This article is part 6 of our “Women in the workplace” collection. In February, I had the opportunity to interview professional women from different races, backgrounds, ages, countries, experiences and industries.
We spoke candidly about our challenges, frustrations, failures and successes - and how they can help you on your career journey.
We made the editorial decision to anonymize each woman so that they didn’t have to worry about self-editing. (For an in-depth look at that process, check out this article.) This helped us bring you the rawest response to each question. Each article is focused around a theme: you can read it as a stand alone or as part of the collection.
A career with no struggles. No obstacles to overcome. No difficulties that make you to order a triple cheeseburger at 3am because you can’t sleep. Again.
Nope. I can’t imagine it either.
Because while the hard times* are far from my favorite part of being an adult, challenges help us grow. I can link every bold leap forward in my career to pushing through - usually kicking and screaming - to an obstacle that felt improbably hard.
That’s why I felt that no collection on experiences about the workplace could be complete without this question:
What would you say your biggest obstacles and challenges to date are?
Followed promptly by:
How did you handle it?
By sharing our challenges - and our solutions to them - maybe we can make getting through the muck a little easier for others. And if not easier, then maybe it can serve as a reminder that times will get hard, but you will be through them.
Your first few years in the workplace come with their own set of unique curve balls.
You’re still paying your dues. Still figuring out how to make enough to cover the bills, how to ask for that promotion, how to get people to support your ideas. These early foundations are crucial - but laying them down ain’t easy.
Some careers - especially the early rungs - have appalling starting pay. Almost everyone trying to break into journalism, fashion or the creative fields like acting, music and art has experienced it first hand.
L.’s first job out of college - working as a journalist for a local paper - didn’t bring in enough to cover the basics.
I think one of the reasons I didn’t stay in newspaper journalism is that the pay was so appalling that I would call that a bit of an obstacle. I never made ends meet when I was working in that newspaper because I needed to own a car to be able to do the job. They said you don't have to but you kind of did. You just couldn’t do it on public transport. It wasn’t possible.
So yeah, I never ever made ends meet in that job, so I think that was a bit of a barrier to be honest. If you are living with your parents or get funded in some other way then maybe it’s different.
You need money to survive. To grow your career. But that’s not the only thing. You also need a whole heap of interpersonal skills because most jobs expose us to people outside our social bubble. Especially if you just graduated from college.
This initial lack of experience can be a major obstacle. Until - like L. - you earn the expertise you need to thrive through learning on the job. But that path isn’t always smooth.
Maybe a lack of knowledge of business at the beginning as well [was a challenge]… Not really having a clue of how to get clients was quite an obstacle. I think… I didn’t do any business courses at school. I think it would have been very useful if I’d known about a lot of the stuff I know now. It would have been easier to build the business faster.
It’s ridiculous… So I think learning that organically by talking to other business owners is quite a slow way to do it. I think maybe doing a course... but obviously you don’t know what you don’t know.
Sometimes skills aren’t the only obstacle.
I still find today that… I sometimes find myself into environments where it would still be a bonus to be a man. I think especially in rooms full of older men it would be useful to be one of the lads and have banter and not be the only woman in the room.
Because you don’t want to draw attention to the fact you’re the only woman in the room but... somebody usually does. So you feel that you have that option to try and be one of the blokes or just capitalize on the fact that you’re a woman which can sometimes be an advantage. It’s difficult to know how to play it sometimes.
I asked L. how she handled that.
Uhm… I think I put on my ultra confident face and talk louder.
I have this voice - which I call my “talking to children” voice - which is louder and more serious and I use that more. I just make myself heard a lot more.
I really hate actually being in meetings and having to interrupt and speak over other people but sometimes that’s what you have to do in those situations to get your point across. Or even have any sort of presence in the meeting. So I force myself to do it.
Which I wouldn’t do in a room full of women. Because I wouldn’t feel the need.
As someone who’s more at ease listening, I really related to this. I still struggle breaking into conversations because it goes against my deeply ingrained sense of… Well, I suppose we can call it politeness. Or what feels like politeness anyway.
I asked L. how she learned to do this. How she learned to put aside personal discomfort and make herself heard.
I honestly think it comes out of a course I did in NLP [Neuro Linguistic Programming]. Which I don’t tend to say a lot because people have really weird associations. I’m really troubled by NLP because I can’t find enough evidence that it works, scientific evidence, but it worked for me. And that really irritates me. I want there to be studies that this technique works because of X and there just aren’t.
Some of it comes from psychotherapy and things like that. And I think that element of it, there is some evidence, but I think most of it really, is really discredited by the scientific community.
But yeah, I did quite a lot - as part of it I did some public speaking skills and building rapport skills and kind of sales techniques. It was all part of that and that's all really useful.
So mirroring and matching where you kind of adopt the pace and tone of the people you are with unless they are really down and depressed in which case you may try to lead the pack up a bit. Yeah, mostly match. So you match the attitude in the room, the tone.
It’s made a massive difference [to my career]. You know I did a professional mastermind… I wouldn’t of had the guts even to… Would I have had the guts?
I think I would have had the guts to apply for it but I don’t think I would have felt I was in a room with my peers. I think I would have felt less. But I think the NLP stuff really raised my confidence.
Stepping outside your comfort zone, doing the things that will make you grow - even when you don’t want to… Those are the things can catapult your career (and confidence) in those early years. And they can help when you face the challenge K. told me about.
K. recently made the shift from a very well paid corporate job to full-time entrepreneurship. And alongside the freedom and ownership that comes with building something you believe in, comes the necessity of people wrangling. Of figuring out when to stand your professional ground - and when to make allowances.
I’ve got a client who’s just given me some of the worst feedback. And I’m only a year in… but this is like the worst. He line-by-line rewrote sentences and made them so much worse. I don’t think I’m like the greatest writer of all time, but this is objectively much worse than what I wrote. I’m 100% sure of that and I don’t know how to handle this.
So client management is just a minefield when you are a freelancer. It’s just so nuanced and you’re just… So clients in particular. There’s a lot of challenges there.
I think I seek out mentorship big time to understand how to handle those better. And I think the other big thing is, overtime it gets easier. It will feel more like second nature. Clients are just giving you a hard time and you just get used to it and you just adapt to it.
I think a big thing for me has been… I think I lead with my emotions kind of. Which I think is helpful in a lot of ways because it helps empathize but it’s frustrating when someone makes you feel bad because fuck.
So when I got this terrible feedback, I had the most emotional response ever. I slammed my laptop, and I walked outside and I was like “Oh why.” And I think I’ve learned this about myself…
And I think it can be fun to be - like a character - but I think you have to develop some resilience and some mental toughness and really focus on that. And just get used that you’ll have to deal with like bullshit and stuff that you are not happy about. And you just need to brush it off.
That stuff used to bother me a lot more a year ago and it doesn’t bother me as much as it used to. I think you just get used to it. There’s this line: “It doesn't get easier but you get stronger.” So that’s how I feel about it.
We can’t control other people. We’ve got no say over their reactions, feelings, actions… And knowing how to respond in a way that’s true to you and your business… Well, I suspect it’s one of those things we have to keep working at because human interactions are complicated.
When L. worked for that small newspaper, she had to expertly trek through certain dynamics.
In the newsroom I would say there was definitely a very male vibe so… The only reason I would say it was an obstacle is because it was quite difficult to join with a lot of the camaraderie that went on so… a lot of football banter.
I’m not saying that only men watch football but you know, let’s be honest, I’m not interested in football. And just quite a sexist attitude to be honest, of putting women down and a very male-dominated environment.
I’m trying to think how many women… There were 4 female reporters so actually on the reporting side it was still 30/40% women but everyone else on that floor was blokes. There were more women in the sales and marketing bit. So yeah, just a kind of an ethos of “We would rather you were a man” essentially.
But I think it was in the Black Country which is probably a couple of decades behind other places in the UK I would say. So that was one obstacle.
L. used this experience to learn how to talk to almost anyone and to start her own UK-based marketing agency.
Looking different to most other people in the room is one challenge. Being different - like coming from a different field and professional background - is another. This is B.’s experience:
For me it’s always been feeling like I had to prove myself. In university I studied science and being in a marketing and communications world, it was particularly challenging because people would see that’s what I studied and then they’ll be like “Weeell, you can’t do marketing, you know. You are a science person.” And I was like “No, I can do both because I actually studied the marketing stuff too.” So that was really frustrating.
And then later, when I was in Toronto, one of the first jobs I got was for Maple Leaves Sports and Entertainment which is a huge sports franchise in Toronto. So they do the Toronto Maple Leafs, the Toronto Raptors and all of those guys. After I left and I started applying for jobs, I found out that a few interviews that I got invited to, they literally only invited me because they thought I could get them Leafs tickets. They weren’t even interested in me as a candidate, they just wanted to see if they could get tickets from me. So that was really frustrating.
So it was just a lot of proving myself and showing that I can do the job which - with a resume and a cover letter - is hard to show because you can write whatever the hell you want.
The jobs that I actually loved the most were the jobs where I had to actually do an assignment as part of the hiring process. So like with Maple Leaf Sports, the second round of interviews they gave us a scenario and we had to present what we would do if we had the job.
So for me that was the best because it got to show them that I actually knew what I was doing professionally. It was tedious because obviously you had to go through the application process and then it’s like “Ok if I get the job it’s because they saw I can do the job. Not because they think I can do the job.”
It’s just a completely different mindset kind of thing.
These skills served B. well when she first started freelancing.
I started applying for these jobs on Craigslist and they were like “Yeah, we don’t need your resume. We just need to know you can do your thing.”
It was like “Wait a minute, you mean suddenly I don’t need to show you my resume? It was like... what!?”
It was disorienting but also exciting because suddenly I wouldn’t be judged on something on a piece of paper. It was literally: I did this job, ok you did a good job, now we are hiring you.
And people would hire you on the basis of experience and merit as opposed to something else that’s completely arbitrary.
I had to learn more about that. About the feelings around switching from resume-based hiring to competence based hiring. Because when I made my own transition into entrepreneurship, this mindset - and reality - shift was better than I could have imagined.
It was relief for one.
It was exciting because for the first time, it didn’t matter if I had two years of experience or I had ten years of experience. It was about the work that I could do.
On the one hand that’s a little frustrating because when you are fighting with kids who are 25 years old, it’s daunting.
But on the other hand it’s like “finally.” You’re getting the recognition because you are good at your job not because you spent 10 years at a company or because of whatever arbitrary piece of information they want to pick.
Distilling your experience down into a neat resume is hard - especially if you’ve worked abroad, changed industries, freelanced, and generally shied away from the “done thing.”
Still… sometimes the path you start walking when you start your career isn’t the one you end up on. It’s what happened with T. She started working in the fashion industry but, after a few years, transitioned into an industry with more opportunities.
Ooof. This is going to be a little bit controversial because coming from where I am and my background and everything, and working in America I think… given with the whole feminist movement and female empowerment thing that’s going on these days... I think it can be quite a sensitive issue.
But one of the reasons why I considered pursuing the jewelry industry after several points of frustration in the fashion industry was the fact that I realized… very early on I realized that being female, brown, Asian and short, wasn’t going to work very well for me in the fashion industry. You know… So I had to quickly figure out a way of how to navigate my way through that…
Having said that, I’m also quite a resilient person. I come from a family of entrepreneurs. My parents are not of anything but they started working for themselves from quite an early age and are quite resilient, understanding that in order to have a better life, they had to go from employee to entrepreneur.
So in terms of overcoming challenges I think I had a good background of being a resilient person and understanding what the… not even the weaknesses but what the objections were against me and what I represent and just try to find a way around that.
And I think quite proudly of myself today... I think I’ve done quite well in terms of finding a job that I love and being in a career that I can enjoy.
I couldn’t help but wonder… What effect does that have? How does it make you feel and affect a career trajectory?
You know what? I was 19 turning 20 at the time and so if I encountered that at the age that I am now I would probably be more resistant to it. But I encountered it at the age of 20 so I’ll probably say I was a lot more resilient and as malleable to it. So I was like “If this doesn’t work for you, then I’m going to try something else.”
[Today] I’ll probably be a bit more resistant.
[And to someone facing this] I would say… Just keep at it. Be resilient. Don’t be so accepting at what the status quo is telling you and just keep punching through the wall…
It’s a bit harsh… But at least from my experience that’s as much as I can say…
This advice used to drive me nuts. It felt so cold. So impossible to do. And then - after hearing it more times than it should have taken me to do something with it - it began to sink in. Push through sounds like such crappy advice but there’s truth to it…
It’s so true yeah! What are you going to do? You can’t sit and ponder on life. You just gotta do it.
The times in my life that I have been most effective, most satisfied, most successful are the times when I just focused and punched through the wall. Because nothing’s going to come easy.
It is the only thing that you can do. You can’t be brilliant without working for it. You can’t be brilliant, you can’t be good, you can’t be great, you can’t be fit, you can’t be sharp without working for it.
There aren’t shortcuts, as cliche as it sounds. Sometimes there’s luck too. Luck comes to you when you work for it.
I always keep it at the back of my mind that it didn’t come as easy as I wanted it to be. And I’m always on my toes and I’m always aware of what’s around me in order to make sure that I navigate through what’s up ahead in terms of business challenges and corporate adversities. And in terms of being in a position where I work for an American company but at the same time look after an Asian Pacific business that also has its own set of challenges whereby you have to deal with different countries and different cultures all the time.
Moving through this environment needs a special kind of navigation.
It’s almost… The simplified answer to that is: “You almost have to be a different person every single time.”
The non-simple answer to that is :“You have to adjust to what people are like. You have to adjust with how people are like but also make sure that you are staying true to yourself.”
So I always say to my team: “You need to be as much of a chameleon and as much of an honest person, a person of integrity, as you can be.”
I do a lot of business in Malaysia, in Singapore, in Australia, in the Philippines, Thailand… I report to a company that's based in Boston, MA. So I want to say that in any of those dealings that I have... I’m as different as a person as I am, as truthfully as I can be. It’s one of those things that’s easier to do than it is to explain.
It’s a fine - yet essential - line to walk.
Building a life, growing a career… These things don’t take place in a vacuum. They’re influenced by the way we see ourselves and the lives we imagine having. For A., the biggest challenge was seeing the future she could have.
I guess there’s probably some themes… I think there’s probably finite challenges like “I don’t have the skill set” or “I’m doing something for the first time.” “Or I’m not getting on with a coworker.” Like these things obviously happen.
But if I was to think thematically, I think the challenges may be more psychological in a way. What I mean by that is this:
When I first started working, I didn’t necessarily have a particular ambition. I didn’t know that I could join a company and eventually be a part of leadership. I didn’t know that anybody would take me seriously. I just wasn’t… It wasn’t a part of my psychology at the time.
And I think it sets you up really differently. Can I like swear? When you don’t think you’re hot shit. I think for some people they join a company and they are like “I’m going to be running this in 5 years”... It lets them have certain opportunities and be strategic. And I think for a lot of people… I mean I don’t necessarily think this is a gender thing, but I do think that for me it’s like built into them.
Like “I’m coming in and I’m going to take this thing. Whereas for me it was like “Oh I’m just lucky to have a job and I’m happy to be here.” and I think that kind of mindset probably… not set me back, but it put me on a different trajectory for a long time… for the beginning of my career and so I feel like I’ve done really well for myself.
I ended up going to grad school and I’m doing really well at H. I have a leadership position but I feel like the veil has kind of been pulled from my eyes in terms of my potential and my abilities.
And I’ll always wonder “What if I just thought a little bit differently about who I could be. Would I have asked for more opportunities or tried harder to get a position because you know what, maybe I’m not 100% of a fit but I’m 70% and I can totally figure it out. Yeah, just having that mindset might have been different?”
We talked about what changed. The answer wasn’t… Well, you can decide for yourself.
I have no idea [what changed]… I mean, probably a million different things.
think I was really lucky in that some of the people who were trying to get me to join this other company were just really good mentors and had that mind set and they saw something in me and believed in me.
And God bless them, they stoked that fire over the course of 6 years and helped me understand that yeah, I’m kind of smart and I’m kind of nice and I do good work and there’s potential for me to do things that are more than hella basic.
So I just honestly, I got lucky that I had the right people to help me feel supported.
Sometimes the biggest challenges - and the hardest thing to push though - is your own comfort zone. Other people can help. And so can reflection. That’s the path C. chose when she decided to face her biggest obstacle:
The unknown… The unknown is definitely scary.
It’s the most difficult thing for me because I like to control my environment. To keep things happy. For example, I will not expand the business until I know there’s harmony... and if we bring any more people in there would still be harmony.
I say this is my strength and my weakness because people are like, “Oh, there’s such great energy in your office. Everyone is changing and whatever.” And I’m like, “But we are still 4 people or 5 people.” And I almost refuse to grow because...
How can you grow and still keep your soul?
Because if we lose that, then we don’t want to grow.
So the real challenge I would say is… Usually the challenge is in me. Inside me. I feel like I’m wrestling through and accepting the realities of… “If you grow a business you are going to have these challenges of criticism and of people problems.” And it’s almost like, I’m afraid to leave what I’m trying to create... Utopia.
I’m afraid to grow because I’m so against - from my corporate time - maltreatment of people. Or unknowingly doing something that hurts someone’s career, because you weren’t paying attention enough. And that can be misconstrued in so many ways where people feel mistreated even if you have everyone trying to not mistreat you…
So it’s a weird control issue I have, I’d say. Definitely my biggest problem.
My biggest challenges have definitely been internal. I’ve fought against my fear and hubris and the chaotic unknown. So I asked C. how she handled it. How she moved past the problem when it was time to grow the business.
Right now it’s time to grow. This year we’re really focused on scaling and me getting out of the way. So we hired a consultant to help us. He said “If a CEO came into your business, what would they do?”
And I said “They would do this and this and this and I wrote this whole list. And I said, that’s exactly what they would do.”
And he said “Why aren’t you doing it?”
And I’m like “Because.”
So it’s really the practice of removing my emotions and my beliefs, putting them aside, and seeing the business as a separate entity.
I don’t know if that’s the “right” thing to do but I’m practicing it because I think it’s necessary for my sanity and the growth of the business. But I’m still in constant fear that the soul of us - and why people love us - is gonna weaken somehow if I let go of control.
But yeah. I’m getting outside help and I’m getting out of my own way and trying to see things effectively without my own crazy view.
I wondered if she noticed a difference. Partly because I thought it would be a good thing to ask about. Partly because she was talking about the things I’d been hiding from in my own business.
No. I mean… I still feel crazy. I guess it’s still too new. It’s February and we started seeing things differently this year — so I would have to see reality changing first. But inside I feel more paranoid because it’s so reverse of what I would naturally do. But I feel logically it’s the right thing to do. It’s weird. It’s a bizarre feeling.
It’s so weird when what you should do is the opposite of your gut… or what you would naturally, instinctively go towards so I’m like, “Alright, I’ll listen to you and do something different. I’m trying it.”
Change is hard. Especially when it comes hand in hand with a major life transition: moving to a new continent and re-starting your career from scratch. When D. left the US she had to build a network, find connections and build everything else up again.
My background is in political science and international relations. I thought I’d go into the state department. It’s what I wanted to do. I like research. I like thinking about solving problems and always thought my career would be in the public sector.
But I ended up managing an American think tank in Beijing, China then moving to Singapore and starting from scratch. There are no think tanks and NGOs - just government-led efforts- so I went back to the drawing board to figure out what I could actually do here.
I have a background in energy policy so I started going to a lot of energy events and networking. I ran an energy blog to engage with the wider community. Started networking with people.
In Asia it’s hard to get a job if you submit resumes. If you don’t check one box, they cast you aside. You basically have to talk to people. I met someone who introduced me to my current firm. I actually didn’t know what I was going to do until I started the job. It’s all about relationship building to be honest.
When someone submits something it’s really impersonal. There’s no way they’ll remember you. Your hit rate is so low. While you’ll be surprised how generous people are at making introduction. I think what this generation fears is interacting with people and being vulnerable- because you do have to be vulnerable.
But for me - because of my knowledge in the energy sector - I positioned meeting people as “Hey, do you want my thoughts on the energy sector?”
Growing up in the US no one teaches you these skills. You get a major and you go to a firm and you stay there for the rest of your life. In the real world, it’s not like that.
In an economic downturn, you have no job security. So there has to be something about you and the way you interact that makes people want to keep you. It’s not enough to be good at your job - you have to be exceptional.
When people like you and you are helpful and you do things correctly, the chances of getting opportunities is higher. I work very hard. I don’t really demand things. I want people to see for themselves that I deserve this promotion. My goal in life is not about money, nor is it about my title- it’s always been about “can I still learn from this job.”
We talked about what it took to forge a new career path. To excel and thrive even when things felt hard.
I’ve never really had a mentor in this sector (consulting). I’ve mostly done it through a lot of hard work. I do encounter some people who look down on me...
It’s mostly about knowing how to manage people and your interactions with them. At the end of the day, these challenges are learning experiences. What do I need to work on? How do I change this?
I came across situations where people were condescending and didn’t think I could do the job. And my personality is, if someone is looking down on me I’ll prove them wrong. I’ll go far and above.
I think that really helps. I would rather compete one on one, compete on merit than anything else. I don’t want a pity party and I’ll never complain because I’m a woman.
I guess in Asia things are more patriarchal. It’s always been about the male. The women you tend to find in Asia that have made it to some degree, they’ve done it through their own sheer willpower and their own merits. You will not say someone got it because they are a woman.
Career obstacles look different depending on where you are, the stage you’re at and what you hope to achieve. But certain challenges - like fitting everything into a mere 24 hours a day - are universal. For N. - as an entrepreneur and a mother of three - time remains one of the biggest obstacles.
… I wanna say lack of time. And I feel like everybody says that. But I really feel like I have no time. I feel like that’s the biggest thing in reality and emotionally also. It’s hard to focus and to feel like… It’s almost like I feel I’m kinda bratty: “It’s not fair. I have no time.”
Like “Of course… you know this person is better than me. I have no time!”
It’s almost like an excuse. But there’s the reality side of it and then there’s the emotional excuse side of it. I feel like it’s almost… And the fact that it’s hard. But it’s also hard because it’s a potential excuse. And then the actual emotion of feeling it’s not fair is also hard. I feel like that’s my hardest thing. Yeah. I think that’s the hardest.
Time is a scarce resource. Managing it properly, as you juggle multiple responsibilities, is hard. So how do you handle it?
I think… I’m still looking for a good project management software that can manage my projects and my time and I still haven’t found it. I think that would really help a lot. Hiring a virtual assistant has definitely been a huge help. Just getting rid of the tasks that I don’t have to be dealing with.
And also learning to focus… Not dealing with the stuff that I can’t do right now and focusing, almost like tunnel vision. Like “This is what I have to deal with right now.”
Yeah. I think that’s what’s helped the most.
And I also… you know what else has helped? Seeing how other people don’t necessarily have the time.
Other people will… they’ll be working a full time job and also trying to do what I’m doing [build a business]. Or also juggling other life things. Seeing that I’m not the only one who is struggling…
The emotional aspect of struggling with time is real. I wondered if N. saw a link between that and finding the right project management software.
Potentially. Because part of the emotional aspect is like the frazzled “I don’t even know what I’m meant to be working on and I feel like things are slipping through the cracks.”
I think that’s the… I know what’s in crisis. What I have to be dealing with. I know things that are important to me and exciting to me and what I should be dealing with. But the little things… like following up on things. But like... I don’t really know.
I think the more “peace of mind aspect.” That everything will get done when it’s supposed to be done. Or taken off the list. Or put to rest on time. I think that would help actually.
Just take it out of my brain. Put it on the screen. Put it on paper.
If a task is left undone, our brains have a tendency to keep returning to it, over and over, even when you’ve got other priorities on your mind. And this can easily catapult stress and anxiety to a whole other plane.
I’ve definitely felt the time struggle. Still do. With so many possibilities - and things you desperately want to do - it’s too easy to stretch yourself to your limits. To add more to-do’s to an already precariously topped up pile. And yet we only find out what we’re capable by pushing further than before…
… It’s a hard problem to solve. And it’s probably one of those obstacles that needs to be thought about - and treated - continuously.
I don’t know about you, but I find reading (and talking) about how other people solve their challenges and overcome key obstacles strangely cathartic.
It helps me step away from myself - from my problems - for a brief moment and remember that I’m not alone in the universe. That problems and hardships are as much of a human constant as you can get. But that there’s a lot of hope in there too. And help - as long as you’re willing to open yourself up for it.
P.S. Liked what you read? Catch the rest of this collection here.
* When I say “hard times” I’m strictly referring to relatively standard adult struggles - navigating personality clashes, impossible projects, tight deadlines, the constant background worry that the rug will be pulled out from underneath you, figuring out what and who you want to be etc.