Growth, Impact, Joy: Should I Join a Startup?

Two questions to ask yourself

When I’m building a team at a startup, I’ll spend a lot of time talking to candidates and answering questions. One topic that comes up a lot is why join a startup versus a big company, and for good reason: jobs at larger, more established businesses are perceived to be safer opportunities.

My approach to this topic is to consider the two questions that the candidates are asking themselves:

  1. Should I join a startup… or a big company?
  2. If I do decide to join a startup, why should I join this one?

… and to answer them in turn. If you're thinking about working for a startup, you will be more successful if you are ready for the startup world in general. That’s question one. If you’re ready, then I’ll tell you why this startup is a good one, and a good fit for you. That’s question two.

This post is about the first question: your decision to jump into the startup world.

(Obviously: startup vs big company is a grossly-simplified dichotomy. My definition of a startup is a company that’s trying to bring something new to the world. That’s different to a company that’s simply small, but in reality they end up sharing a lot of characteristics. And of course, every company is different. That’s why you should consider if this startup is the one for you.)

Thank you, Twitter!

I’ve made the decision between startups and bigger companies a few times, most recently in 2016 when I left a 60,000+ retail giant to co-found Residently. And I’d recently dug out the pros/cons list that I wrote when making that decision, so I had some data points of my own. Even so, I thought it would be great to get some opinions from you lovely Twitter people - so thank you to all who replied.

I’ve grouped your awesome responses into three areas - Growth, Impact and Joy.


One of the reasons I feel comfortable hiring people into a startup team is that I am confident in the growth opportunity that we can offer them. Everybody leaves more qualified and more employable than when they joined, regardless of how long we end up getting to work together.

On Twitter, you mentioned the flexibility in roles that working in a startup can bring. Startup life means wearing lots of different hats. For a developer that can mean working across the whole stack — great for a first role in tech, great for learning a new stack, great for being able to deliver value end-to-end and great for being useful and helpful.

This flexibility is not only on the tech stack. It’s totally possible to join a startup as a developer and move to doing a different role, such as product or engineering management. And it’s not only for developers - you can (and will!) find yourself working across marketing, sales, product and operations. These sorts of movements are often way more difficult to achieve at a bigger company.

And as someone who loves to learn and loves to help, I find startups can be a great place to do this.

Another thing that a few of you mentioned around growth was that startups can be more open-minded and respectful in their recruitment practices. If you’re looking for a big change, they can be a good place to start. A friend of mine did this: she left a career in HR at a big bank and joined a startup as office manager (a job she’d never done before), and gained experience worked on hiring, strategy, events, projects — a real tour of new career options.


I like this quote from Anne Boden, founder of Starling, on why she didn’t launch a challenger bank within the traditional retail banking sector that she knows well:

“I came from that world… if I thought I was going to be able to create that I would have done,” says Boden, pointing to the burden of legacy infrastructure. “It’s very difficult to replicate the energy and technology of a startup.” Sifted: Inside Anne Boden’s Starling

In addition to doing a lot of good for your own career, startups are a place to change the world — and because there’s less to lose, there is less to risk. That freedom is not easily replicable in a larger company, where there is more on the line and the stakes are so much higher. It’s right for companies who have a valuable asset - a brand, a loan book, a user base - to be cautious about it, but that caution also lowers speed of innovation.

Startups are also a place where individuals can enjoy autonomy, input on decision making (whether tech stack, UX or process) and the freedom to try things out.

This feels similar to Stephen Covey in ‘The Seven Habits of Highly Effective People’ where he talks about the Circle of Concern and the Circle of Influence. I’ve found startups to be an effective place to align the two.

Speed is important to you startup types, too. It’s hard to stay motivated and urgent when you’re watching projects take months or years to finish — or even worse, watching them get cancelled halfway.


The last theme, and perhaps my favourite, is joy. The simple joy of stuff working.

When I looked back at my startup pros/cons list that I wrote in 2016, one pro was being able to receive post and deliveries to the office. It sounds silly, but in my previous role it wasn’t possible to get a delivery. In the age of ecommerce, this was maddening!

At another role, my daily happiness was seriously wrecked by IT stuff. You’ll have seen people in big companies subconsciously and frantically jiggle their mouse every time the screensaver comes on: this is because laptops are set to auto lock after really short amounts of time, and sometimes they won’t unlock again. You can lose hours every day to these kinds of problems.

After three and a half years in startup land, I’d forgotten about this stuff. But it exists and it chips away.

There is a simple joy of stuff just working together.

The joy of the wifi actually working. And being able to put your phone on it.

The joy of not being emailed Excel documents when Google Sheets, you know, exists. And obviously, the joy of not touching Outlook.

The joy of being able to receive a package to the office.

The joy of being able to print something.

So it’s more than bureaucracy and policies: in short, there is a joy to be found when all the little things fit together nicely. And when they don’t, you can change them. This is a benefit of startup working that I think is frequently overlooked: your days go smoothly and you even forget that there’s a world in which they don’t. You can optimise for daily happiness.

I have loved working in big companies…

There are amazing personalities, minds, resources and audiences to work with and learn from at big companies. You can feel comfortable as hell, get paid great money and make a big impact on a lot of people. If you’ve spent your whole career at smaller companies and startups, I’d definitely recommend giving it a try.

… but if you haven’t considered working at a startup, you should!

What do you think?

What's your priority? Growth, Impact, Joy… or something else? You can share this post, follow me or join the conversation.