What to do if overachievement is low key ruining your life

👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help founders on the spiritual path of entrepreneurship. Learn about working 1:1 here.

Hi there,

It's been a few months since you last heard from me. I've been navigating chronic fatigue for the last six months, which has meant scaling back my work. (And you better bet my inner achiever has absolutely hated that).

One of the things I've genuinely missed most has been writing to you.

Fortunately, as of a couple of weeks ago, I've been getting some answers. Turns out the cause was mold. I'll share more about that journey another time, but there's something else I felt very inspired to write to you about today.

It’s called the Achievement → Expression Shift, and it’s something I’m going through right now.

So today I want to offer you:

• My reflections on my own real, honest relationship with achievement

• Information on the Achiever Archetype, and how us achievers end up this way

• An introduction to what I call the Achievement → Expression Shift

Next week I’ll be sharing the full framework, including 8 steps for making the shift from achievement to expression.

Before we dive in to today’s newsletter, a couple of announcements:

• If you’d prefer to receive this newsletter on Substack — you can now subscribe here.

• We're doing another Within Walk on Thursday October 8th — join us if you're a NYC female founder.

• I’m hosting a retreat in upstate New York October 16th-18th and we have two spots remaining! Learn more and apply here by Thursday, October 1st.

The Achievement to Expression Shift

Let me start with some context.

When I originally transitioned out of my first startup after burning out, I had been feeling creatively suppressed for, well, basically my entire professional life, and a lot of my academic life too.

So I started writing. Sharing my voice and my inner world for the first time. I opened up about my founder burnout, my relationship to alcohol, my perfectionism with my wedding, making friends in my 30’s.

At a certain point, I decided to launch my coaching practice to serve founders, to support them at the intersection of entrepreneurship and inner work. Which felt very aligned.

But a part of me decided I definitely needed to be successful at that. I needed to attract many clients — successful, influential ones! I needed to earn money, recognition and credibility as a “top executive coach”! To show that I WAS, in fact, good enough — especially since my founder burnout still felt like a personal failure (instead of the gift of knocking me more deeply into alignment, which I now clearly understand it to have been).

Professional success, being seen as accomplished, making myself useful to those around me, has been my way of proving my worthiness for a long time. Before that it was academic and athletic success, and before that it was conforming to family expectations of me.

Because deep down, I did not believe in my inherent value. I did not know and feel the innate preciousness of being a soul in a human body. (Full disclosure, this is still a work in progress!).

So it makes sense that a year into my writing, when I launched my coaching business, I shifted gears and made my content a little more professional: advice on fundraising, managing a team, picking a co-founder, customer growth. Still all through the lens of the inner work. Still more in integrity to who I was becoming than it might once have been.

But the underlying intent was to position myself as knowledgeable, experienced, credible, someone you want to hire as your coach.

(This was before I understood my value as a coach isn't my expertise alone, it's my presence, my compassion, my ability to go deep with clients and to lovingly hold them through whatever is unfolding in their business and in themselves. 💚)

So when a year and a half into this reorienting towards success and credibility, I got hit with chronic fatigue, you can imagine how uncomfortable that felt to my inner achiever.

I'm not gonna lie, these last six months have been INTENSE, emotionally, mentally, physically and spiritually. Not being able to grow my business in the way I wanted to felt like a huge, gaping loss. I had to confront who I am if I'm not achieving, building, and proving my worth. The achiever parts of me were frustrated, disappointed and anxious.

And underneath those achiever parts? Were the younger, hurt parts of me that felt the grief of not being enough, not feeling valuable as I am. That pain ran deep and gosh it hurt.

Over the last six months I've spent hours down in the underworld with those hurt parts, sobbing uncontrollably, feeling their pain, being with it all. Not distracting away from it with alcohol or social media or romantic relationships. Not achieving my way out of it (as that was simply not an option in my fatigued state). Just feeling this old, deep pain.

In doing so, I realized that when I can just be with that pain from a place of presence, of compassion and love, it's actually fine. It's okay to feel this pain. And when I could allow that pain to be expressed and felt, it could be released from my body after years and years of living under the surface, quietly running the show.

And that felt cathartic. Freeing.

As I went through that process day in and day out, I started to lighten. Possibilities that I hadn't allowed myself to consider out of fear started to come into the foreground. Versions of who I could be that I've known are there deep down started to become more available.

The inner achiever softened a little bit. Making space for a deeper, more present me to emerge.

Like my burnout, my fatigue was also a gift. It stopped me from just building another business out of a need to prove my worth. It recalibrated me back to my purpose. To my soul's journey. To the way I'm meant to contribute while I'm on this planet.

So what is that??

Well, to be clear, part of my work is at the intersection of entrepreneurship and inner work. Helping founders grow their conscious leadership. Guiding them throughout the spiritual journey of entrepreneurship.

BUT, there is another part of my true purpose that has been shunned to the shadows, a purpose that sounded too obscene to name out loud. That had parts of me asking “Really? You? Who do you think you are??”

And that purpose is to help people wake up on their own consciousness journeys and to align to the work and lives that are truly meant for them. In part, through my own personal storytelling and teachings.

Both aspects of my purpose are important. Both are needed in the world. But I'm seeing more and more clues that I need to lean into the second one a little more than I have been.

In the last week, several people — both potential clients AND friends and family — have come to me knowing they need to make changes in their lives to align more closely to their highest potential.

People are waking up to this more and more.

And we need this! With the current state of the world, we need more people waking up to their deep desires, to their gifts, their true scary-to-say-out-loud purposes, if we're gonna have a chance of righting our world together.

IMHO, we don't save the world by overachieving at wealth, status, power, beauty, longevity or whatever else we think we need to acquire or optimize to be seen as enough. Acquiring those things is not what gives us the meaning and deep connection — to self, others and the world — that we're seeking deep down.

We right this ship together by coming home to ourselves, by healing enough to start actually, deeply caring about others and the world around us, and by allowing our paths to unfold, trusting that our deepest intuition will lead us to our fullest expression and most meaningful impact.

We need to shift away from the path laid out to us by well-intended parents, teachers, bosses and authority figures, by social media, big tech and wrongful leaders, by a harmful, patriarchal, extractive culture.

We need to shift instead, towards the true expression of our souls.

And okay, this path is obviously not a simple overnight thing. It's A LOT for most people and it takes time, patience, trust, and commitment.

It's especially hard in a society that subtly orients that precious time and energy towards things that don't actually make us happy in the end.

And it's especially hard for those of us that are natural achievers, that subconsciously buy into this thinking and chase it hard in order to prove we are valuable, and thus safe.

You know what actually feels way better than achievement?

Expressing your true self in the world. Contributing your gifts to the healing of the world. Being who you came here to be.

So today I’m going to share more information on WHY re-orienting from achievement to soul expression is so hard, and how we can do so anyways.

But first, let's start with the achiever archetype.

THE ACHIEVER ARCHETYPE

Why So Many of Us Founders Are Achievers

The achiever archetype — the drive to prove your worth through what you accomplish — is something I see very often in founders! 

There are many reasons why us founders decide to embark on a journey that is so difficult, long, and with low probability of success.

Some of those reasons might be:

• We've experienced the problem we're solving and believe it should exist in the world

• We're natural builders, creators and innovators

• We want to have a positive impact on the world, our team, and our customers

• We want the agency and flexibility that can be afforded by an entrepreneurial life

• We’re basically unemployable. Having bosses, being told what to do, the politics - it just doesn’t work for us

• It’s one of the fastest, most effective ways to learn about ourselves and grow

• The financial upside is big

But one of the shadow reasons many of us founders (myself included) decided to do the really hard thing that is starting a company, is to prove that we are enough, that we are valuable, that we are worthy of respect and recognition for doing this impossibly hard but worthwhile thing.

So What Is the Achiever Archetype?

This isn't only a founder thing. It runs a lot deeper than that.

A tool that I used to identify myself as an achiever and understand more about this archetype is called the Enneagram.

The Enneagram sorts people into nine types based on what's driving them underneath — the emotional need behind the behavior. Each type has its own strengths, its own blind spots, and its own growth path.

I'm learning about the Enneagram as part of my coaching training. So I took the test and matched most highly with what's called the “Three Fixation”. (I recommend taking this quiz if you’re curious about yourself and your own motivations.)

This is what my results told me about people who identify as Threes (aka achievers):

“Threes are defined by their desire to achieve. They want to advance in the world and will sacrifice almost anything for success; vigorously pursuing tasks and becoming utterly absorbed in the pursuit of attainment. But they will only choose a task in the first place if it promises rewards and brings prestige. Threes like to stand out. They have a burning need to be admired and see life as a game where winning is emphasized.”

In honesty, this resonated with me, at least Parts of me.

The Connection Between Achievement and Value

The core reason that many of us Threes are motivated by this strong desire to achieve, is because we do not believe that we are inherently valuable. Instead we think that we must do, accomplish, and provide value to others in order to prove our worthiness.

What does it feel like to deeply embody your inherent value?

My coaching program, Aletheia Advanced Coaching Program, says that:

“You feel an implicit valuing of being yourself, exactly as you are. You feel precious exactly as you are. Even more profoundly, you feel as if you are actually made of the most precious substance – that you are innately valuable through and through.” - Steve March, creator of Aletheia

On the other hand, what does it feel like when you access to your inherent value is blocked?

“You feel deficient. You feel as if something fundamental is missing in you, something very precious. You might feel irrelevant, useless, and worthless. You might suffer with low self-esteem and a lack of confidence.” - Steve March, creator of Aletheia

How Did We Get Like This?

Simply put, at some point we didn't get to experience being valued just for existing, at least not in the way we needed.

For example:

Maybe you received more love when you performed. More praise after a straight A report card, a recital, a win. Psychologists call this “conditional regard,” and children who get it often push hard from pressure rather than enjoyment.

Maybe you got criticism or withdrawal when you didn't. A disappointed face or silence after a loss or a lower grade. You learned to avoid that at all costs.

Maybe you got praised for being “gifted” or “so talented”. You learned to stick to what you knew you'd be great at instead of exploring new things and being okay with being average or making mistakes.

Maybe you were told you were special, but didn't feel seen. Research shows being told you're better than other kids doesn't build real self-worth. Whereas being genuinely enjoyed by your parents does.

And some of it is less obvious:

Maybe you were the easy child. A parent was struggling, a sibling needed more help, or there was money stress or a divorce, so being impressive and low maintenance was how you helped and how you got seen and appreciated.

Maybe your feelings didn't get much airtime. Your difficult emotions weren't attuned to or welcomed. So you learned your accomplishments were what got you positive attention.

Maybe your parents were blocked in this themselves. Parents whose own worth is tied to how their kids turn out tend to get more controlling, often without realizing it.

Maybe it wasn't just home. Schools, sports, college admissions, social media and hustle culture all send the message that your value is conditional. Perfectionism in young people has been rising for decades.

None of this means your parents didn't love you. Most of ours did very much. But love that's experienced as conditional, even when it isn't meant that way, can leave a child believing they have to prove their value and earn love.

How Does it Show Up?

When we don't believe we're inherently valuable, we start to look for all the ways we can prove our value.

For me, this has looked like:

• Setting my sights only on “worthy” milestones that would make others perceive me as impressive, special, and “enough”: from getting into the best schools, to earning a professional designation, to starting a company, to becoming a “sought after” founder coach

• Overextending myself — often pushing through my body's signals to slow down — in pursuit of said worthy milestones, and especially to prove my usefulness to others: classmates, bosses, co-founders, teammates, clients, readers, even partners and friends

• Managing my “image” — in daily interactions at work, on social media and in social settings — to ensure I'm seen for my “positive qualities” (smart, capable, successful, kind, deep, thoughtful, beautiful and all effortlessly so) and not seen for what's in my shadow (too much, not enough, cringe, lazy, pathetic, self-absorbed, awkward, incapable, trying too hard)

• Criticizing myself as a form of motivation to be better. Replaying what I've said, done and how I've presented myself in past interactions, scanning for all the ways I could've shown up “better” to prove my worth, and shaming myself when I “messed up”.

These are just a few of many many examples of my own achieving parts, and there are so many more ways this can manifest. So I'd love to turn it over to you for your own reflection.

Reflection Prompts

• In what ways did you receive or not receive the valuing you needed in your childhood from your parents/caretakers?

• How did this lead to a belief that being valued was conditional? Conditional on what?

• What did you learn to do to prove your value? How has this manifested throughout your life?

So, this is a lot to sit with and reflect on for now.

If this resonated with you, and you’re feeling ready to to make the shift from Achievement → Expression, watch your inbox.

Next week, I’m going to be back with the framework to actually shift from orienting to life through a lens of Achievement to the lens of Expressing your Soul.

Thanks so much for reading and being here — I’m so grateful for you.

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October 16-18th in the Hudson Valley. Eight female founders and leaders.

This retreat is an invitation to examine and release the patterns that are holding you back from the most full and expressed version of yourself.

You can expect facilitated sessions with an intimate group, movement and somatic practices, embodied rituals, time in nature and nourishing meals.

Learn more and apply here.

Within Walks

Join us for our next Within Walk for female founders next Thursday, October 8th at 7:30am.

Within Walks were created to make space for meaningful conversations with other founders who are bravely walking the path of entrepreneurship.

​Each walk, we grab coffees, do a round of intros, introduce our conversation theme for the day, and walk together along the Hudson river.

​You'll leave feeling more open, expanded and in community with others female founders.

Join us!

• 1:1 Coaching: If you’re curious about how coaching can support you on the spiritual path of entrepreneurship, you can book a free coaching consultation.

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Thanks for being here. I’m so grateful.

With love,
Roslyn 💚