Kristine Howard: Lessons in Leadership, Making Your Own Luck, and Retiring Early

Meet Kristine Howard — a familiar name in the Aussie tech scene, with a career that’s taken her from developer to team leader, conference director, and most recently, Head of Developer Relations for APJ at AWS. These days, she’s semi-retired and focusing on board work and projects she’s passionate about. In this chat, she shares career insights, lessons in leadership, and what life looks like after stepping back from full-time work. Photo by: Joy M Lai.

Introduce yourself!

I’m Kris Howard, an American-Australian living in Sydney. I grew up in Indiana, worked in London in the dotcom boom, and eventually followed my Aussie boyfriend (now husband) Down Under. For the last 25 years my primary online home has been Web Goddess. It’s a slightly embarrassing name; it was a nickname a friend gave me because of how chronically online I was, before that was even a thing. That’s not my oldest website though! That honour belongs to Roald Dahl Fans. In uni, I built this site dedicated to my favourite author, and next year it will turn 30 years old. If I ever went on a quiz show, Roald Dahl would definitely be my special subject.

You’ve worn so many hats — engineer, analyst, director, thought leader. Looking back, which role was the most pivotal or taught you the most, and why?

It was the first time I went from an individual contributor to managing people. It was the most stressful year of my life, and I learned so much. I think the biggest shift was changing my mindset from personal achievement to succeeding as a team. I had to learn to get satisfaction from seeing others rise, and to figure out the best way I could support them and help multiply their efforts. For someone that loved to be in the spotlight, that wasn’t the easiest thing for me!

I also had to learn how to manage up and down at the same time, and to figure out how my team’s efforts fit into the bigger overall picture. And then there are the really hard parts, like giving critical feedback and communicating decisions that I didn’t always agree with. I was fortunate to have a couple mentors that really helped me level up quickly.

You’ve worked in both technical and leadership roles — how did you decide when it was time to shift gears? Any advice for someone trying to figure out the next step?

In my case, the shift was prompted by organisational changes at the company I worked for. I found that the manager on my team was leaving, and they offered me the chance to step up. I was nervous but figured that I could do a better job than an outside hire, who might wreck the great team culture we’d built.

I had a lot of support from the company CTO, and I was also invited into an internal leadership training course. I’m not going to lie – transitioning from being a colleague on Friday to being a manager who approves leave and pay rises on Monday is really difficult. In some ways, making that transition with a brand new team might be a little easier because you don’t come with any baggage. But I felt well supported, and my attitude was very much “I can endure anything for a year, right?”

My advice to anyone thinking about that switch is to take advantage of any internal resources they can: training courses, mentorship programs, secondments. And don’t forget, this isn’t a one-way door! I love Charity Majors’s metaphor of the engineer/manager pendulum. Switching back and forth is a totally valid approach. My next couple roles after that one were actually IC roles, before I eventually moved back to a manager role at AWS.

What did running YOW! teach you about what makes a great talk or speaker? Any advice for folks wanting to speak at conferences?

Actually I learned a lot from YOW even before I started working there! Back in 2014 I attended a YOW Night with Damian Conway on “Instantly Better Presentations” (you can watch it on YouTube) and it was the best 90 minutes of concentrated speaker advice I’ve ever seen. Later, I applied to YOW’s speaker training program and was lucky enough to score a full day workshop with Damian. I still regularly refer back to his advice.

When I worked at YOW, I was fortunate at the conferences to get to see talks from some of the smartest folks internationally and here in Oz, as well as attend hundreds of local meetups as part of my role. I learned that what makes a talk really memorable is the speaker’s unique point of view. I don’t remember any talks from vendor representatives parroting the latest corporate speaking points; what I remember are people sharing their own war stories (both positive and negative), their enthusiasm and passion for teaching something new, and their creativity and inventiveness in how they presented everyday topics.

You don’t have to have invented a new framework or be an expert to give a talk at a conference. You just have to be yourself, and put in the work (as in Damian’s video) to organise and craft the story you’re telling. I’ve also written a LinkedIn article with advice on how to get started.

Leading DevRel at AWS across Asia-Pacific and EMEA sounds huge. What were some of the unique challenges — and unexpected wins — of working at that scale?

Being part of a global team is exciting and you get to travel to exotic places, but it gets super hard to maintain any sort of work-life balance…especially when you’re outside North America or Europe. I love living in Sydney, but we often get screwed when it comes to timezones and off-sites. I’ve been on video calls at 11pm and 5am. I’ve spent a lot of time in hotel rooms and on airplanes. I’m pretty fortunate in that I have a lot of support from my partner, and thankfully we don’t have kids so I was able to have a flexible schedule. But just from a life perspective, it gets hard and exhausting.

Hiring was the other massive challenge. You have to contend with the language barrier, local laws and restrictions on who you can hire, local recruiters who don’t understand the nature of the roles you’re hiring for (thankfully never a problem with Lookahead!), and potentially getting thousands(!) of CVs when you’re hiring in a place like India. And then if you do manage to find the right candidate, you might have to contend with complex salary negotiation rules, work visas, local HR folks, and figuring out how to onboard someone in another timezone and language. My biggest victory: successfully getting a work visa for a candidate who was trying to GTFO of Belarus in the lead up to Russia’s attack on Ukraine. I am so proud of the folks I hired that have gone on to do amazing things, like Igor, Veliswa, Viktor, Wojtek, Cathy, and many others.

There were upsides too, of course. Some of the projects my team got to work on – owning the developer-focused tracks for thousands of attendees at the AWS Summits; contributing to new AWS region launches in countries like Switzerland and Malaysia; running developer events at AWS re:Invent in Las Vegas – are just an order of magnitude bigger than anything you’d get at most other orgs.

Within the APAC team, the project I’m most proud of was the Community Leaders Summit we hosted in Bangkok. We managed to pull together funding to bring 180+ folks from all around the region together for 2 days of learning from each other. I met people from Nepal, India, South Korea, New Zealand, Indonesia, Japan… many of whom had never had the opportunity to travel to an overseas conference before. I know that it had a huge impact on people’s lives and careers.

What’s one small thing you did consistently that had a big impact on your career over time?

I read an article recently about a scientific study into the nature of luck, and the conclusion was that “lucky people generate their own good fortune via four basic principles. They are skilled at creating and noticing chance opportunities, make lucky decisions by listening to their intuition, create self-fulfilling prophecies via positive expectations, and adopt a resilient attitude that transforms bad luck into good.”

It turns out that I naturally do those things, and they’ve had a huge impact on my career. I’m always eager to meet new people and do something new (even when it’s a bit scary), and that means I open myself up to opportunities. That’s how I ended up in London as a web developer; how I got the offer to become a manager; how I got my job at Canva; how I ended up running a team at AWS in Europe; and how I ended up getting my first board role. Just putting positive vibes out there, going to events, making connections, being open to possibility, and taking chances when they present themselves.

You’ve recently stepped back from full-time work — congrats! What inspired that decision, and what has surprised you most about this new chapter?

My husband and I had joked about early retirement for a long time, but it was never something I gave serious thought to. No one in my family ever retired before they were in their 60s, and anyway I figured I’d get terribly bored. Then 18 years ago we bought a house, and we started to get more serious about our finances. We began tracking our expenses and working on maximising our income. The big inflection point was when my husband got his job at Google. Within a few years, his stock options had offset our mortgage. We began investing all the excess into index funds, and once I got to Amazon I was contributing quite a bit as well.

A few years ago, we realised we had reached the point where it was a real possibility. My husband was burnt out at that point and very ready for a change, so he left his role in 2022 to be a full time house husband and part time craft beer tour guide. I stayed with AWS for a couple more years, mostly because I loved and enjoyed my job.

In 2024 though, I started to realise that the industry’s relentless focus on AI and LLMs above everything else was just not something that I’m particularly interested in. I also realised that my values had changed after the pandemic, and I was ready to slow down and step out of the spotlight. It felt like a good time to go. I figured I’d take six months to decompress, and then decide if I wanted to get a job. To my utter surprise, I’ve loved not working. I started volunteering, reading books from the library, working on my hobbies, reviving my blog… and in December someone offered me a job that normally I’d have jumped at, and I told them no. We have enough to do the things we want to do. It’s a privilege that I don’t take for granted, and I’m trying to give back as much as I can.

For folks in tech who are considering retiring early or stepping back — what advice would you give them? Anything you wish you had done sooner or differently?

Short answer: check out the blog post I wrote based on a talk I gave at Sydney Tech Leaders about financial independence for tech workers. That’ll get you started!

Beyond that, I think the decision you make with the biggest impact on your future financial health is in your choice of partner, if you have one. You should be having regular discussions about your combined finances, and know what you are working towards. I’m very lucky that my husband and I are both in alignment on our values, our approach to money, and our financial goals.

We’re not perfect though. Where we’ve made mistakes have been in things like putting assets in both of our names, only to find out later that it would have been more tax advantageous to put them in one or the other. (Being a dual citizen makes things tricky!) I also discovered an old student loan that hadn’t been paid off that was quietly accumulating interest, which was a painful one to deal with. But really these aren’t major (especially if you’ve built up a healthy emergency fund), and I don’t think there’s anything that I would have done differently overall.

You’re now sitting on some pretty exciting boards — the State Library of NSW and the Data Science Education Institute. What drew you to this kind of work?

About a decade ago I had a mentor who suggested board roles might be a good future path for me. I’ve always had that rolling around in the back of my head, but I hadn’t acted on it until this year. In February I decided to update my LinkedIn to say that I was open to board roles, and amazingly a couple non-profits got in touch. Both of them are really aligned to my values and the things I’m passionate about, so it’s perfect.

I met Dr. Linda McIver of ADSEI many years ago at YOW, and instantly she felt like a kindred spirit. Her goal is to help Aussie kids build critical thinking skills and data literacy through real projects working with real world data. She’s a one-woman operation, but she’s surrounded herself with a network of folks who can help promote and support what she’s doing.

The other one is the Foundation board of the State Library of NSW, one of the oldest cultural institutions in our city. The Library exists to preserve and to share the entire history of Australia, to educate and inspire, and to knit us together as a society. They hosted a fantastic talk about that topic just this month. This is all near and dear to my heart, and it’s a way that I can feel I’m making the world a better place.

Incidentally, both institutions accept charitable donations! Please reach out if you need more info on either of them.

What was the process like joining a board? Any advice for someone keen to do the same?

Well, both of these roles are unpaid, so the process is very different from a paid board role. ADSEI was very simple and took less than a fortnight, with Dr. McIver reaching out and having a call with me to tell me more about the org and what she needs from the board. Then I joined a call with the other board members to introduce myself, and they held a quick vote via text to confirm my appointment.

The Library Foundation board was a more formal process, where over a period of months I met with a current board member, the Board Chair, State Librarian, and Foundation Director to talk about what the board does and how I could contribute. I had to write a Board CV, which is very different from a normal one. The interviewers put forward a recommendation to the Library Council governance board, who approved me. I even had to have new headshots done to go into their annual report!

I’m still not sure if I want to go for paid roles, but the tried-and-tested approach for getting those is to do the AICD Directorship course. It’s expensive, but I’ve spoken to many folks who’ve done it and they all feel like it was worth it. There are occasionally scholarship opportunities for it, and I’m keeping my eyes open for those. They also do a shorter course in directorship for non-profits, which I will likely do at some point later this year.

If you’re thinking of taking on a volunteer position, I highly suggest you check out Volunteer website. Once you put in your location, you can filter the “type of work” to “Governance, Boards, and Committees.” I’ve seen a couple interesting non-profit opportunities come up on there. Beyond that, do what I did and change your LinkedIn profile to say you’re open to board roles. You might get lucky!

Was there ever a 'road not taken' in your career that you wonder about?

A couple. The big one is that I didn’t actually do a CS degree. In the 90’s I fell in love with computers and the Web, but that didn’t seem to be what the Computing department at my uni focused on. None of the people who did those courses looked like me, and I convinced myself that I wasn’t interested in learning about algorithms and data structures. In reality, I was just scared that I wouldn’t feel welcome, and wouldn’t be smart enough. Instead I did Communications, taught myself HTML, and spent all four years building websites as a side hustle. My first job out of college was as a web developer. I still wonder what my career trajectory would have looked like if I’d been braver back in uni.

You’ve been blogging since the early 2000s — a true OG! What has writing publicly taught you about tech, yourself, or connecting with others?

Lately, it’s taught me about blocking LLM content scrapers. Grrrrr. But truly, it’s taught me a lot about how stubborn I am! So many blogs from that age are just gone. We used to think that once you put something out on the Internet, it was there forever. That’s just not the case. It takes a lot of work to keep a site online over many years.

For the past four months, I’ve spent about an hour (every single day!) going back through my archives and cleaning up broken links. Link rot is so depressing. I’ve imported all my content from the walled gardens of Instagram, Twitter, and Facebook and deleted it from those sites. I really vibe with the Indieweb folks. I’ve made a conscious effort to post more on my own platform, and I use Echofeed to syndicate it out to Mastodon and Bluesky. It’s hard though, knowing that unless something is on Facebook, most of my friends and family won’t see it.

Beyond that, it’s also shown me how much I’ve grown as a person. Looking back over old entries, there have been things that I wish I hadn’t said. I’ve shared opinions that I don’t hold anymore, or said unkind things that I would never say now. I’ve had to decide how to handle those, whether to own my own words or disavow them. I guess you could get the same result with a private journal, but I think there is value in wrestling with these things publicly. I’ve made some great friends and connections through the site, and I love having a record of my life over the past 25 years.

Any podcast you are currently listening to, or a book you are reading?

After many years of only reading work-related books, I’ve been really enjoying catching upon fiction! I copied this list of the 100 best books of the 21st century into my phone Notes last year, and I’ve managed to get through over a dozen so far.

I’ve also finished off some fun-but-less-prestigious stuff, like the first few Murder bot novellas. I also revived my Goodreads account and I’ve been bookmarking interesting recommendations from my friends. My favourite so far this year has probably been Station Eleven, which is about the aftermath of a pandemic… but is really about a lot more too.

What is your favourite tool or resource, and why?

Can a community be a resource? I’ll call out Sydney Technology Leaders, the meetup group I’ve been affiliated with for the past 8 years. While I’ve stepped back from the bulk of organising duties, we have a Slack community where people often share articles, debate trendy topics (ugh, AI again!), and post job opportunities. If I ever decide to go back to a full-time job, that’s the first place I’d announce it.
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More concretely, let me tell you how much I love my sewing machine. 😍 When I started out sewing 20+ years ago, I had a very simple machine that did the basics and worked just fine. Finally, a few years back I decided to splurge and upgrade on one with all the bells and whistles. I love it! It makes sewing such a pleasure. I’ve made clothes for myself and my husband, gifts for my friends and family, even a couple AWS dresses (that I later turned into bucket hats for a charity fundraiser). Next up will be a pair of ridiculous pajama pants for myself, made with some special digitally printed fabric. When the zombie apocalypse comes, you’re going to need me and my sewing machine in your walled commune. 😛

What’s something on your “life bucket list” now that you’re no longer in the full-time hustle? Travel, hobbies, learning something completely new?

I’ve got so many! The one I’m most excited about right now is weaving. I’ve given talks in the past where I spoke about how the Jacquard loom with its punchcard system was an early form of programming, and how it inspired Charles Babbage’s Analytical Engine. I’ve never had the time or energy to give it a go myself though. But 2025 is my year of weaving! I did a class in February where I learned to use a massive floor loom to weave a rug over the course of a day (plus several more days of finishing the edges). That inspired me to join the Hand Weavers & Spinners Guild of NSW, and next month I’ll be doing a class with them on weaving with a Rigid Heddle Loom. No, I don’t have any idea what that actually is… but doesn’t it sound fascinating?!

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You might also enjoy these interviews:

From Designer to Product Leader: A Career Chat With Jeni Oye

From Engineering to VP of Product: A Career Chat With James Hill

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