The Different Journeys That Led to Your Current Role

This article is part 7 of our “Women in the workplace” collection. 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. 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. 

“What do you want to be when you grow up?”

I could never answer that question. I knew I definitely didn’t want to be a teacher, but that’s where my conviction ended. 

And I never could have imagined - even when I started college - that I’ll be doing what I am now. That’s why I’m fascinated by the different paths we take to get to our careers… 

Was it easier for other people? Cleaner? Just as complicated? Do some people have a naturally simpler time choosing what they want to do with their lives?

How did you end up with your current job?

This simple question seemed like the obvious place to start. 

Unlike me, C. knew what she wanted to do for a while. Still, she took the indirect path to it. 

“I grew up wanting to join the Peace Corps and save the world”

It’s a long story. I knew I wanted to start a business when I was in college... 

But before that,  I grew up wanting to join the Peace Corps and save the world (and all that stuff)... because your brain thinks that’s what it takes to “save the world” when you’re a kid. You see people in pain and you want to help them. 

And then you eventually grow up and find that things are way more complicated — and that people are more complicated.

So I studied journalism. I believed strongly in understanding people, and sharing the stories of people so everyone can understand each other more. That way of impacting people made more sense to me. Empowering others to help each other. That was really my goal. 

In my study of journalism - I decided to double major in business - and I realized, I actually have a knack for business and I didn’t know why… I won every business competition in school and I was always the one leading the groups… And that was very surprising for me because I was always quiet and shy and very, very stereotypically “feminine” (aka too sweet) 

… So I got lots of criticism when I was put into these groups to lead.

I fought with a guy once who said to me “You were only chosen because the teacher thinks you’re hot.” And I was like “Really? That was the ONLY reason he chose me?” 

He said to me, “You’re just there to sit there and look pretty.” 

I said: “You’re just upset you weren’t chosen.” But I still heard him out because I was curious why he thought what he thought. 

Anyway, it took me a long time to believe I was qualified myself. 

Even though I had an offer with funds to start a business,  I said “I’m not ready to start a business yet. I need to learn. I need to go in the real world and learn before I can do it right. And then I joined a giant corporation as one of many. I look back and see this as the biggest mistake, but also the best thing I did, because the mistake led me to learn so much and realize  that I was meant to be doing something else. 

I stayed in corporate life for a long time feeling really lost and thought, “Why am I not learning what I want to learn in this corporate life?” And I was so frustrated and never found a mentor that I could really look up to, and never found a culture that I felt was the limitless “I can become what I want to be here.”

So I felt really limited.  So I decided to start a business that was really focused on culture. On building the culture that I always wanted, which is something that is people-focused. 

We always talk about individual growth here in our business, and if it ever makes sense for someone to not be here, I’m the first to say they need to go somewhere else because it doesn’t make sense for them. Even if it makes sense for a business. So we always prioritize the people’s well being.

I believe a lot of people want a better life in their work so I’ve...That’s my primary focus.

 And we are all kind of uncomfortably growing.

Not finding what she was looking for out in the world, C. set out to build a company that could give her the career she craved. 

K. followed a similar path. 

“Can you call what I do a job? I feel like I’m a rogue agent…”

Jobs - and careers - don’t look like they used to. But at the start, K. prepared for adult life by going the traditional route. 

When I was in college, I was working full time in marketing at start ups just doing performance marketing. When you are in a start-up and you’re on a marketing team you do any kind of marketing that’s around. You have a role - I think I was like a partnership manager - but I did like 20 different things. 

After that, I wanted to make more money so I sold out and worked at big companies who were like… recruited Ivy League kids and then they were like “We’ll give you the stars and the world” but the positions were quite boring. They were really well paid and really boring. 

I found that the more I got paid, the more I was like “No, I don’t like this work.” So I decided to… 

So I tried this a couple of times, IBM and then Walmart so I quit and now I do this [freelancing] because I was travelling and needed to make money so I was like… Oh, I’ll just freelance on Upwork. And then I really liked copywriting ‘cause I always liked writing and marketing…

K. ended up quitting corporate because the work wasn’t interesting or challenging enough. To keep her brain - and herself - happy, she went out on her own determined to build the fulfilling career she couldn’t find elsewhere.

What happens when you don’t fit the mould 

B. also started life in corporate, before transitioning into freelancing and then starting her own business. 

I couldn’t find a corporate job actually… Despite having applied to numerous jobs for something like…

… So it was after we moved from Toronto to Vancouver so I had applied for jobs from Toronto and nothing happened and then we moved and for another 6 to 8 months I kept applying for jobs and I wasn’t getting anywhere and then I just started my own thing. 

When you move cities, you suddenly find yourself into a whole new situation. The connections you had are gone. You’re looking for work alongside everyone else - and winning at the resume game becomes an almost impossible situation. 

I felt angry…  Partly because coming from Toronto where most of the corporate offices are located and then moving to Vancouver where there are, in comparison, very few corporate office, it was very frustrating because I never imagined I would start my own business. 

It was frustrating from that point of view because my options were so limited but it was also really scary because as the primary breadwinner it was like “How the hell am I going to support us?”

Because my partner found a job but it was like nowhere near enough to cover both of us so it was really scary from that perspective. And in terms of building my business, to be perfectly honest, I didn’t even know that I was doing it. For me it was just passing the time. 

I was getting jobs, whatever jobs I could. I was writing blogs for $15 and it didn’t bother me because I didn’t look at it as a job. I looked at it as something easy to do while I was looking for work. 

I fell into freelancing in a similar way. After moving to the States from the UK, I picked up a few content writing gigs while figuring out how to build a professional career here. As an adult, I’d stopped imagining running my own business a long time ago. I wondered if B. had thought about it. 

I did. But I never really knew how. I never really knew what I would do. I just didn’t… 

You know how some people are very entrepreneurial and they are like “I’m going to do this!” and whatever. For me it wasn’t like that. I was just answering these ads and I was getting the jobs because they were $15 bucks and I was not caring what they were and not thinking about it from a jobs perspective. And then I remember after 6 to 8 months, I looked at my boyfriend and I said “What are we going to do? I can’t find a job.” And he said “Well actually you kind of had.” Meaning this freelance stuff.

So that’s when I stopped looking for work. 

So many of us end up in corporate, at one time or another. I wondered how it happened for B. 

I wanted to be a doctor but my grades weren’t up to par and whenever. I did the practice MCATS. I did terribly so it was quite obvious I was never going to make it to medical school. 

So I’d had corporate summer school jobs and when I looked at taking a postgraduate college program, corporate communications was all that really interested me so I studied that for a year. And then I got an internship in LA, and then when I came back I just started applying for jobs and that was it. 

It was the kind of thing you did as a sensible adult. 

It was like “Ok. Your lifelong dream of becoming a doctor is not going to come true so now what?” 

And my sister - and I don’t even know what the hell she studied at university - she did the same kind of thing where she went back to school and did a postgraduate one year thing in HR. That’s where I got the idea from because my science brain didn’t even, I didn’t even know what a press release was until I studied it. 

So I just kind of followed in her footsteps. I knew HR wasn’t interesting to me so corporate communications was a little bit of marketing stuff with a little bit of PR stuff and event stuff. 

It was kind of like everything that I…. I always liked writing for fun, I just never knew it was a job. I loved planning birthday parties. Also never knew it was a job. I loved all of those little things so when I found out it was work and I could study corporate communications and do this I was like… “Oh wow.”

Careers are not built in a vacuum

Sometimes major transitions - like moving cities or countries - affect what our careers look like. And sometimes it’s global events - like 08, the year L. started her business - and personal events like becoming a parent.  

I guess my background is... I started out as a journalist and I worked at a newspaper for like two years and then I went and freelanced, helped my husband’s photography business. I was doing freelance articles for magazines and as part of setting up this photography business we got commercial contracts. 

People wanted to do websites and brochures and they wanted people to do copy. I wanted to do it and that’s how I got into copywriting and yeah… I’ve been running my own business since like 2008 and employing myself as a copywriter.

Essentially 08 was when I named my company. I already had work. But essentially I lost all my clients around about that time just because of the recession, so yeah, it was starting again slowly because I also had my son in 2008. So I was only doing one project at a time and only working evenings and weekends so it wasn’t like I needed a full client roster. But yeah, 2008 was tough. 

N.’s journey was affected by moving countries, becoming a parent and the closure of the agency she worked for. 

In terms of moving from agency to freelance, I was working in a startup branding agency and like most start ups they failed. It was a partnership issue more than a success issue. So we decided ok, if I’m going to be freelancing then lets move to Israel. And then once we moved here we were like “Ok. Let’s stay here.” I know, it’s crazy. Like we didn’t do a lot of paperwork or anything. We didn’t leave the way you’re supposed to leave.

So once I was here, my only option was to freelance. Which is not quite true but… Basically they let me take my baby to work at the agency and then it was such a blessing that they closed because she’d reached the point - she was 3 months - where she’d start crawling soon and doing all sorts of stuff that you can’t do in a workplace. 

So I was like - should I quit? Should I not? So I was like… Oh. You have no more job. Now you have to freelance. That was the real motivation.

Cause I actually did get a job offer when we came here and it was really like… Yeah, I want to be able to be with my kids and work. 

I don’t have kids. But the main reason I decided to build my own business was so that - if I ever did - I’d have the freedom to do well-paid work I loved that I could organize around my life. I asked N. what stopped her from finding another agency job in Israel. 

It was more than the language barrier for me. I could get over that. I really can. And I love being in a work environment. I don’t actually fit the profile of the freelancer who wants to be a freelancer because she wants to be a freelancer. 

I’m 100% doing it for my kids. It was 100% so that I could like nurse my babies and not send them to daycare and blah blah blah... 

… My dream is kind of creating an agency where mothers can bring their kids. So I’m still struggling with how that would work. How I would have different ages of kids… ‘Cause most people send their kids to school at a certain point so it gets a little tricky with that. But I do like the idea of being able to collaborate and be together. I do miss that aspect of being at an agency. But it’s nice being able to make my own revenue instead of just being locked into a salary.

“I had a hard time finding connection”

A. switched jobs - pivoting careers - after struggling for a while. It took her almost 10 months after hearing about a potential opportunity to decide to make the shift. 

I currently work at a company which does non-medical care for seniors. I work with our support team that helps the day-to-day contact with clients. I had a bunch of relevant experience in my past which made me an interesting fit for a role that was opening up right when I joined.

When I started, I’d actually been working in management consulting for a long while and just had a hard time finding connection there for a lot of reasons. 

You’re spending so much time on projects there that maybe if they don’t resonate with you emotionally or spiritually or morally or all of these things... I just couldn't imagine living my whole life, spending my whole time, on these things I just wasn’t very passionate about. And so when I got to that point, I was like “I really should consider other opportunities.”

And I remembered getting a LinkedIn notification from one of the recruiters here and I probably sat on it for like 8-10 months but when I was ready to make the jump, it felt like the right choice because it was a company that 1. resonated with my past experiences and skill sets and 2. With my ability to work on something that could really make a difference and that I would feel good about doing every day. That I’d wake up excited to come into work. And it all worked out. They hired me and here I am. 

I wondered what made her take that step. What made her decide she was ready to pursue something different. 

I think honestly I’d come to a point where I was just feeling bad every day and I let it get that far because I thought “Work is a job and you do it because you don’t go hungry and it’s not pleasant.”

And I just thought that’s what being a grown up was but I got to a point where my relationship was suffering, my relationship with my friends was suffering and I had to make a choice. 

Actually… I didn’t make the choice because I was interested in the company. I made the choice because I as a human being needed to do something different if I was going to live a life. And [this company] had just stood out to me in my mind. I mean I don’t respond to anything on LinkedIn- I delete everything- but there was something about this so I kept it in my inbox. And then when the time came it was one of the first places I reached out to.

We talked about the other options A. came across and considered at the time. 

I talked to three companies. It was this one, one that was a makeup related company for women of color and particularly black women - it was actually black women - and so these were the two front runners. 

And in looking for references I reached out to someone I used to work with in the past. And he and a bunch of folks from my old company-  we really worked really tightly together - they started a company for themselves and in the end I was choosing between [current company] and that company that my old coworkers used to run. So yeah.

That was all. I didn’t do like a broad outreach or deep dive into all the positions. It was really just those.

Working with people you get on with - people that help draw out the best in you - is a gift. So I wondered what drove A. to chose her current job. 

It was such a hard decision. 

Obviously, there’s something very comfortable about working with people with who you know you work really well together. It’s great to go into work every day and be like “I love these people.” 

And I knew I would have that in the other company but the challenge with that company was that it was essentially online marketing and advertising and that was not where my heart was. So my heart was with those people but I had no passion for the topic. 

And just coming off of consulting, where every day I just couldn’t tell why I was doing this… It just didn’t make sense to jump from one thing I wasn’t passionate about to another thing I wasn’t passionate about. Whereas [current company] and being in service of others- that felt really good. 

Decisions are made up of gains and sacrifices. They have a cost as well as a win - and we need to be ready to live with both. 

When opportunity comes a-knocking

After moving countries, T. used a contact to land her current job.

I joined our company, which is a Boston, American Headquartered Diamond Jewellry company years ago. Basically I had a contact from this company that I’d known prior to joining 7 years ago. I was at a time in my career when I was looking to go back into the jewelry industry and I reached out to her and said “You know, I’m looking for a change. Is there anything that you might…?” 

You know, I emailed a whole group of companies within the same industry- the jewelry industry and I said, you know, I’ve been out of the jewelry industry for about 2 and a half years now and I’m looking to go back in. Is there anything that’s relevant?

And with this company, I reached out to someone that I’d known in my past life when I lived in the US and they said “Yep. Perfect timing. Reach out to us, send us your resume, let's go and talk.”

And that was pretty much 7 years ago.

Basically I started my career in the jewelry industry in 2003, initially working for a manufacturing company that had good distribution in the United States through the department store channel like Nordstrom and eventually working with Elizabeth Taylor’s Jewelry company and then during the 2009 Global Financial Crisis I was put in a situation where I could not renew my work visa in the US so I had to leave the United States because I was unable to renew my work visa and I worked in the marketing division of a beverage company in Singapore. 

I was born and raised in the Philippines and my family has been in the car manufacturing and car distribution business for a very long time. Typical to any Asian family, second gen, third gen, didn’t want to work for the family business. I wanted to go out on my own. 

Realizing that being in the Philippines which has a very strong influence by the American culture I wanted to move to America, to the United States and find a job in fashion or something related to fashion. Tried my luck for a couple of months, wasn’t really succeeding in any of that area and then a good friend referred me to consider looking at the jewelry influence because to a level it was still an interesting business so I started applying for you know, jobs in the jewelry industry. So met a… at the very young age of 20, met several companies but a company that I thought I could have a good start to a career in and then basically signed up for them.

[I found them ] through interviews. I sent resumes online. I don’t think LinkedIn was around in 2003, I’m not sure about that but… I don’t think so… But there was some version of a job posting site and I was sending a whole bunch of things out into the world and seeing what stuck. But I was very specific to the industries that I wanted to go after.

And it wasn’t until someone explained to me that jewelry and accessories manufacturing and distribution was something that I could get into, and then I started looking for jobs that were related to that. 

Moving countries and building up your connections - again - isn’t easy. I asked T. how she did it. 

Good question. I basically went out as much as I could, as often as I could and took the courage to meet the people I had to. I don’t think there was a very specific strategy on that except that if I met someone who I thought was aligned to the level of interest that I had, in terms of the industry that I wanted to go after, I pursued my curiosity on it.

I wish I had a formula I could give you but I look at myself now, I’m 36 turning 37. I started my career at the age of 20. Back then, I didn’t have a confident and specific strategy on how to approach career progression but I just followed my curiosity. 

T. focused on honing relationships and those relationships helped guide the course of her career. 

When I think back on my own journey, relationships have a huge role to play. I can connect the dots of my growth to two people who took a chance on me very early on and went on to refer me to others. Without them, I wouldn’t be where I am and this collection would not exist. 

Embracing your own career journey

When I was younger, I had a very linear vision of what my career and life would look like. There were big, specific milestones to meet. Neat check boxes of achievements to tick. Specific ages to reach all this by. 

None of it really worked out the way I imagined....

… Mostly because the story I told myself about the life I wanted, wasn’t what I really wished for at all. It was someone else’s story. A tale built from fragments of family expectations, other people’s ideas of a perfect life and my own half-thought out ideas. It was pretty. But it wasn’t me. 

Maybe you’ve known exactly what you want since you were 6 years old. Maybe you still aren’t really sure where you belong. I don’t have anything wiser to add than what the wonderful people I interviewed mentioned already, but I will leave you with this thought from A.:

You own your destiny more than anybody else.