’t quite right.”

Then, Jess and her colleagues made a discovery. They found out that 40 years earlier, a previous cohort of Newsweek women had sued the magazine for gender discrimination. If you’ve been a longtime listener to the show you’ll have heard about this in episode 8 – in that show I talked to journalist Lynn Povich, who was one of those Newsweek women, about how the case changed her and changed things for women in the media.

Inspired by finding out about that case, Jessica and two colleagues ended up writing an article for Newsweek called ‘Are We There Yet?’ in which they talked about that 1970 case but also raised some of the issues they’d been grappling with at work – how much had really changed in 40 years? The piece became quite a talking point in the media, and the women hoped it might drive change at the publication. But the kind of change that came wasn’t quite what they’d been hoping for. Because while all this was going on, the world of journalism was getting ever shakier…

“So ultimately the magazine was put up for sale. It was six months of hell – every day we’d go to work, didn’t know if we’d have jobs the next day. People had whisky under their desks, more so than usual. Ultimately It was announced Tina Brown was taking over, it was really exciting – she’s an icon in magazine journalism, she’s a woman, and so I stayed on, I stayed on for about a year.”

Even though more female bylines appeared under Brown’s leadership, Jessica says the bigger problem was that Newsweek was failing, like plenty of other magazines and newspapers. Newsweek stopped printing in 2012. Jessica moved on to work for Tumblr…but the world of experimental journalism is no more secure than that of traditional journalism. That job ended after a year. Now she’s working at Lean In.

I asked her what she’d learned in her rocky decade or so in the workplace and if she had any tips that might be helpful for other people. She says she’s gone from shy to direct in the course of her career. Still, she often calls up the image of a friend when she really wants to get something done…

“I have this friend Adam, who I shared a wall with at Newsweek for a number of years, he was always one of the most badass editors, and would ask for what he wanted, he could make a case for anything, convince anyone of anything…so sometimes ask myself what would Adam do, when I’m going into a meeting or want to ask for a raise. I literally think what he would do. Because he’s like the direct version of me, the more direct version of me. He of course doesn’t need to worry about being deemed too aggressive…you know, there’s a fine line for women when asking for things. But kind of taking myself out of myself sometimes and thinking what another person would do in my situation I think helps.”

Any other advice?

“I mean as far as journalism these days, I guess my biggest tip is you kind of have to create your own job…there’s just not jobs out there like there used to be…

AM-T: “And then work out how to get paid for it, in my case…”

I was at Newsweek for 7 years, that’s probably the longest I’ll be at any job. It’s like the opposite of my parents’ career trajectory, which is you start jumping around at different jobs and then you find the right one stay there for years. I got in at the end of this golden era of journalism, like the, I was on the sinking ship, I stayed there for 7 years, now it’s pretty much sunk and now you have to just jump around from thing to thing trying to figure out what the next innovation’s going to be, or how you can possibly use these skills and kind of mold them into something else.”

She says journalists shouldn’t be afraid to pitch a job, either. That’s actually what she did with her current job at Lean In. When she interviewed, there was no editorial position. She pitched the idea, they said yes, and gave her the job. Talking of skills, I asked her if she knew how to code, something everyone’s being encouraged to learn these days – she does, to a certain level, and she knows how to do quite a lot with video too…

“That’s from years at Newsweek and just jumping in on different things, and I think identifying early at a place where a lot of people didn’t ever identify this that that was going to be important, and that if I wanted to grow I needed to have well rounded skills. Because nobody just wants a writer any more. They want someone who can do everything.”

Jessica Bennett, currently doing if not everything then most things on the editorial side at Lean In.org. And I should say in the interests of full disclosure that since I interviewed Jessica during the summer Lean In has been posting some of the content from The Broad Experience.

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Next we hear from someone in the UK who’s at a later stage of her career – though she says she expects to work into her seventies. Some of you will remember Heather McGregor from previous shows. She masquerades as Mrs. Moneypenny in her weekly column in the Financial Times. She has her own business, she’s married, she has three sons, and she’s the author of a book called Mrs. Moneypenny’s Career Advice for Ambitious Women.

 Oh, and she has a distinct point of view on what holds women back at work. Take guilt.

 “Yes, I don’t do guilt. All these emotions take up a lot of energy. If you feel guilty about something it can just weigh over you like a cloud, eats at your self-confidence, you feel terrible all the time. That drains you of energy to do anything useful, or to move forward in your life. If you’ve done something you regret. If not possible to say sorry, just put it behind you and move on. Everybody makes mistakes.”

Now my guest on the last show, Jodi Detjen, has strong feelings about guilt too and I think she’s right to say that guilt comes when women think we’re breaking a rule. We feel guilty because we’ve internalized the assumption that we SHOULD be nice to everyone all the time, or we SHOULD be spending all our time with our children – so one of the ways to ditch guilt is to question those age-old assumptions that underlie your thinking about your role as a female. Heather McGregor says there are various types of guilt women tend to get hung up on. One of the most common is guilt at saying no to a request.

“You are asked to make the cake sale for something, or you’re asked to do something, to make a charity gala dinner, asked to give someone one-on-one careers advice. First, acknowledge that you can’t be everywhere. You will just be average at everything…no one will get proper attention. So I’ve just come from an email from a pretty famous TV presenter in this country, who’s a woman, asking for one-on-one advice having read my book…non-executive director position…she wants my personal advice. This is an hour of my time, I will not be able to charge for it. I can’t do anything to specifically assist her because I don’t run a search company that does board positions and I don’t influence chairmen. I encourage and support women but I don’t make any difference as to whether they succeed or not. All she will hear is what’s in book all over again. I’ve written back to her and said I won’t see her. But in writing back and saying I won’t see her, I’ve written three suggestions of things you can do to help herself, so when you say no to something, I can’t make the bake sale but here’s what I’ll do, I’ll donate $15 towards the cake ingredients. Try and say no in a positive fashion. It’ll make you feel a lot less guilty.”

But there have been occasions when she’s fallen into the guilt trap. She’d been writing her FT column, which often deals with being a fulltime working mother, for about a year, when she got a warning note from a reader…

“My oldest son at the time, he’s now 23, so he was only about 12 years old. The reader wrote in and said I used to be like you…I used to put my career first, but then my son had a nervous breakdown, and I realized it was all my fault…so she said you’ll end up like me with a son with a nervous breakdown. I rang my son, who was on school break, midterm break, I knew where he was, he was with my sister and they were going to the cinema. I rang my sister on her cell phone…and spoke to my son and I said to him where was he, he said in the cinema foyer, and I said I would come immediately to the cinema and join them for the show. And he said, why? And I said, I’ve had a reader write in and say if I don’t spend more time with you, you’ll have a nervous breakdown. And he said, ‘Mum, if you come to the cinema right now I will have a nervous breakdown.’ You know, it’s not what he’s used to, he’s not used to me coming to the cinema in the middle of the afternoon, he thought he was having a perfectly nice afternoon with his aunt. And that is what his expectations were managed to. So I think it’s all about what you manage your expectations to.”

Heather does a lot of expectation managing with her family. But she’s always open, she says, about the reason why she can’t do something or be somewhere, which helps keep everyone on the same page.

“So I believe in that full explanation. Actually, particularly the concept of opportunity cost. So every time you say yes to something you are saying no to something else. So saying yes to everything is only going to get you into hot water. You are going to end up not doing the things that matter if you’re not careful.”

AM-T: “And this is where people get so spent, because in general women do say yes to too much…”

"Yes. And then eventually what’ll happen in they will all just collapse in a heap and nobody is any better off. And then people say it’s very selfish to think of myself, I should be thinking of my children, I should be doing all these things for everybody all night long. And actually, no, you should be looking after yourself.  If that sounds selfish think of this: when we are all on airplanes and they go through the emergency drill, they say in the event of emergency oxygen will fall from the box above you. And why do they say that? They say in the first instance put on your own oxygen and then turn to help the person next to you, even if that’s your child, because if you are healthy and breathing and OK you are going to be in a much better place to help the minor person or the child next to you. So if your career is going well, if you are doing well, able to provide for your family, your family will be better off.”

Talking of family…she’s hardly the first female professional to have been criticized for not being at home enough…

“The truth is, parenting is an individual decision…some people want to stay at home and will stay at home, and that is their choice and I really respect it. I personally would struggle with that, but that’s a very personal decision. But I see far too many women who make that ultimate sacrifice and then 20 years later are in my office saying, ‘Oh my goodness, my children have left home, I have no qualifications and no relevant work experience…my husband may or not have left as well, and I’m now on my own and I have no way of earning a living.’ Well, you’ve had 20 years to plan for that, I’ve got no sympathy.”

To make it easier to work and parent at the same time she insists women need to ask for help and build up a group of people around them who are always willing to chip in in an emergency. I told her about one of my friends and listeners who lives in Westchester County, New York. She told me she’s started trying to create the kind of community she wants – offering to babysit someone’s kid if she knows the mother – and it usually is the mother – is very busy. She says she’s doing this because she wants that same network to be there for her when she needs it. She feels few women do this kind of thing anymore. We’re too busy trying to do everything on our own.

“Well she’s absolutely bang on the money, whoever you are in Westchester county, keep going, that’s exactly what you need to do. If you are not helping other people, you are not building a team.  You’re not building a sustainable community around you – you need to help other people. You may never need to call back in the favor, but that doesn’t matter. And the favor may not be the same thing, i.e. you may watch someone else’s children, but you may not have any children of your own, or your children may be older so you may never need anyone to watch your children. But you know what, at some point you may need to go away for three days unexpectedly and need someone to feed the cat.”

So she says always help out without necessarily expecting a return, but see it as building a network you can rely on when your job threatens to mess up your life.

That’s the Broad Experience for this time.

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I’m Ashley Milne-Tyte. Thanks for listening.