In March of 2025 I rejoined the workforce after a career break due to burnout. I picked up a fixed term contract facilitated by someone I trusted not to mess me around. I set boundaries, and went into the project knowing that it was not the final answer, but also that having it on my CV would be a good way to get me out of the “large corporate and FinTech” pigeon hole I was landing in. By October of 2025 I could see the end of the contract coming, and I knew it was time to start looking for what would come next. What followed has been enlightening, humbling, exhilarating, and one of the more stressful decisions I’ve had to make.
Even compared to “do I move overseas for a couple of years?” and “should I quit without a backup plan (other than a healthy savings account) because I’m burnt out?”
The background
In early 2024 I was miserable. I was always tired. The nerves in my legs would burn on hot days, cold days, good days, and bad days. To the point where I, as a woman who doesn’t always recognise pain, was complaining. I had a generalised inflammation response in my skin which meant that if my dog wagged his tail against my legs it hurt like pressing against a fresh bruise. I was fighting a losing battle with acne, bad enough to be worth commenting on by those closest to me. I was working too hard, and giving up on the things I found fun or meaningful. Going to Church was a chore. My fitness suffered. My immune system was low enough that I was actually susceptible to the Flu. In 2023 that Flu had caused an ear infection bad enough to cause bleeding (the fact that I won’t go to a doctor until I’m literally bleeding from the ears is its own issue).
I may have touched on some of these things in Lessons Learned but I feel it is important to re-iterate where I was. Even more important, that I couldn’t tell how bad it was until I stepped out of the experience. I do not blame those around me for missing the signs, I’m really good at looking okay even when I’m not. Part of being a neurosparkly woman in a male dominated industry.
So, when I left due to burnout I wasn’t making up a diagnosis. The physical ramifications of the chronic stress I was putting myself through were real. When I took them to the doctor we did a slew of standard blood tests and I came out “healthy”. I am bad at doctors (refer back to bleeding ears) and I wasn’t able to express the disquiet properly, and really never know what I’m supposed to say to them. So I read the “try to get 6-8 hours of sleep”, took it with a pinch of salt, and decided that the medical route was not the answer. Why? Because the amount of emotional energy I would have to put into the process of dealing with doctors was too high.
I took that into account when picking up the next step, and it was a good thing. Over the last two years I have significantly reduced the amount of pain I face on a daily basis. Migraines are no longer a “multiple times a week” occurrence, rather they happen if I have a particularly bad day and it is just the wrong weather. My generalised inflammation has reduced enough that when it does flare up I am surprised again, and the nerves are still flaring from time to time, but mostly when it is really hot and I haven’t been sleeping.
I’m not back to 100% yet, but I can at least say that I have been improving whilst working. Which I wasn’t sure would actually be possible.
Inevitable change
Being in a happy place with my work was great, but I knew from the start that it was a stop gap. This would be a portfolio piece to prove that I can use standard modern technologies. I would obviously build to a high standard, because I have high standards for myself. I would not be running the service in the long term, and that was understood. So, in October 2025, knowing that the job market was not the same as it was in 2021/2022 when it was overwhelmingly open, I opened myself up to the interview process for my next full time position.
I started in mid October (even talking to recruiters on my birthday) with the goal of knowing at the beginning of December what I would be doing in January. I figured the timeline of a month and a half would give me the space I needed to balance a productive work environment with job interviews. My maths wasn’t far off on that. The process as a whole, though, was a fascinating set of lessons, stressors, sleepless nights, and ranting at family.
Before accepting an interview
Yes. You read that right. For the most part in my job search it has been about accepting an interview. I did apply to a couple of places, but only one of those turned into anything real, and the steps I followed were more or less the same. So you could say “before applying” for them.
Before the first meeting is scheduled in my calendar, I needed certain information. Much of that is covered in Recruiting Me, and I stand by those statements. I ensured that the product was something which matched my values. That the company has an online presence I could find and understand. That the terms of the engagement were within my own wheelhouse.
In one case I applied for a role which was advertised as hybrid, thinking that it might be worth the irregular commute if they were awesome enough. In one case the role was advertised as fully remote from the start. In the third case, I told a recruiter I wasn’t up for a hybrid role with a long commute, and the company asked if they could speak with me anyway. At which point I was curious enough to say yes, because they met the other criteria I was looking for.
The process
I have an odd view on interviews. It comes from having learned to interact with people and communicate clearly, as well as having built what feels at times like a level of arrogance which I can frame as confidence.
My view is that I should never have to prep for the technical part of an interview unless there is actually going to be code involved, and even then my prep will be limited to setting up a clean project and workspace with the right languages and frameworks ready to go. Of the three loops I was running in parallel only one required coding, and there it was really far more talking about problems and code than writing it, since they allowed me to use AI rather than try and type on the fly.
I do prep for each interview though. I go through my list of questions about a company, what I have already found on their website, I make sure that I know enough about the place to have a good conversation. My own work history is fresh in my mind, and I am ready to rattle it off with whatever focus I am asked for. I look up the people involved on LinkedIn, on the company website, or I google them. I come into the session ready to talk up my skills, make the day-to-day sound interesting, and learn more about the people on the other side.
Interviews go both ways. If a person is condescending or rude to me in the interview, I make a mark against that company as a whole. I can get away with this because I interview for senior roles. Usually I will be reporting directly to a CTO or Head of Engineering, which means I am being interviewed by business leaders and senior staff. Not by the juniors or those who are not driving culture and direction of the product. I also make sure to have questions to ask people in those interviews – often in a very casual way. Conversation is so much better for getting honest responses from people than direct questions in many cases. Particularly cultural.
I see horror stories of people going through six rounds of complex and awful interview and also having to do a take-home task, and then not getting the job. I don’t know if it is that I pre-screen those out of my loop or what, but my favourite places don’t do that.
You start with the two way sales pitch, this is particularly important when you didn’t apply, you rather accepted an invitation. This is a conversation with a relatively senior, very knowledgeable member of the hiring team. Frequently the Hiring Manager. They sell the product, ways of work, and company culture, and you sell your skills. If they look like they will fit and you both agree that this is a decision worth pursuing it moves on to the next stage. If you clash, or something goes wrong, you might end the loop here.
Step two is technical. This is often a two or more hour interview where you dive into the tech stuff that matters to the hiring team. Sometimes you will have more than one technical session, that is pretty reasonable, and allows the company a chance to get to know your skills. This is the bit I do not prep for. I do make sure to ask whether it will be coding etc, but these people want to know what my skill set is on the daily, not what it looks like after I crammed a textbook full of smart responses. They want to know I can think, that I look at all aspects of a problem, that I can take feedback, that I can ask clarifying questions. As a candidate, these are the people you will be working with if you make it through to the end. If they rub you the wrong way, that’s a mark against the company. You want to be able to interact naturally with these people.
Step three is again senior leadership. Framed as cultural fit, these are the people you want to impress. They are frequently C-Suite executives in the company, and are not always deeply technical. If you can explain to a CFO with a B.Com how you are going to be a beneficial employee, you’ve snagged the communications ability you really need.
Some places or people skip steps one and two. Those are special, unusual, and fun. If you snag one of those and it turns into work, celebrate and go with the flow.
Offer negotiation
This is where I fall apart. The things I would want to negotiate are often not on the table for change. Office policies, benefits, number of days of leave, these are far more important to me than the amount of money you are willing to give me. The most valuable resource in my life is time. I am offering you my time, how much are you willing to give back? I don’t know why we don’t negotiate these things, and believe me, I have tried pushing back on them, but it really doesn’t work out.
I don’t see much point in negotiating the money. If you didn’t give me a range or ask what I’m looking for at the beginning, then I would have asked about it, and so it would have come out. This means by the time there is a written offer in my inbox it already has a number I’m happy with on it. No one lost time in the interview for a role where I would be earning 80% of what I am looking for.
So why is this even a section? Because it isn’t just negotiation. It is also comparison. I’m arrogant remember, I don’t prep for interviews, because I’ve never needed to. No one has turned me away for a lack of ability to think technically. I come out the other end of the pipeline with an offer, a promise of an offer, or a result entirely unrelated to my own abilities. Which means if I go through three pipelines, I will likely have three competing offers. At which point it suddenly is very important to know exactly what I want and why. I’m not here to play them against one another, not unless it has been proven to me that they are willing to negotiate on a point and having a competing offer will serve to make my position clear.
Offers for me are compared not on money, but on softer aspects. Benefits, yes, but even more importantly the nature of the company. Will I be happy working with you? Am I going to burn myself out again? Am I going to be frustrated by chaos or poor communication? Do I know what work I will be doing? Can I already see the value I will add?
What I left out
In all three interview loops, across all the interviews, I was asked about my career break. The way the leaders asked, and the way the handled my response was one of the most important things to watch for in each loop. I knew I had made good choices because every time the question was asked with empathy. They wanted to know what steps I would be taking to avoid falling into burnout again. They wanted to know that I had actually learned a lesson, and they wanted to know that I would not compromise my health. This was unexpected, but gratifying.
The responses were also fascinating. Those who reflected back the “I’ve been there” lead me to read the offer with a different lens. Those who responded with a concern that the environment might be too “always on” triggered the red flag of micromanagement. They also clearly didn’t understand that most people are not expected to maintain and lead the same level of product and experience as I was at AWS. You aren’t big enough, distributed enough, or critical enough, for me to land in those circumstances again. Those who responded with understanding and acceptance that the boundaries I set would be sufficient gained my trust in a way I don’t think I could explain without this context. They place their trust in me to maintain my boundaries, and so I believe that they can be trusted to not barge through them.
Where to next?
This is being published in January of 2026. By which you might draw the conclusion that I received and accepted at least one offer. I felt, in November, that I should have received three offers. I came pretty close, until at the last minute one of the companies I had interviewed with decided they needed to let their new CTO get a bit more experience in the team before hiring someone like me into the “Lead DevOps” role that I was going for.
The good news with that was I didn’t have to compare two really cool places against each other. I could accept the offer which I had been leaving on tenterhooks. I could join people who happily claim “we want to change the world”. We are also self-described hippies, tree-huggers, and do-gooders. I’ve started diving into learning a new system architecture, tracking my own favourite “wait what?” moments, and all the other fun stuff that comes with a new job. Best of all, I’m getting to work in a team again. A team of super smart people who are relying on me to do my job, and who I already know are brilliant at theirs.
So here’s to the future, and whatever that holds with Ideaonomy.
Pippa Hillebrand 