Balancing the Grind with Jordan Hughes, Design Lead at UpGuard

Jordan Hughes is a Sydney-based multidisciplinary designer and currently the Design Lead at UpGuard, one of the world’s fastest-growing cybersecurity SaaS platforms.

1) To kick things off, could you tell us a little about your career background and current role?

Hey, I’m Jordan. I’m a multidisciplinary designer based in Sydney.

I’m currently Design Lead at UpGuard, one of the world’s fastest-growing cybersecurity SaaS platforms, with global customers including NASA and the New York Stock Exchange.

Prior, I was the second employee at Spaceship, an Aussie financial tech startup, where I was the Operations Manager and part-time designer. Spaceship was the fastest-growing new entrant in the world, growing to $100m in assets and a 50,000+ waitlist before we had even launched. It was an interesting experience and we raised $40m+ in venture capital.

Outside of work, I spend my nights working on freelance or side projects; notably Good Books, Breakout Careers, and another project in the works.

I don’t have a background in design and have only really considered it my “career” in the last 12-months when I decided it was my next focus. I studied Management and Finance at UTS.

2) What does a day in the life look like for you? Can you take us through a recent workday?

I love habits and routine. It’s a bit boring, but I work best when I can structure out my days for periods of uninterrupted deep work. I work from home most days which is perfect for me.

I try to get up at 6am and I’ll usually take this first hour to ease into work and listen to an audiobook or podcast. I’ll make a batch of coffee and breakfast and try to be awake and at my desk by 7am.

I’ll usually use this time to focus on side projects. Occasionally, I’ll take on freelance work or use this time to master a new skill. This is my most productive time to work.

At 8:30am I’ll check in with the team at UpGuard. They work in sprint cycles so I’ll work on designing upcoming features. I also work closely with their Head of Growth on marketing projects (website, emails, sales collateral etc.) outside of this.

I try to reserve my morning to tackle my no. 1 priority for the day or the most difficult problem. Once I’ve made progress on that, the rest of the day is a lot easier. I’ll then spend my afternoon working on other priorities, taking a 15-minute break if I’m feeling unfocused around 3pm.

At around 5pm, I’ll close Slack and my notifications are off for the rest of the night. I’ll try and get some exercise or go for a walk at this point to switch off. My girlfriend and I love to cook and go a bit overboard most weeknights which ties me up till 7:30pm.

I try not to go back to my desk at this point. Sometimes I will if I have a deadline for a freelance project, but it’s not going to be my best work. Usually, I’ll just grab my Macbook and sit on the couch to do some less-intensive design work, reading or admin stuff. Shallow work that I try not to waste focused time on. Or I’ll just relax.

On most weekend mornings, I’ll reserve until around 10am for freelance and side projects. I try and maintain the same routine and get real work done here. I don’t see it work as I’m usually working on something I’m passionate about. If I’m not feeling it, I’ll just take the day off work.

3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?

I’m very fortunate to work with the team at UpGuard—they are very supportive of autonomous and remote work. I work from home most days which is perfect for me, and we have people all around the world.

I really believe you can achieve a usual workday’s output in 4 hours if you can just focus and cut out meetings and distractions. I’d like to think more companies are waking up to this.

There are definitely benefits of working together in a space when it’s the right space. But loud colleagues, office politics and Slack are not conducive to good work.

4) What does work-life balance mean to you and how do you work to achieve that goal?

I think the definition of work-life balance differs with everyone. Some people have different internal drivers and goals.

I’m pretty internally driven and restless, so my ideal work-life balance is having more time to spend on things I want to work on and on personal projects. I’m starting to value this more every day and learning to switch off when it’s time to switch off.

Setting boundaries with work-life balance was something I was seriously struggling with a few years ago—I was working very long hours in a toxic environment. I’m at a place now where I’m pretty happy with my balance.

I still work long hours sometimes, but when I do it’s because I want to work towards my own goals and not at the detriment of my health or relationships. Separating work and life is really about control and discipline and I had to learn that.

If your work-life balance isn’t what you want it to be, it’s 100% your responsibility to fix it.

If your current job is affecting your quality of life or making you work overtime, you should quit and find a better job. Immediately. It’s not worth it in the long run and you’ll figure it out. No work is as important as people make it out to be.

5) What do you think are some of the best habits or routines that you’ve developed over the years to help you achieve success in your life?

A real tipping point for me was reading Deep Work by Cal Newport back in 2017. It’s one book I try and re-read once a year and it really opened my eyes to how distracted I am.

I’ve developed this into a habit by structuring my day for periods of time to focus. Cal calls this the “superpower of the 21st century” and it’s probably the one habit that’s made the biggest impact on me.

Working on one thing at a time and working on it well is the key to getting into a flow state and getting things done. I ruthlessly block out everything else, which goes on a to-do list in Notion so I can clear it out of my mind completely.

Pairing this with a consistent routine is pure compounding magic. I’ve seen it pay dividends in my own work and progress in just a few years. You can pick up skills faster and operate at a higher level than people with 10+ years more experience.

Outside of work, getting 8 hours of sleep and eating a super healthy diet every day has a huge impact on my energy and focus. This doesn’t mean I don’t drink or eat out – I’ll have a glass of wine most nights and anyone who tells you that’s bad is a duffer.

There have been many habits I’ve tried to work into my routine that haven’t stuck. I’ve tried meditating daily for weeks at a time, but it’s not for me and that’s totally fine as well.

6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?

Few books have had as much of an impact on my life than Cal Newport’s Deep Work or James Clear’s Atomic Habits — focus and habitual behaviour are a powerful force multiplier. I’ve listed a few other great books on habits and productivity here.

On work, David Epstein’s Range is a great read on the future of your work in a generalised world and why you’re probably doing it wrong. Bill Walsh’s The Score Takes Care of Itself is a memoir and philosophy for work and life that really resonated with me (and I don’t even watch football).

On life, Ryan Holiday’s The Obstacle is the Way was my first introduction to Stoicism and I recommend it to anyone trying to find balance. And Jonathan Safran Foer’s Eating Animals is an important book I think everyone should read.

7) What is the number one thing you do to make sure you get the most out of your day?

I’ll carve out 1-2 hours before my workday starts to focus on personal projects every morning. I’ve found this is by far my most productive time when my energy and mind are sharpest. It’s quiet and there are no distractions. I will very rarely miss a day now.

I’ll use this time to work on freelance things or side projects, whatever is most pressing. It doesn’t sound like much, but if I do this every day it adds up to 5-10 hours per week of focused work.

It’s such a habit now that I don’t think about it and it allows me to actually get (real) work done instead of just shallow stuff. If my workday is clogged with meetings or less important tasks, I’ve at least got that win in before my day really starts.

8) If you could read an interview about work-life balance by anyone, who would that be?

I’d love to chat with Sam Altman. He’s accomplished more in a short career than most people do in several lifetimes. His frameworks and writing on personal risk, balance and compounding your career have had a huge impact on me.

9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?

Relax: no one actually knows what they’re doing. Taking things too seriously and focusing on one specialised career path (usually because of a uni degree) is a huge trap for people in their twenties.

I think the most important thing you can do instead is to learn a wide discipline of skills, build good habits, automate your finances, and learn to focus. Compound interest is a good metaphor here.

If you can implement these pillars early in your career and improve a little every day, you’ll be miles ahead in a few years. The more you compound, the more leverage and freedom you’ll have to dictate the work-life balance that you want.

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