Are you willing to be challenged

By: Stella Orange

One of the hazards of running your own business is that we all have blind spots. Issues we can’t quite see clearly. Assumptions we’re making. Preconceived notions about what it will take to solve our problem that may not actually end up being right.

This is normal and human.

And one strategy to overcome this very normal, very human problem is to work with a mentor. Or as is the case here at Las Peregrinas, three of them. Having an outside perspective on the challenges and problems you want and need to solve makes all the difference. Because it lifts you out of your habitual ways of thinking, and challenges you to be creative, and think in fresh and generative new ways.

Years ago, when I was building my first business, I had created a successful and popular online membership program that created more than 100 customers and $100,000 of revenue in a single online email campaign. I was over the moon. And well aware that I had just achieved something many online businesses dream of – creating a leveraged program that paid me well, required very little of my active time, and served my customers well.

After that success, I wanted more. If I had 100 customers, how could I get to 300? 

I thought that was the problem I needed to solve.

But some of my advisors saw it differently.

“Stella, do you want 300 people in your membership, or do you want to be a new voice in copywriting?”

This question stopped me in my tracks. Because it had never occurred to me that I might need to sacrifice my beliefs to reach my goals.

Now, certainly this isn’t always the case. There are plenty of creative ways for a business owner to live her values, do her work in the world, and achieve her goals.

But in that situation, my advisors were right. And they saw something that I didn’t. To reach that goal of getting 300 people in my membership program, I was going to have to do a lot of things I really would not enjoy doing – email sales funnels, paid advertising, telesummits and speaking appearances that didn’t add real value to the world. And I’d need to “tone down” my message.

Thank the sweet baby cheeses I had advisors bold enough to ask me a powerful question, without assuming an answer.


Lately, I’ve noticed some of the questions we’ve been asking our clients:

Do you want five new private clients or to write a lead magnet?

Do you want to keep working for a client who does not respect your value, and does not pay you on time?

Do you want to develop a new product line for a new group of customers using a new sales process, or are you open to exploring other ways to increase your income while travelling less?

What matters most to you here? Why is that?

At the end of the day, there is no one right way to build a company. Sure, there are certain principles that apply to us all. But really, when you think about it, business is – or should be – a creative act. It’s our chance to express ourselves and bring value that is uniquely ours into the world, and ultimately, to change people’s lives for the better.

The trick is to be ruthless about want to create, before we leap into action. Not just ruthless, but conscious. It’s far too easy to get swept up in the “bigger, faster, cheaper” spectacle. But is that really what you are here for?

Our clients want to be the best at what they do – and they want to be known for the excellence that they bring to the task, whether that’s coaching, creating, consulting, or advising. The truth is, there is no conformist path to excellence. It takes knowing who you are – and who you are not – and then having the huevos to design your business and life around that, in every decision you make, from the teeny-tiny decisions to the biggest ones.

So when the time is ripe, may you have the chutzpah – and the support of wise advisors, who see you and get you – to leave the well-trodden path for the road less travelled… that takes you to the business and life you’ve always wanted.

Interested in hiring the three of us as your business coaches? We are looking for a new Advisory Council client – email our Relationships Concierge, Jane, at to set up a conversation to talk about what’s going on in your business and where you want to go.

Stella is cofounder and copywriter at Las Peregrinas, a creative and consulting agency. As our resident word nerd, she writes copy and points out the stories everyone is living and telling through their work. She is also fun at parties.

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