Redefining “Success” – The Biggest Shift in Moving to a Startup

Mistakes are the currency of growth, if you can embrace them

Eighteen months ago, I left a great job at a global financial institution to join a fintech startup just coming off its seed funding round. At the time, the company had just three employees who were designing our early products out of a small coworking space.

Like many professionals taking a less-trodden path, I found working to build a business and a brand both endlessly rewarding and incredibly challenging. However, as I look back, I never anticipated what would become the hardest part of this transition: redefining how I measured success and failure.

Like others who’ve spent the majority of their career at large, established companies, I was taught to see success as a metric for my personal performance. It was a binary calculus: Either you had delivered against your goals, or you hadn’t. You weren’t congratulated for getting it “almost” right. In fact, being perceived as satisfied that you hit “most” of your targets was a far worse sin than actually failing.

I was taught to see success as a metric for my personal performance.

At a junior level, I was promoted and my career flourished because I was able to complete challenging tasks, meet deadlines (some of them pretty unreasonable) and work with those who were viewed as “difficult.”

My identity and sense of accomplishment were tied to my belief that I was “successful” at my job—and that others viewed me the same way. Whether I realized it or not, I came to view “failure” as the exact opposite: a reflection of my own personal weaknesses; something to overcome simply by working harder, staying later and finding a way through.

It worked well for corporations—but not so well for startup life.

By definition, a startup is built from scratch and, more often than not, involves trying to create an entirely new way of approaching a problem with minimal resources. While an established company has the benefit of a large team, a substantial marketing budget, focus groups and a known brand (among other things), a startup often lacks those resources, or rarely has enough of them.

What startups do have is the freedom and agility to experiment, as well as the ability to learn and react quickly.

For me, this was not an easy transition. Having spent my career chasing success and avoiding failure, I suddenly struggled to shift my perspective. I needed to accept that, at a startup, you can’t fear failure, as it can be one the most valuable tools for gaining critical insights—into both the company and yourself.

For example, if you launch a new product, the metric for success at a large company may simply be, “Did enough people buy it?” At a startup, while your ultimate goal is obviously a profitable product, evaluating each step along the way can help determine success or failure.

When looking at your new product, ask yourself if you launched a working product on time. Then you succeeded by proving that you can scope, build and launch a product on a defined delivery schedule.

Did your marketing efforts result in new customers? Then you succeeded in demonstrating a tangible demand for your product and the value you offer.

But what if you didn’t see the volume of customers you targeted? Did you fail?

When failures happen, learn to harness them as fuel to help you and your company get to where you need to go.

From a purely binary point of view, yes, you failed. But in that failure, you also experienced successes that prove you’re on the right track. More importantly, if that failure provided crucial insights—for example ones that allowed you to improve the product, better understand the customer or change your pricing structure—then you’ve gained valuable information that will increase the chances of hitting that target in the next iteration.

While it was difficult for me to accept, that perceived failure ultimately becomes the catalyst of success.

For those moving into the startup space from large companies, the lesson can be difficult to accept: Failure isn’t always black or white, and it certainly shouldn’t be feared.

When failures happen, learn to harness them as fuel to help you and your company get to where you need to go.


Alastair is the general counsel at Kindur, an innovative fintech and insurtech platform offering digital wealth management, financial planning, asset management and insurance services to baby boomers approaching and in retirement. Prior to joining Kindur, Alastair served as chief of staff to Citigroup‘s general counsel and chief administrative officer for its 1,500+ global legal team.


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Spring I 2024



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