A few things I love from my desk: a pen that feels heavy and luxurious that I’ve owned many years (it’s refillable, I love having little things like this that stay with me a long time), my fave pencils, iconic stationary (love the pink too. I need a wax seal), a fancy alternative to post-its that I love writing notes on, an Astier vase as a little pen holder, le pens, and a tiny yellow notebook (comes in a million colors). All of these and more stationary here.

For me, these items feel just right, which is my goal for my professional life overall… to figure out how to feel like I’m in the right place doing the things I’m here to do, offering up something from the heart. Recently, I had a call with a founder that gave me that feeling. She scheduled the session to discuss her sustainability strategy, but as she began telling me about herself, what she’s putting out into the world, and her values and motivations, we entered into a deep discussion about the positioning of her brand and communications strategy. At the end of that one hour conversation, she had refined her company’s mission and values and had a clear set of actions to take to purposefully nurture existing customers, attract new ones, grow her social following, and increase revenue.

When the call ended, I was lit up. Wow. We accomplished A LOT in an hour. That was work that did not feel like work. I started thinking about how I could have more conversations like that. Since it was a one hour strategy and branding call, why not simply invite more women to book a session? I then wondered if I am qualified to offer such a thing and reminded myself I have launched and operated successful companies, referred many millions in revenue to them from personal and business Instagram accounts, and grew a social following of 100K+ without any paid advertising. I’ve also given this kind of advice to plenty of founders over the years organically - and for free.

Spur of the moment, I wrote up a description of the strategy call, posted it online, shared it in my story, and bang people signed up.

I have wanted to work with women entrepreneurs for a long time. Not just be around women, but have personal conversations and really connect. And not just connect, but do so with purpose that leads to an impactful outcome. And now that I’ve had a few conversations focused specifically on brand identity and how to utilize Instagram as a tool to establish and scale that identity, I can see that this is something I can do that delivers the connection and impact that lights me up.

I love these calls. It feels adjacent to writing you this letter. In its simplest form, it’s about women connecting and sharing stories and ideas.

But in regard to finding a fulfilling career... On the one hand, it’s so cool that many of us have the privilege to custom tailor from scratch a way to make money and offer value that is well suited to things as specific as how social we want a typical day to be or how much variety we’d like to experience (the self employed economy we now live in affords us the chance to do more than one thing).

On the other hand, it’s a lot to ask of us to make an array of complex decisions with infinite choice across every facet of our careers. Gone are the days of top down career selection - relying on things like college majors or job listings to determine what we do for work.

We now have the opportunity to approach things from the bottom up, crafting a totally unique professional life. To do this well, we have to gain clarity about who we are, what we’re good at, what we enjoy, what fulfills us, and so on, so we can figure out how to make what we do align with who we are at our core and lucrative enough to pay our bills (and ideally fill our investment accounts).

We can be remote, in person, or hybrid. We can be freelance, fractional, a consultant, or employed full time by a business we don’t own. There are a ridiculous number of industries and roles within each of those industries. Ones that didn’t exist even ten years ago. It’s amazing to have so much choice and freedom, but it’s also overwhelming to thoughtfully make decisions amidst endless possibilities.

We certainly don’t stumble upon effective tools to figure all of this out. The school system doesn’t do much to assist beyond presenting a list of subjects and majors (which, depending on how you see it, may actually stifle our progress by limiting us to a narrow menu of possibility).

Enter: one small step we can all take to get centered and gain a little more clarity. It’s a list of questions that will prompt you to take stock of who you are and what sort of professional set up (and even life) is right for you. They are inspired and evolved from The Artists Way and various other books and courses I’ve encountered over the last decade, including a group my dear friend hosts about once a year in Ojai (happy to connect you if you’re in the area).

Whether you’re actively looking to switch up your career, feel settled and content professionally, or are somewhere in between, I think it is very, very helpful to check in with yourself on this about once a year.

I find that every time I sit down to answer these kinds of questions, I’ve evolved and am looking for something a little different.

We all have a tendency to pigeon hole ourselves over time. We are constantly developing ideas about who we are. It’s a collaborative process between us and our environments. Responding to these prompts is a way to check in, recalibrate, and perhaps break out of the various boxes we might have put ourselves in. 

If you know anyone navigating a big decision or transition who could use some support, feel free to forward them this email. 

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