How I got my career back on track

My career started pretty normally, I guess. I went to a respected university and finished a BSc. in computer science and an MBA with good grades. I was working as a student at a well respected international corporation and was offered a full time job. I was totally set up for success. Somehow, 12 years passed and I found myself in a dead-end job with a feeling that I’d missed out on my potential and I would never make up for lost time.

In this post I’ll share how I recovered from an unknowing attempt to kill my career, and how within a few years became a senior engineer with my eye on higher IC levels (maybe staff engineer in a couple of years? Keep your fingers crossed).

Image by uniquedesign52 on pixabay

Before we continue:

There is nothing wrong with “just” having a job and not a career. Even a mediocre tech job offers higher compensation than you would get elsewhere, and if you’re not particularly ambitious that is absolutely fine. You shouldn’t feel pressured into doing something you don’t want to do. What I do want you to take away from this post is:

  1. Make a conscious choice that is what you want. Don’t do “job” if what you want is a career.
  2. You can change your mind. Just because a “job” works for you now, it doesn’t mean you can’t have a career later.

How it started

After finishing school, my husband and I decided to move to a better location with more employment options, so I looked for a new job. I was young, with no real constraints and excellent credentials and within a month I had 3 offers. I took the highest offer and stayed there for 6 years.

While I was there I had 2 children and reduced my hours to make life easier. When I was ready to leave I was set on getting a job in a convenient location and if possible, part time. That seriously limited my options. I ended up working 80% in a small, local-market company about 5 minutes from home and stayed there for 6 years as well + a 3rd kid.

These are the simple facts. It doesn’t sound so bad – right? I was working, I was happy, I was being a “good mother”, what’s the problem?

Setting (no) direction

Would you tell me, please, which way I ought to go from here?”
“That depends a good deal on where you want to get to,” said the Cat.
“I don’t much care where–” said Alice.
“Then it doesn’t matter which way you go,” said the Cat.
“–so long as I get SOMEWHERE,” Alice added as an explanation.
“Oh, you’re sure to do that,” said the Cat, “if you only walk long enough.”

Perhaps one of the most quoted passage ever from Alice’s Adventures in Wonderland, I apologize for being so cliche.

Let’s start by looking at that second job right after university – it wasn’t bad, but I hadn’t made the choice to work there by considering how it would help my career. I didn’t really think of much of anything before looking for a job, I just sent my CV out using a placement service and took whatever they offered. The money was OK. The people were nice and professional. I learned a lot there. But I wasn’t progressing anywhere.

Now I had two problems

The first problem was that I did have other priorities besides work. I had 2 kids and… I was doing crafts. This was a bit more than just a hobby, I had a blog and in a way, I’d subconsciously bought in to the idea that tech wasn’t for women in general and for mothers in particular. Men plan for getting “old” in the tech industry by investing in real-estate, I was planning to transition into the crafts space – do workshops and sell crochet instructions online. OMG WHAT WAS I THINKING (probably this).

The second problem was that I knew I didn’t want to be a manager. When one of the team leads left (or was promoted? I don’t remember), they asked me if I wanted to be a manager and I said no. I wanted to be a software architect (this was before IC professional paths were common, senior IC wasn’t really a “thing”). When they did find a manager for my team, we discussed what I wanted to do and I remember they asked me why I wanted to be an architect, I was obviously not “passionate” about technology. I don’t know if they decided that path wasn’t right for me or just didn’t really care – but the facts were that they did not invite me to the right meetings (even though I told every relevant person they should invite me).

I’m a pretty confident person, sometimes stupidly confident (as you’ll see later), but this conversation about passion for technology really hit me. It is very true I don’t have a passion for “technology”. I couldn’t care less about the latest feature in .NET core or Java whatever version they’re up to now, and I’m bored to death by articles about the latest trendy framework. I will study a technology when I need it, but I’m not “passionate” about it.

Some exceptions apply: pattern matching in python is pretty cool or way back when they introduced null propagation in C#.

I am, however, passionate about creating good software designs and practices that will be flexible and understandable for future generations. Since then I’ve discovered things like Domain Driven Design (I feel was written for me :heart:) and other more abstract and non-technology specific software design principles beyond the design patterns I learned about in university. It’s a thing.

I don’t think they were gatekeeping – they probably thought they were being honest with me for my own good. But I was right and they were wrong and it set me back because I didn’t believe I could advance in the IC path without getting excited about… things I wasn’t excited about. I gave up, and again – it wasn’t a conscious decision, it’s just happened.

Aside: Why I didn’t want to be a manager

In truth, I wasn’t interested in being a babysitter. Today, I don’t think managing is babysitting exactly, but I didn’t, and still don’t, want that element of the job. Even today, as a senior engineer who’s very inclined to and very much enjoys mentoring – I’m glad that some stuff is out of my scope. Let them fight about the air conditioning without me.

I may find myself managing sometime in the future, and I think I’d be good at it. For now, I’m glad that I have the option to continue on the IC path which I’m more passionate about. There’s that word again.

Thank you, next

The next job I took was based on convenience – I wanted a place that would be relatively close to home and would enable me to pick up my kids. You have to remember this was quite a while ago, not many employers were open to the idea of flexible hours. I remember speaking with a recruiter from Microsoft (!) and telling them I would have to leave at 4PM to pick up my kids, and they wouldn’t even consider it. Today it would be a non-issue (at a place like that) you wouldn’t even have to ask.

I remember another employer telling me it would be fine for me to leave at 4PM, but my salary expectations were a bit high (they were not, I was deliberately setting them low because I wanted flexibility). Also I was expected to stay after 4PM if there was work to be done. Umm, what? They were surprised when I declined to continue the process. Fun times.

Finally I found the perfect situation. They were looking for a .NET expert, I was looking for a convenient place to work, the stars aligned in the sky and everything was great. I worked directly with the CEOs to define the product and implemented complex data migrations and delicate business logic (including the accounting system change I talked about here). After 4 years there the business was sold to a European media giant – I had a hand in that.

If this had been a startup my title would have been CTO and I would have made a lot of money off of the sale. As it was, I got a nice bonus equal to what I would probably get every year at a big tech company and some appreciation. I don’t blame anyone, it wasn’t a startup and it is what it is, I (thought I) knew what I’d signed up for.

Winds of change

While I worked for that company I had a 3rd kid and taking a 9 months maternity leave. During that time two important things happened:

The first was trying to create a startup. I hadn’t really given up on the crafts stuff, but I had realized it was stupid to take all my education and experience and switch to doing something that wouldn’t be very profitable. However, I did have an idea for an app in the crafts space that would be really cool and I thought might have a good market.

In between feeding all these kids I found time to write a business plan and realized that I could do this thing, but it wasn’t a high growth startup, it was a nice business. I would end up working really hard and earning as much as I would earn at a FAANG company without working so hard and with less chance of absolute failure. I gave up on that.

Which lead me to the second thing: I was doing my taxes and realized I wasn’t making enough money. I know, money doesn’t define your worth as a person – but it does indicate your worth in the job market. I was clearly being underpaid. The comment all my teachers added to my report cards had become true: I was wasting my potential.

9 months at home is a long time and I had a lot of time to think about what I wanted from life, and I knew it wasn’t feeding kids and driving them places. I mean, I would do that too, but I didn’t want it to be the most important and deciding factor in my life. I changed my mind, I wanted a career.

Into the lion’s den

We have a saying in Hebrew: “It’s better to be lions’ tail than the foxes’ head” and that’s what I felt – I’d been the foxes’ head for too long and it was time to go somewhere I could learn from other people who were smarter and more experienced than me and maybe… pay me what I thought I was worth.

Image by ArtTower on pixabay

Stupidly confident

I decided to go for a job in a FAANG company (or, actually, FAMGA as we don’t have a Netflix branch in these parts). I was told to try interviewing for other companies first, but I did the whole “cracking the coding interview” thing and thought I was well prepared. Ah, if I knew then what I know now.

I failed miserably.

My first mistake was starting at Google. My very first coding interview was at Google. WHAT WAS I THINKING. I didn’t even pass the screening interview. It was sad, really.

The second place I went was Facebook. The first screen I was so stressed the interviewer didn’t get a good signal, so I was offered a second screen. I passed the second one, but not the rest. They were looking for front-end engineers and instead of insisting on going through the full stack process (which I might have had a chance of passing) I agreed to do the front-end interview loop. My Javascript skills were not good enough. I did not fail so miserably there, but failed nonetheless.

Then there was Microsoft. I won’t go into the details of what happened there, but let’s just say I tried for 2 groups and was not accepted for any of them. By that time I was pretty well prepared, but I was so stressed I kept making stupid mistakes in areas I knew well.

I’d submitted my CV to Google, Facebook and Microsoft through people I knew, but since none of that worked out I started widening my search, and wasn’t getting any callbacks. I didn’t understand what was going on.

Tiers in tech

I’m sure there are parallels in how other tech markets work, but in Israel there are two separate paths for working in tech.

You can work at an international corporation (many of which have branches in Israel, not only in Tel-Aviv) or a startup aiming to conquer a global market. This type of company uses cutting edge processes and technologies and keeps up to date with the latest trends.

The other option is working at a local company, aimed at the local market. This could be the IT department at banks or companies like the one I was working in. These companies don’t usually lead technologically. And even if, by chance, they do apply modern technologies and procedures – no one will believe it or take you seriously.

I had gone from the first tier to the second tier, without realizing at all what that meant. I did excellent work, really. But it didn’t matter because I’d done it in a local, no-name company.

Turns out, that was why no one was getting back to me. Lucky for me, the company I worked for had been sold to that European media giant I told you about. Once I’d legitimately changed the name of my employer, I started getting calls. Amazing. But I still really wanted that multinational corporation.

Last(?) chance

Dropbox having a local branch was not well known in at the time, but it was in my search radius so I sent in my CV. Nothing. Then, somehow a connection through a friend’s relative surfaced, and they referred my CV. Another chance at a top-tier multinational! By then I was getting better at this type of interview, having made all those mistakes at Google and Facebook. I passed the screening interviews (two of them) and was moved on to the on-site interview. Exciting!

In the mean time, I got a chance to try for a 3rd group at Microsoft. And failed. Again.

By this point my mental state was less than amazing. I’d started out over confident in my abilities, and now I felt I would never get out of the mediocre situation I was in. I felt Dropbox was my last chance at what I really wanted and was totally losing it.

Help comes

A few months before any of this happened (but after I decided I wanted a career) I joined a group called Baot, Israel’s largest community of senior software engineers, data scientists and researchers who are women. This is an amazing group of women I’m proud to be part of. One of their many excellent programs is “finding your next job” which offers mock interviews, long term and ad-hoc mentoring.

This is a while ago and I was very stressed at the time so I don’t exactly remember who I talked to, but I was matched with the inspirational Hila Noga. I was sure this was it, it was my last chance, and said so. The gist of what Hila said was: You’ve got this. And if you don’t, there were other options. I’d been so locked in to the multinational corporation idea, that I didn’t really understand I could level-up by switching to another first tier company like a mid-sized startup, and even if I did end up pursuing FAANG – I would be starting from a better place.

That was what I needed to hear and internalize. This wasn’t my last chance. I showed up at Dropbox calm, collected and ready. And I got the offer.

How it went

I’m going to be honest even though this is a bit… uncomfortable for me: I didn’t do very well on the Dropbox interviews. I had no idea what I was doing in the system design interview. Add coming from a no-name company into the mix, and that did not inspire a lot of confidence.

I got the offer, but I was down-leveled (not that I knew what levels were at the time). I took the offer anyway. They made that decision based on the information they had, and I needed to get out of the career hole I’d dug myself into – so I guess it was a win-win. Still, I wasn’t positioned very well when I started.

Corporate life

Things weren’t easy, there were ups and downs. Sometimes I wondered what inspired me to want a “career” in the first place and if maybe that decision was wrong. I cried in the bathroom. It took time to get my bearings in this new environment.

About a year in, suddenly everything seemed to click – someone came over to where I was sitting (remember before COVID, when we could speak to people in person?) and asked me a question about something not directly related to something I was working on. Incredibly, I knew the answer. Click.

Aside: on being a working mom

Juggling work and kids is never easy. In my previous jobs I was working 80% at low pressure positions and it still wasn’t easy.

Dropbox, at the time, allowed for flexible hours and working from home a day a week (after COVID they switched to “virtual first”, in essence – full time working from home), so I could still juggle. However, since I decided I was going to focus more on work – I wanted to get help. Many forces coincided in a way that didn’t actually allow me to get help, and then COVID hit. By now, I’m working from home half the time, my youngest kid is 5 and my older kids can help, so pickup help became a non-issue.

However, just because I never got the chance doesn’t mean I wasn’t right. Get help. Outsource cleaning, cooking, daily pickups. Whatever you feel comfortable with and can afford. No one’s standing at the end of life handing out medals that say “I did it myself”.

Slowly, I built relationships, figured out how to work in an enormous and complex codebase, how to design stuff big and small and make things happen in a multi-team, multi-national settings. I helped improve team processes, I gave valuable code reviews. I wrote blog posts and gave public talks. I worked with amazing people I could learn from and discovered they had things they could learn from me as well.

It’s hard to be sure, but I think I arrived at Dropbox already a senior software engineer, I just had to prove it. I also think my particular talents and skills were well suited to Dropbox. Eventually I got the promotion to senior software engineer I totally deserved. Later I got a tech lead role I really wanted on a project I was very excited about. I’m not saying this to brag, I’m saying this because I’d gone from a head-of-foxes situation to the middle of a lion’s den (in a good way) and I was doing well. If I could do it, there might be hope for anyone! Take that imposter syndrome!

Image by RoyBuri on pixabay

Even after all that, it was hard to shake the feeling that I’d never catch up. I’m almost 40 and there are a lot of younger folks around who were way ahead of me. I didn’t let myself ruminate too much, because really – you can’t live your life comparing yourself to others, it’s not healthy. There will always be people who are better, smarter, with more drive than you. But it still hurt, a little pinch every once in a while.

How it’s going

Then my time to leave Dropbox came and I discovered just how much things had changed for me. I knew what I liked doing and what I saw myself doing in the future. I wanted more technological depth, more platform-y and less product-y work and I looked for something in that space.

I’d been a senior SWE and tech lead for a while and all these companies were taking me so seriously! The interviews weren’t easy, but I knew my way around them and got several excellent offers. They thought my blog posts and talks were impressive. They were considering me for technical leadership roles as if I was a real senior engineer! Which, I guess, I am.

Compare that to my many sad rejections just 4 years ago.

I’m not saying my next role won’t be challenging, because it will – but I feel up to it. It doesn’t matter that I “wasted” over 10 years, I’m here now and I’m ready.


So, there it is. This post is not very advice-y, because a lot of the advice I have to give has been covered by previous posts (How to ruin your career in 8 easy steps, Yet another guide to tech interviews), I just wanted to share my story in hope it makes someone believe that they can get out of a dead-end job if they want to.

Thank you to everyone who helped me along the way, there are too many to mention by name. I appreciate you all.