What joining a startup taught this 40 year-old about the necessity of risk

Sarah Dlin
The Better Story
Published in
6 min readJun 7, 2017

I’ve gladly embraced losing my identity.

I’ve gladly replaced who I was — or thought I was — with anxiety, apprehension, uncertainty.

Well, I’ve been glad about it on most days over the last 9ish months.

See, a combination of borrowed courage and luck have shifted me out of my very, very, very comfortable Comfort Zone and landed me in a position where I am now working for a SaaS startup. A decidedly lean SaaS startup.

At 40 years old. 😬

Let’s be honest, starting a new career midlife is not a novel concept.

When the average American (which I am not, but that’s what I had available to me) stays in a job for just shy of 5 years, you know the days of hanging on to your job to collect ye olde gold watch are behind us.

The last time I saw an employee receive a gold watch for long-term service, it was 1994 and it was attached to a ticking time bomb. (Which is perhaps appropriate.)

Aaah, only Keanu could have saved Sandy B et al from disgruntled retiree, Dennis Hopper

Switching careers has become a sort of rite of passage. First you have to do the thing you thought you were supposed to do. And then you get to look for the thing you actually want to do.

So why did I decide to switch careers?

Job ennui (or a plateau in job satisfaction due to lack of opportunity or excitement) is a concept that floats around the career counseling world. And, if you haven’t already noticed, you’ll not have to look too far to see symptoms.

For me, I entered job ennui 8 years ago. Almost daily I complained of needing more. More challenge. More opportunity. More fulfillment. I bored myself talking about it. And, by the time I finally left my career as a nurse, my family was well over the convo too.

So when I moved to a new city, thanks to my partner’s career, and couldn’t find a job in my field that would meet my need for a new challenge — a greater purpose — I took the opportunity to learn a little bit about myself.

I gave myself about a year to figure things out. In that time, I tried my hardest to search my soul but honestly how does that even work? I invested over $2000 in career counseling advice (on a single income this was a HUGE investment). And what I wound up with was a stronger sense of what I’d already known about myself: that I liked working with people, that I liked to learn.

But I still didn’t know where I should focus my strengths.

So when the opportunity to join a new startup surfaced, all I could think of was that damn Tina Fey quote — you know, the one she said about hosting the Golden Globes:

“Say Yes, and you’ll figure it out afterwards.” Tina Fey

From what I knew about startups (hey, I’ve watched The Social Network 😏) I felt I was in for, at a minimum, a welcomed work culture shift.

This is the quintessential startup culture, right?

Creativity, innovation, ambition — all the things I found my previous role sorely lacking make up the culture of a startup, right?

After the romantic fairy dust of working for a tech startup wore off I began to sweat.

What the hell did I know about working in tech? A little reading led me to conclude this: although startups are where talented, ambitious, innovative and curious creatives go to grow, the startup culture embraces — dare I say, needs — people who are flexible, customer-centric and resourceful. People like yours truly.

Except the list of startup needs doesn’t stop there. Every business needs flexible, customer-centric, resourceful people.

Startups need more than that.

Now let me preface what follows like so: I like stability. I like knowing where my paycheque is coming from and how much it will be. I like prescription and vision care coverage. I like getting my teeth cleaned by a hygienist twice a year. I like unions.

I like comfort.

But that’s exactly what brought me to the proverbial crossroads I was facing. I needed risk. I needed discomfort. I needed to pivot a full 180 degrees. I needed to be part of this crazy startup world for the same reason we do really ambitious things like going to the moon: not because it’s easy but because it’s hard.

So, with almost 9 months of startuping (sure, it’s a word) under my belt (hold your applause) and the (ahem) opportunity to reflect on my time at Airstory, I’ve come to see that maybe the fear born of not knowing, maybe feeling like an imposter and maybe realizing there’s so much growth ahead 😩 — maybe those are all signposts that I’m heading down a path worth pursuing. Maybe.

Here is the first of 4 lessons I’ve learned after 9 months of working in a lean startup.

“The biggest risk is not taking any risk” — Mark Zuckerberg

Fifteen years as a registered nurse reinforced my proclivity to be risk-averse. For me, risk-taking is synonymous with recklessness. Certainty is safe and rational.

There’s a reason I never went into business for myself. I’m too safe. I’ve never honed that part of my personality that’s been ok with uncertainty, that likes to take risks. I like being able to predict what I will be doing six months from now and I’ve always felt this is best accomplished by conventional means (i.e., the reason I became a nurse, the reason I completed a master’s degree in nursing even when I was soooo over the whole thing).

Working for a startup, you gotta give up on the idea of stability — this much I knew.

But what I didn’t know and have since come to realize is this: a risk is necessary to creation. Being part of a startup means you pivot when the solution doesn’t address the need as expected. The risk allows Airstory to keep innovating. And that same risk also helps me keep innovating on, well, me.

It’s about “think[ing] a little and then do[ing] a lot.” Dharmesh Shah

I’ve come to learn that lean startups need to risk while iteratively designing a solution to a real, customer-driven problem guided by this thought:

Is this the right solution for our users’ problem?

It’s not entirely about well-crafted business strategies or the traditional product development process.

Being part of a lean startup means you identify a real problem and talk to those that the problem impacts and then create a product to address that problem. There’s no elaborate business plan or endless, fruitless meetings with stakeholders wherein benefits are carefully weighed against the risks. There is experimentation and real-time product development that address the problem for the target customer — in spite of the potential risk.

When I want to scream “No, let’s implement EVERY user’s request because we’re just starting and we need all the business we can get!” our fearless (read: risk-taking) leader says calmly, “No. It wasn’t for them.”

I’ve been told more than once that Airstory is in the business of answering a real problem for a specific group of people. We’ve listened to what our ideal user wants and now we need to pivot until we get it right for those people.

Airstory will not be for everyone.

To me, that’s risky.

In my safe, stable, certain world, I would cater to almost every Airstory user because that would ensure Airstory makes money. Or so my non-startup mind thinks.

It’s scary to innovate. It’s scary to take risks. But the payoff is this: I get to be part of a solution for a real problem. And at the same time, I get to explore parts of who I am that I never would’ve had I continued on in my safe career as an RN.

Join me next week to read more about this neophyte’s Startup lessons and, in the interim, tell me about your start in a Startup 😊

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