Is a Startup the Right Move for You?

Kanav Bhama (Business Operations, Dovetail), Jess Rogers (Strategy and Operations Manager, Snap Send Solve), Ellen Dinsmoor (Head of Operations, Vow), Will Dennis (APAC Commercial Finance Director, Afterpay), Rhiannon White (Chief Product Officer, Vend), Rebecca Evans (Marketing Manager, Sonder)
Kanav Bhama (Business Operations, Dovetail)

These were the questions I asked myself prior to taking the plunge from the corporate to start-up space: 

  • Could I possibly have a bigger impact working with smaller businesses?
  • What is my risk tolerance at this stage of my career? 
  • Do I strive in structured and stable environments, or am I comfortable with ambiguity and constant change? 

Jess Rogers (Strategy and Operations Manager, Snap Send Solve)

A lot of thinking I did before deciding to pursue a start-up career centred on the kind of impact I wanted to have in my career. I don’t have questions to ask, exactly, but a few resources that helped me decide on start-ups were:

  • Wait But Why has written a really brilliant article about How to Pick a Career. It's really clever and poignant and worth taking the time to read. It shares practical exercises and reflects on the role that people in our lives and other influences play when we define success. 
  • 80,000 Hours (the length of the average career) researches what issues are worthwhile working on if you want to have a career with impact i.e. what are the most pressing problems facing the world in our lifetimes. I recommend reading the Key Ideas section to start because it sums up their philosophy really well and provides a helpful framework for finding careers where you can have a tangible impact. It's worth printing out because it's quite long. 


I found these really helpful for frameworks about how to think about career, even if I didn't agree with everything they said or or had ambitions that exactly aligned with their suggestions.  

80,000 Hours has also just launched a course on planning a high impact career, which could be an interesting way to explore. It also runs a curated job board of high-impact jobs, which can be helpful for seeing the types of roles that exist and get a feel for what appeals. 

I found all these resources helpful to start my thinking and go into conversations with contacts and mentors with an idea of what was important to me, even if I didn't know exactly what job I wanted. There's definitely no right way. Start exploring, take your time and see what comes your way! 

Ellen Dinsmoor (Head of Operations, Vow)

Ask yourself these questions:

  1. What is your tolerance for frequent change? 
  2. Do you have any extenuating family or friend circumstances which should take higher priority in your life right now? If you’re taking care of an older family member, prioritise that, not the demanding lifestyle of an early stage company.

Lee Lubner

Will Dennis (APAC Commercial Finance Director, Afterpay)

Assessing one’s own risk tolerance to join a start-up is an important threshold question, which could be influenced by factors such as family and lifestyle financial commitments. 

Getting clear on your own motivations for wanting to join a start-up can also be informative. For example, motivation driven solely by potential financial gain could lead to a poorer experience than motivation driven by other factors such as alignment with the start-ups purpose and mission.

Rebecca Evans (Marketing Manager, Sonder)

Ways of working: To thrive in a start-up, it'll be important to be OK with ambiguity. Today's burning fire will be a distant memory tomorrow. My advice there is "done is better than perfect". That motto has to change when a business grows, but it's something that's always worked for me. This ambiguous nature of a work-place isn't for everyone. If you're process driven or you like to know where your job starts and ends then maybe a later stage start-up culture might be better for you.

Rhiannon White (Chief Product Officer, Vend)

I was given some great advice a few years ago by a serial founder here. He advised that you think deeply about the size of organization you thrive in - for example under 50 people? 50-100? 500+? And then also think about the stage - pre-seed? Seed? Series A,B,C? For me, I know I prefer post-money but pre-liquidity event (so usually Series B or later) and post-100 employees but sub-1000. Reflect on the times you’ve most enjoyed work and if there were structural elements that you can identify.

Hannah Neep has written an amazing article on this topic here

What have we missed? Please hit 'Contribute to the Guide' to give your perspective and help others into their first role.

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