When someone tells you they have a side hustle, there’s often an assumption made that they’re putting less energy or focus towards their main job.

On the contrary, something we’ve witnessed in the Earlywork community is people leveraging their side hustles not just to land new roles, but to polish the skills they need for their day-to-day work.

We’ve previously covered the most important factors for Why You Should Start A Side-Hustle, but in this week’s piece, we wanted to dive deeper on a real-world story from the Earlywork community of how a side hustle translates to tangible career growth.

That’s why we sat down with Vihan Ramanayake, APM at Simply Wall St and co-founder of the UNSW Sandbox Society, to talk about his experience in leveraging his side-hustle to build a career in startups.

Here are the insights he gained:

It was November 2020 and I had just finished my fourth year of university. It suddenly dawned on me that I had less than a year left in my university journey.

University failed to set me up for the practical skills I need in my startup role.

But there was one thing I did on campus that made a huge difference to my career.

A friend and I were both studying tech degrees and we experienced firsthand the lack of opportunities to work on real-world problems and build practical skills whilst at university.

We decided to co-found UNSW Sandbox Society, a student society that aims to bridge the gap between university and the workforce by simulating real-life problems in a sandbox environment.

In our first year of operation we:

• Grew the team from 0 to 27 members
• Acquired 450 student members
• Established a flagship program with over 40 students participating in our first intake
• Received funding from the university student body

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Starting a side hustle is one of the most powerful ways to set yourself apart when it comes time to land a job in startups.

But beyond the job offer, it gives you a critical head start on learning how to drive projects independently in a crazy, ambiguous environment.

Here’s how to position your side hustle to land a role, and how to leverage it to get ahead in your startup career:

Landing a Role 💼

Let’s first ask the question: why side hustles?

Aren't there better ways to break into startups like working in a reputable and prestigious firm?

First off, many successful startups and companies are spin-offs of what were once side hustles.

• Craigslist started off as an email list to update people on events
• HubSpot started off as a blog about entrepreneurship
• Twitch (originally Justin.tv) was a website where Justin Kan live-streamed his life

But even if you’re not setting out to go full-time on your side hustle, going from zero to one and starting a side hustle comes with valuable challenges.

You get comfortable tackling ambiguity, and it requires a great deal of proactivity and resourcefulness, which are all skills startups eagerly look for when hiring.

Beyond the raw skills, side hustles make you stand out from the crowd because no two side hustles are identical.

Two candidates can have the exact same marks and experience, but what really makes a difference is what you've done outside the classroom and work.

A side hustle is what makes your story unique. It gives interviewers something novel to ask you about and remember you for.

Thriving in your Role ⭐️

Working on a side hustle helped me develop two critical skills that accelerated my career in startups:

1. The ability to navigate ambiguity
2. Resourcefulness

If you're looking to break into startups and you already have a side hustle, understanding the importance of these skills will allow you to tell a much more compelling story to startup employers.

If you've built a side hustle and managed to land a role in startups, understanding how to leverage these skills to create impact in your role will accelerate your career in startups.

Navigating Ambiguity 🤔

Startups are figuring out the best way to do things, which means there's no step-by-step manual to follow.

This is in stark contrast to corporates, who have established (although often inefficient) processes in place to get things done.

Therefore, startups value people who are willing to try things, learn and fail quickly, in order to figure out how to drive better outcomes. That’s exactly what a side hustle sets you up to do.

Starting a side hustle is not the only way to learn how to navigate ambiguity, but it sure as hell is the fastest way to become an expert at dealing with uncertainty.

In the early days of starting UNSW Sandbox Society, we knew we wanted to create a program that gave students a risk-free environment (hence the name Sandbox) to build practical skills in fields such as design, product management and engineering.

Unfortunately, no one had created a similar type of program before, so we had no idea how to structure it.

I ended up having countless conversations with academics, employers in the tech industry and students to gain important insights that formed pieces of the puzzle we were trying to solve.

From this experience, I learnt that you're not expected to know all the answers. Don't face ambiguity alone. Speak to people who can guide you in the right direction.

Equip yourself with lightbulbs, in the form of insights from these conversations, that will help you navigate through the dark.

This learning is particularly relevant in my current role as a Product Manager.

I was recently tasked with redesigning our onboarding experience for new users. Our product, a stock market analysis platform for retail investors, is a fairly new product category, so there's no clear formula for onboarding users.

If you're building a social network, for example, there are proven steps that work when onboarding users: setting up an account, adding friends etc.

To break through the ambiguity, my side-hustle instinct was to speak to users directly to figure out their pain points, so we could design an onboarding experience that worked for our product.

Resourcefulness 🔎

Resourcefulness is the ability to make the most of what you have. Someone who starts a fire with sticks is said to be resourceful.

Startups, by nature, are resource-constrained all the time.

Financial resources, human resources, and time don't come in abundance, so you need to become an expert at finding creative ways around problems.

Starting a side hustle equips you with a lean mindset. Whether starting something with a team or riding solo, you become an expert at maximising the output of your circumstances.

At UNSW Sandbox Society, we had to build a recruitment system to start hiring people who could help us run and grow the student society.

We were considering using a recruitment tool to help us with this, but we realised we could achieve the same outcome using Google Forms and Google Sheets, which we were already familiar with.

This meant we didn't need to spend time learning how to use new software, which allowed us to move fast and be among the first societies to start recruiting students for that time period.

Before you go looking externally to solve a problem you're facing (e.g. using a new software), think about how you can achieve the desired outcome using what you already have.

If you can build a reputation for getting the job done in the quickest and cheapest way, you will set yourself up for success in a startup environment, and that mindset has been a huge help at Simply Wall St.

A big challenge we recently faced was interviewing users who registered for our product and didn't return back to our app.

These users are notoriously harder to reach because they aren't sold on the value of the product, so they're not willing to give you time to interview them.

One option to solve this problem was to pay for user research tools that give you access to a pool of participants to interview.

Instead, I decided to use what contact pathways we already had with them. I leveraged our email marketing platform to set up a custom audience that targeted these users and built a recurring recruitment campaign, which allowed us to have ongoing access to a larger pool of users to interview.

In Summary 💪

I would argue you'll have more success breaking into startups if you focus your energy on building a side project beyond just your day job because:

1. They make you stand out when job searching and give you an edge in interviews
2. You gain the ability to navigate through ambiguity and adapt to change rapidly
3. In a resource-poor environment, you are forced to become more resourceful - an invaluable skill in a startup