Are you in the first few years of self-employment? Or thinking about one day embarking on that path? If so, today’s note is for you.

For me, the early years were full of places I thought would feel like paradise, and instead felt like the wilderness. I can remember vividly one moment, several months in, sitting in our bedroom telling my husband through tears, “I can’t believe how hard it is. I just didn’t expect this.” 

I was lonelier than I thought I would be. A lot of days it felt like I was wandering around – both literally, as the hours passed slowly, and metaphorically, as I explored one or another direction of how to use my time – all of them feeling aimless. And there wasn’t a big positive response to my work, I felt so discouraged.

Talking with hundreds of women about this over the years, I’ve learned: the early days are tough for most of us. Sometimes the challenges are external – no one is buying my thing. Sometimes they are internal – I’m isolated. I’m confused. I’m scared of putting myself out there even though I know I need to.

Today I want to share a few of the things I struggled with during that season, and what I learned that helped.

1. The doing does feel different than the dreaming, and that’s okay. I took my leap onto an entrepreneurial path with passion and inspiration. But after the honeymoon phase ended, the actual work felt very different than the dreaming had. I think these early difficult feelings are absolutely normal and most important: it doesn’t mean the path you’ve chosen is the wrong one for you. 

However, my experience wouldn’t have been so painful if I had just understood one important thing…

2. The first phase of a new venture is *not* about running a thriving business. It is about the process of figuring out what product or service is going to work out there in the world. The early years are about a kind of structured trial and error to find out what your business is going to be. 

We start our entrepreneurial journeys with lots of unanswered questions. Who will want what I have to offer? What of all that I have to offer is there truly an audience for, and what do people actually want to pay for? What language do I need to use when I talk about it, so that my audience grasps what I’m talking about and sees it as for them? What can I build a sustainable business around?

The first many months, or often the first couple years of the entrepreneurial path, are about answering these questions by trying things out in the world. They are about putting things out there to an audience and learning from what happens. If you see each trial that doesn’t work as a failure, your morale will be absolutely doomed. If you see them as exactly the process you are supposed to be engaging in, and you engage in it deliberately, you’ll be able to see all the learning as progress. And if you know that’s what the beginning is about, you can set your expectations – both financial and personal – accordingly. 

3. Go forth and be with the people.  If you’re an extrovert like me, you especially need to design ways to MAKE HUMAN CONTACT in the early days. But even if you are an introvert, you need your healthy dose of this, too. There are two types of human connection I’d like you to think about here.

The first is your water cooler. Where are you going to get your water cooler conversation now that you aren’t showing up to an office? I’ve used co-working spaces, informal co-working groups (rotating in members’ homes), online courses (and hosting in-person gatherings of those course participants from my area) to meet this need for myself.

Second, go do your work with your people. Most of us know we’ll be working with lots of people when our businesses are humming along. But in the early days, when we likely don’t have a team or many customers, we can get very isolated, very quickly. The more we are being perfectionistic, overthinking things, and using classic brilliant women hiding strategies, the more this is the case.

So do your work with your people in whatever scrappy and immediate way is available to you. Send a quick email to get a first few clients through word of mouth. Whatever group you are planning on facilitating someday, start the pilot version NOW. Commit to having five conversations with potential customers each week. Get out there with the people. It will feed your soul, fuel your productivity, and keep you tethered to the real world.

Got it? Good! Please share with another woman early on her entrepreneurial journey if you feel this could help her, too.

Sending love to you today,




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