This chick walking a tightrope in high heels across looming sharks below is a pretty accurate representation of how I’ve felt at certain points over the last several years.

We all know that if you’re going to be an entrepreneur,
you have to be tolerant of risk at some level.

And for some of us, it’s harder than others to take those chances.

(Personally, I was a bit of a wild child. I went skydiving + bungee jumping + scuba-diving {with sharks} all before the age of 19 … So I’m okay with a certain level of risk.) 😉

But what I want to share with you today is how the path towards being an entrepreneur is certainly full of risk, and isn’t necessarily linear.

Slow growth is ok.


I graduated from college during the heart of the recession, in 2008. Struggling to find work and survive, I took on a series of jobs I hated – but that I now realize were absolutely essential to my development as an entrepreneur.

With my first job, I would wake up and cry every day before I went into the office.
My second job brought on waves of anxiety and panicked breathing.

Perhaps because I was so unhappy with my jobs, I placed a lot of importance on my big dream to help women in India. I was super passionate, completely unskilled, and totally in denial about that. 

So, I quit my job when I was 25 to start W+S and moved to India for a few months.
I rented a space. It was just me in basically a modest-sized flat.

Then I met one woman, who moved in + started knitting.
Then another.
I hired a manager to run the operation. 

Eventually, having kicked off the venture, I went back to the US.
I woke up to have Skype calls at 3 AM, and worked from morning until night, realizing I was still in my pajamas at 7 PM.

There was no work/life balance. And I was running out of money.
hen the manager in India quit – her commute was too long. 

Looking back, I don’t even know how we continued.
I was super eager to build WORK+SHELTER, but I was broke.
I didn’t have enough of a foundation. 

It was then that I got a call from a recruiter at Google … Thank god. I got the job, and they eventually told me they had hired me because of my “enthusiasm.” ( 😀 !!!) 

So began the double life I led for years.
At that time, as WORK+SHELTER grew, the amount of risk that felt tolerable for me was the amount of my paycheck. 

 What if we screw up all of our orders this month at WORK+SHELTER and have to order the fabric again – how much will that be? If we don’t get enough business next month, will we be ok?
Yes, because I can send my paycheck to India. Which I did. Multiple times.

That was in 2011. It took until 2015 for the timing to finally be RIGHT.

WORK+SHELTER had been open for almost 3 years at that point. The corporation I worked for in the US restructured and suddenly I was out of a job.
Immediately, I knew it was time to seize the opportunity.
I had severance, got paid out on all my vacation. I had savings. It was finally time to make the move again.

So, I quit my day job to focus on WORK+SHELTER full-time. And this time, it worked!


Take gradually increasing increments of risk. There is no shame in growing slow.

Before you the bet the house…

What do I know about this industry?
Do I know more than other people?
What do I know that others don’t?
Have I done my groundwork?

I was an idiot. I didn’t know anything about the fashion world, or manufacturing, or garment construction. Thank god I had a day job.

Do I have the necessary resources to survive, while this idea takes longer than I ever thought possible to get it off the ground?

If the answer is not already YES, get it there first.

How can I mitigate my risk?
How do I limit the amount of money I’m spending?
How do I test my model without expending too much?

I did this. We started small – didn’t even buy machines because of the infrastructure costs. We started with knitting.

There are consequences if you don’t play your risk right. 

I know someone who spent two years trying to get a new business off the ground. He purchased material for production before he even had a final pattern ready for his order.

He just quit his business. It didn’t even get off the ground.

Because his interest in running the organization was more than his ability to actually DO IT.

And that’s true for most of us. Beware of THE GAP.
You know, the one that Ira Glass refers to. This one:

It is the gap between your skills and your dream. The gap that doesn’t mean you shouldn’t move forward.

When you have a dream that you care enough about, you don’t really have a choice but to pursue it.

As the saying goes…

– John Shedd

So just don’t overdo it at first, given that you have so much to learn.
Yes, you GO TO SEA, but before you do – make sure you’ve done as much preparation as you possibly can.

Now go throw on those high heels (but tbh I mostly wear motorcycle boots because they make me feel tough…), jump on that tightrope, + strut right on past those sharks!

Or, just go scuba-diving with them. Highly recommended.


xo, Theresa


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