Reckoning With My Why (+14 Prompts To Connect You With Yours) | Episode 92

This is an unedited transcript and may not match exactly with the final audio. Thanks for your understanding!

Hello hello and welcome back to the Purpose & Progress Podcast.

I talk a lot about values-alignment, in both life and business. Descriptors like purpose-driven, mission-driven, heart-centered, etc are popular in the conscious business space.

And even in my own brand messaging strategy framework, I describe your mission as your why.

But I’ve been feeling pretty disconnected from my why for a long time now. Not because my clients aren’t amazing, because they are. And not because I don’t think I do good work, because I get good feedback and repeat clients often. But because something beneath the surface and for sure out in the world has shifted.

So this will be my personal experience around this question of why, but I’ll be sprinkling prompts and exercises throughout so that you can hopefully apply these ideas to your own personal and brand evolution.

For some context, to nearly everyone I’ve spoken to lately on a get-to-know-you call or in a check-in email, I’ve been saying I’m going through an existential crisis. In life, but especially in business. I feel like I’m in this space of big transition, but I don’t actually know what I’m transitioning from or, especially, to.

And while exploration and staying open to new experiences is one of my core values, I’m also a bit over-fixated on the how of things, when I could absolutely relinquish less of the false control. Let’s just say it’s a work in progress.

I did a values audit in the past, including a whole episode about it, number 28. And unsurprisingly, I was just as dramatic then, as I called it an identity crisis at the time. I recommend you listen to the whole episode for examples, but here are some of the prompts that you (and let’s be real, I) could use in a time like this:

1. Where are my values showing up and are these values how I want to be known? Aka if anyone were to describe me using these words, would that feel perfectly aligned, or would something feel like it’s missing?

2. What’s actually feeling good about my business? What’s really not?

3. Do I actually know my values and how I personally describe them…and here’s the kicker—without looking them up every time?

4. How do I want to feel in and through my business? And importantly, what makes me feel that way?

In a much more recent episode, I mentioned a 3-word exercise that’s similar to values work, but might feel more approachable if you’re totally daunted by the idea of nailing down official values. I know lots of us wear many identities, have different facets of our personal brand or service offerings, etc, so claiming values forever and always just feels like too much. First of all, nothing needs to be forever and always, but second of all, naming and defining the values are just a means to an end. The goal really is that intentional, explicitly values-aligned action. If you’re able to lean more on intuition for that decision-making, especially if you’re a solopreneur without a team you need to bring on board with you, then you do you.

Regardless of whether it’s those 3 words to create a vibe check or brand values to guide you, or anything in between, ask yourself how and where you can embody those ideas. If you’re trying them on for size and it’s feeling good, more good will follow. Both in terms of your own actions and energy, but also in attracting perfect-fit people. It breeds confidence in yourself AND with other.

So anyway, I’ve been thinking a LOT about what is my personal why. For me, it’s not separate from my brand why. Maybe for you it is. There’s no right or wrong here.

And I’ve even asked the most basic question: what is my business in service of? Why does it even matter? I had to literally voice memo myself through all this on a walk. (Fellow verbal processors, please let me know I’m not alone here. The base of this podcast episode literally started from the transcript of that heart-to-heart with myself.)

And when I reeeeally think about it, it’s the macro and micro coming together. It’s the personal interactions of making someone feel lighter and more excited and more validated in taking action toward their own dream and calling in their own perfect-fit people. And it’s about being part of this collective economy. I love love love the idea of getting more money in the hands of more women.

And at the same time, getting more big ideas out into the world. Because so often, our ideas just live in our head and they’re not helping anyone in there. They’re not changing the world. And I am a bit of an eternal optimist on that front—I do believe that we can affect change. I do believe that what we think about and what we care about matters. And even more than that, it’s what we do with that deep care and intention and passion and curiosity that actually makes a difference.

So the way we talk about what we care so much about is really important. It’s important because we need more people to buy in figuratively to the world you’re making a reality. And literally buying in, spreading that money around. The money element really does matter. I have a whole playlist of money-related podcast episodes that I’ll link in the shownotes.

But the money matters because it determines our ability to sustain ourselves. I’m not talking about a money grab, a get-rich-quick-then-be-an-awful-human scheme. It’s not about hoarding money. Although sometimes I lean that way on the spectrum. It’s about building wealth so that we can support more people and more causes and more movements that we care about, so that we can see change in the world.

Because, yes, we can change via free interactions. This podcast is free. The way we communicate with the way we talk to someone, and what we make them feel absolutely shifts the energy and the trajectory of their day. and we never know if we will trigger something in someone that’s forever for the better or forever for the worse.

but we do also know that having money gives us time and opportunity and space to explore and to breathe a little and enjoy life and commit to the things that we care about and research the things that need to be researched.

I was just listening to an Amy Porterfield podcast episode, I’ll have it linked—I’ve actually never followed her content even though I know she’s one of the most famous online business and marketing gurus out there. But she asked what would you do if your revenue was double, triple, etc. And this hit home for me because I had already struggled with revenue goals in the past. I’d set them, use them as my computer password because I heard that helps manifest it, track monthly, etc. Then be wildly disappointed when I didn’t make it.

Or even last year, I’m pretty sure I exceeded my modest goal because I finally set a realistic one, not a huge stretch one. And I earned WAY more then I had since becoming a mostly-full-time mom 3+ years ago and going from probably 60 hours per week of worktime to maybe 20 on a good week, most like 10 on a typical one.

But then I realized, I have nothing bookmarked for this money. I’m not saving for anything specific. I’m not eager to grow this part or invest in this or outsource this. I had no vision or aspiration or anything exciting tied to this revenue other than I need to make money to feel good and prove to myself that I’m a success, whatever that means. Actually, a great prompt around that in a minute.

So when Amy asked what would change, I think her example was with $200k in revenue, my first thought was honestly, nothing. My capacity to vision around this is 0. But then I sat with it (on a completely different day, time, and place to be honest) and I realized I’d outsource a TON. Even things that I used to wear as a badge of honor that I’m just more than exhausted doing. Bookkeeping, out of here. Sending proposals or ever touching my CRM in any way, out of here. So I guess that’s a very well-versed VA or an OBM situation. Repurposing content, out of here. (Caveat, I LOVE creating the original long-form content, just not splicing it up, making sure it’s coherent and cohesive, determining when and where to post, etc.) Again, specialized VA or some sort of content manager. Investing in a coach or tight-knit community. Someone or somewhere to hold space for me, like I do for my clients.

And then I even got to thinking how it’d be nice to have a junior copywriter give a first go at clients’ website copy or one-pagers because I actually like making something better more than I like creating it from scratch. That’s one reason I set up my month-by-month messaging momentum offer the way it is—it’s feedback-based, rather than me creating any specific deliverables. I’ll have that linked in the shownotes if you want my eyes and brain on your copy, content, and big ideas.

I also got to thinking how great it would be to have a web designer and graphic designer and social media manager and blog post writer and all the things on call. Basically a fractional agency. Or basically calling people in the way I’ve been brought into projects in the past to do the messaging and/or copy and they go on to do the rest of the creative scope.

This would center me in relationships with my clients, their big ideas, the skills that other people thrive with. And I’d have “control” (using that in air quotes) over the quality and vibe and essence without having to be in the weeds.

Side note: I LOVE watching people thrive in their element, especially in their creative power. This is basically why Bob Ross was so popular, even if people never picked up a paintbrush of their own. There’s nothing I find more relaxing than watching YouTube makeup, styling, home decor, art channels. Just people doing their craft and loving every second of it. So maybe I AM supposed to be an agency owner. I’ll report back.

Ok, and then back to this idea of success. First of all, I edit out success/successful in almost any audit or co-creation session I do with clients because it’s SO arbitrary, SO over-used, and SO generic. Your success and my success and Joe Schmo’s success are likely very very different. So a great prompt for you is: What does success look like to me?

I answered this for myself a while back and came up with Success means taking AND encouraging confident, meaningful action. And I think that still rings pretty true. I want there to be the feel-good, do-good element to everything I put my energy behind. I’d actually love to know what your answer is. Drop me a voice memo or DM or email, however you prefer.

Anyway, back to the main question I’ve been grappling with: Why do I do the work I do? And even one step removed from that, what do I even do, at the core of it all?

I’ve been trying to understand whether I even do brand messaging strategy like I’ve been claiming as a title and theme for years. Or do I really do values alignment? The idea of inspiring and initiating and facilitating values-aligned decision making, getting people on board because of those shared values, really resonates with me.

I would love, love, love to be doing more of that decision-making stuff in team settings, even more operational settings. Actually, at the beginning of being an online business owner, I thought being an OBM sounded really interesting and in line with my past experiences. Now that my ADHD has been way more activated in my brain and lifestyle (thank you, motherhood), I do not think I would make a particularly good OBM. Or I probably still would, but I think I would be drowning in the day-to-day details of it all on the inside. Aka not the vibe I’m going for.

But I do think that I’m able to be that fractional strategist with an eye encompassing the entire brand experience, and the entire question of how do your values manifest? They manifest in your policies, both client-facing and internal. They manifest in your purchasing decisions. They manifest in your work-life balance, whatever that means to you. They manifest in your communications, your marketing, your visuals, your website accessibility. It all matters. It all adds up. I’m good at seeing where they all connect and where there are gaps. And I’d love to be doing more of that with bigger companies. Not because I don’t love my fellow solopreneurs, personal brands, small businesses. But because bigger companies have more reach, more staff, more customers, more money. The potential for impact is not necessarily bigger, but it’s different in a way I’m really curious about.

So while I do values-aligned messaging, I’m really in the business of connection-building, connecting ideas and people and movements and money and power.

I’m one of those people that’s fascinated by what people do. When I was a kid, I went through phases of documenting my day like I was an investigator or journalist, or capturing names and descriptions of people I’d come across furniture shopping with my parents. In college, I thought I’d study phychology because I wanted to understand what made people tick, but it turned out to be way too clinical and I discovered anthropology, which is basically what makes cultures grow and change, so not too far off. And now, obviously I’m distilling what’s in the head and heart of a founder or leader and translating that to the person who needs and wants exactly what they have to offer.

And one of the first things I want to know and talk about when I meet someone new is, what do you do? I feel like a lot of people who aren’t entrepreneurs couldn’t really care less about their day job or their title or especially the day-to-day of what they actually do. But I think there’s so much more beneath the surface of the careers we choose. We commit so much of ourselves and our identity and our brain power and our energy and our time and our life to the work that we do. So I think we should be energized and excited by it. To the extent that we have that privilege. And I do recognize that living your passion, building a business (especially with a safety net of a community or parents or wage-earning spouse or generational wealth or whatever) is absolutely a privilege.

But even in a j-o-b or a side hustle, and for sure as the CEO of your own brand, I think seeing ourselves in the context of something bigger matters. As contributing. As connecting. As being in relationship with.

And to be honest, on bad days, sometimes I’ve been wondering, why do I even have this business? Sometimes it just feels like a really expensive hobby or like a really big distraction from being the Pinterest mom I want to be. But then I don’t think I actually want to be that Pinterest mom. I think I just want my kids to have a fun, creative, stimulating upbringing, and especailly early childhood. And I think I want to always be bringing the most, even though I’m trying to learn where less is more. Because I’m also sort of the type of mom who’s like why would I buy fancy, official toys when the kid is going to choose a cardboard box and old kitchen spoon any day of the week. And actually, doesn’t that let them learn and grow and explore MORE than some prescriptive toy? Plus, I very intentionally choose to be BOTH primary caregiver AND keep running my business. In part because I also want to be showing my kids that the work we do in the world matters. And that my work outside of mothering them and keeping our household together matters to me.

Ooh, another prompt here. This time from James Clear, one of the few men I follow on the internet, but I love like 95% of everything he writes. He wrote: “Who do you secretly envy—and what does that reveal about what you truly value?” I’ll link the specific newsletter edition he wrote this is, but highly recommend you subscribe to his 3-2-1 newsletter in general. It’s much shorter than mine, promise.

But that secret envy is obviously not a good feeling. Don’t stay in that forever. But that second part of using the negativity as an indicator for what you want more of is great. I sometimes use a similar prompt of “When have you been completely mortified?” or “What would you never put up with, either from yourself or others?” Those really visceral, knee-jerk negative responses can shine some light on the sometimes more subtle, undercurrent values that we want to be able to name and define and act on.

And a note on change. Starting and growing and sustaining my business was new and exciting and a challenge and inherently rewarding when I took it from a side hustle to a full-time business over 6 years ago. The novelty (which my ADHD brain needs) has worn off. So like I said earlier in this episode, there’s a LOT I’d be outsourcing or investing in if I had the funds.

And there’s really only been 1 time when my personal life was particularly heavy that I considered throwing in the towel and just getting a job. I even applied to some local corporate roles and looked at a graduate program. I had a peer mentorship talk me off that ledge and I’m so glad I have the flexibility and clients and collaborators I have because I stuck around.

I know entrepreneurs often joke about being unemployable after a certain amount of time on their own. (Or from the get-go, hence starting their own thing.) I really don’t know what else I would be doing. I don’t know what else I would be excited about. I have a question from a family friend that’s been ringing in my head that I’m now pose to you: If you were to start any other business, what would you start? What needs do you see? What problems can you solve? For whom?

And I don’t know. I actually really do like the idea of a personal styling business or like a home design business. Something around stepping into our identity, something around making us feel good in our skin and in our space. I think that’s so important. And as someone who is going through a big lapse in that, a big gap in feeling grounded and centered and rooted in who I am, this feels really urgent and important.

And what’s strange (or actually, I think way more common than we give it credit for) is that I’m good at seeing that for other people. That’s sort of the work I’m doing for my clients now—giving them the words and validation and space to speak and imagine and grow their big ideas.

And I even struggle with calling myself an entrepreneur because sometimes I lack that vision that I’m able to pull out of my clients clear as day. Sometimes I think business owner or consultant (which is what I actually call myself) is more accurate. I definitely struggle with the play-it-small mentality. Maybe you can relate. Even when I can see ideas from all directions to the moon and back for my clients.

I imagine that’s why people often call me a coach, or that working with me feels like therapy. (I literally had a trained therapist client draw that parallel recently.) Sometimes I wonder if I need to lean more into the coaching angle one day or learn more about either human design or therapeutic practices, like somatic or trauma-informed modalities or ADHD experiences. I could see myself being deeply interested in that, mostly because I’ve already gone down those rabbit holes to some extent.

I will say though, I have some big resistance around certifications and prestige-markers. Almost like the potentially fake expertise that comes from formal programs that I often just view as a sheet of paper. I do think it’s worth learning something from people who have credibly studied and researched and have done the deep dives. But I also think that we can deep dive in a roundabout way. I’m a circuitous thinker, a generalist by nature and on purpose. And while society seems to prioritize specialists, I think my generalist world-view and perspective is a value-add. I’m able to bring ideas from a bunch of different places to a bunch of different new places. And there’s value in that, too. To me, it’s good to have varying interests and points of view and lived experiences and people around you.

So while I’m feeling it’s pretty down about what my why is, where I’m going, what my purpose is, when I REALLY take the time to think on it, it’s fairly clear. I want to facilitate and unlock and encourage and inspire. I don’t think I meant to be a doer necessarily. I don’t think I’m particularly talented or skilled at doing all the things. You can probably find a better-informed, more-practiced copywriter, speaker, business strategist. But I am good at mirroring enthusiasm and ideas, opening up potential, seeing and showing what’s possible, and guiding the way to what’s possible with what people already have innately going on for them. We’re all so much better resourced than we realize and tapping into that and leaning into each other and our past selves makes a difference. And putting language to that so it all feels more real and can bring in and actually impact real people.

When I think about my potential, I do think I could motivate a roomful of women to finally start their business or finally lean into their business or double down on the role they actually want in their job or the salary they actually need to sustain themselves and their families or be the philanthropist or the investor they want to be.

I think there is meaning and value in all of the above because so often we get stuck. And we doubt ourselves or we face setbacks or failures, or the market, or whatever it is. And I just I don’t choose to believe that those are actually limiting factors. Yes, they exist, but the potential to thrive and connect and grow and make your vision come to life is absolutely possible, even in spite of the very real obstacles that may exist. The goal is to build over or around or through them.

As long as we don’t internalize those factors as being inherently part of us and our journey. (Easier said than done. I’m a total ruminator, intellectualizer, overthinker.) But as long as we can bring ourselves out of that internalization, alone or with outside perspective, then we can overcome it. We can actually make moves. Whether it’s just that next foot in front of us, or leaps and bounds toward that big vision.

Ok, so that’s just a tiny glimpse into the existential crisis I’ve been grappling with. It’s not all that serious, but also, it’s sort of all-consuming. I’m sure it’ll pass, until it comes back up again.

Feel free to share yours if you’d like.

And as you navigate any big or small pivot, evolution, new endeavor, whatever you want or need, here’s a recap of all of the prompts I mentioned in the episode:

1. Where are my values showing up and are these values how I want to be known? If anyone were to describe me using these words, would that feel perfectly aligned, or would something feel like it’s missing?

2. What’s actually feeling good about my business? What’s really not?

3. Do I actually know my values and how I personally describe them (without looking them up every time)?

4. How do I want to feel in and through my business? And importantly, what makes me feel that way?

5. What are 3 words that represent the current vibe I’m after or that will anchor me into my next phase?

6. What is my business in service of? Why does it even matter?

7. What is enough for me? And what would change if my revenue doubled?

8. What is my business a means to an end to in my personal life?

9. What does success look like to me? (Bonus: What does it look like to my clients?)

10. Why do I do the work I do? And what do I even do at the core of it all?

11. Why do I even have this business?

12. Who do I secretly envy—and what does that reveal about what I truly value?

13. When have I been completely mortified? What would I never put up with, either from myself or others?

14. If I were to start any other business, what would I start? What needs do I see? What problems can I solve? For whom?