The shadow of goal-setting

👋 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,

Hope you had an energizing, connected and joyful July long weekend (or whatever it was you were needing).

I spent mine at our new home in the Catskills, which is proving to be the biggest gift—especially as someone who's been recovering from chronic fatigue.

With the start of July comes the second half of the year! Already?! I know.

Today's newsletter is here to help you set up both consciously and strategically for the back half of the year.

We'll talk about:

• My own personal struggles with goal-setting as a startup founder

• Dr. Lisa Miller's research on "achieving awareness" and "awakened awareness," and why we need both

• 6 steps for your H2 visioning and planning

Plus scroll down for two events in July you're invited to. 💚

The Shadow of Goalsetting

I remember clearly, when I was building my first startup, we'd enter each year with big plans for what we wanted to accomplish—fast growth, big audience and revenue figures.

As the Head of Ops, Finance & Growth, I led our projections process—looking at our data, our growth budget, incorporating estimates from my co-founders—to come up with the figures we'd aim for in a given year.

When I look back with honesty, there was a subconscious part of me that was quite optimistic in these sessions about the numbers we should aim for, but not always from a healthy place. Sometimes it was from a place of attachment, of need. There was a subconscious thread of: Maybe if we hit these numbers, I'll finally feel enough. Maybe we'll get the recognition, we'll be closer to an exit. All milestones I unconsciously believed would make me feel whole one day.

By the end of the first half of the year, I'd sit with our H1 actuals and our projections for the year and think to myself, "oh man, we've got a long way to go." The numbers I set at the beginning of the year didn't feel energizing—they felt suffocating. Another benchmark to measure myself against, and when I failed, to yet again evidence my not enoughness.

This orientation didn't allow me to relate to my company from a place of creativity, wisdom and openness—all qualities that would've supported my ability to lead and grow. Instead it made me feel boxed in—limited in the options, levers and strategies at my disposal. It became about perfecting the known instead of opening to new ideas and possibilities.

I was trapped squarely in what Dr. Lisa Miller calls "achieving awareness."

Achieving Awareness and Awakened Awareness

In her book The Awakened Brain, Dr. Lisa Miller shares an fMRI study she conducted that illuminated that we all have two modes of awareness—achieving awareness and awakened awareness—and that it's up to us which one we engage.

Achieving awareness is the mode many founders—myself included—know intimately. It's the perception that our job is to organize and control our lives and businesses, and its core question is essentially: how do I get and keep what I want? To be clear, this mode isn't bad. It's what lets us focus, commit, execute, and actually hit the milestones we set. You can't build a company without it.

The problem is when it's the only mode we're operating from. Miller's research suggests that overused, achieving awareness literally reshapes the brain, carving pathways of depression, anxiety, stress and craving.

When we live exclusively here, we develop a perceptual problem: an inflated sense that everything is on us, that life is an inert stage and we alone have to make good things happen and prevent bad things from happening. Even when things ARE working, it doesn't feel like enough. We want more and try harder, trapped in a cycle where no amount of success extinguishes the craving.

This was me with our projections. Hitting the number was never going to fill the hole, because the hole wasn't a numbers problem.

Awakened awareness, on the other hand, is the perception that life is happening with us, not just because of us—and it's the mode many of us founders have to consciously cultivate. According to Dr. Miller, with awakened awareness we don't abandon our goals, but we do loosen our grip on them.

Instead of relating to life as something we act upon, we relate to it as something we're in dialogue with, asking "What is life showing me now?" From this place we perceive more options, more connection, more creative leaps. We trust and open to the unfolding of life.

The hard moments and seasons are still there but we can perceive them with a wider understanding of how they fit into the big picture and how they’re serving us, teaching us and shaping us into the leaders we’re growing into.

One mode isn't better than the other. Achieving awareness moves the ball down the field. And awakened awareness helps us decide where the ball should go, see the whole field, and understand why we're even playing in the first place. Our most important decisions can't be made from achieving awareness alone.

Looking back at my startup journey, engaging from awakened awareness more of the time would've made building not only more enjoyable, but more impactful. It would've opened me up to possibilities—creative ideas, innovative partnerships, growth strategies, ways of doing business—that weren't available within the narrow scope defined by my achieving awareness.

I also strongly believe spending a more balanced amount of time in these two awarenesses would have greatly decreased my chances of burning out from my company. Trusting the unfolding of my path would’ve had a meaningfully positive impact on my chronically activated nervous system. Trusting that we’re being held and guided by the universe is the ultimate way of signaling safety to our nervous systems.

How to Set Up For H2 

So with this understanding, I want to leave you with a way of planning for the back half of the year that taps into both states of awareness. A practice that leaves you feeling hopeful, inspired and energized by your goals and your plan to achieve them.

1. Review Your H1 Actuals

Before you look forward, pull up your results from the first half of the year and notice how you're relating to them. Is there any judgment? Shame? A quiet voice saying you should’ve done better?

You don't need to change anything here. But can you greet whatever is present with self-compassion? If an inner critic is present, can you notice and appreciate how it’s trying to protect you? Send love to this part, as well as the one that’s feeling any of the shame, the not enoughness or any other hurt that may be present.

Then take a few centering breaths and consider:

• What do I want to celebrate from H1? What am I proud of?

• What happened in H1 (the good and the bad) that helped shape me into the leader I know I’m meant to become?

• What ideas and possibilities opened in H1 that I didn't plan for?

• Where did I receive support and guidance that I wasn’t expecting?

• What didn’t work out as planned, and what might that be pointing me toward?

2. Reconnect with Mission, Vision & Values

Take a moment to reconnect with your mission, vision and values. You might journal on the following questions:

• Why did I start my company in the first place?

• What is the bigger idea I'm advancing through my work?

• What is the world I'm seeking to create?

3. Visualize

The following visualization will support you in tapping into your vision for the second half of the year from the awakened brain. It asks what life wants to create through you this year.

Find a safe and comfortable space where you can be undisturbed for 10 minutes, and when you're ready, have a listen. 

I recommend listening to the visualization so you can fully drop in, but as an alternative, you can put on some relaxing music and journal on the following questions:

• What does life want to create through me the rest of this year? What does the universe want to express through me and my business?

• When I imagine a second half of the year where I feel expressed in my gifts, wisdom and creativity, what might that look and feel like?

• When I imagine the impact I'm having—on my customers, my team, the world—what might that look and feel like?

• Take yourself to 6 months from now. It's the end of December, you're looking back on the year, and you feel empowered and proud. What’s unfolded?

• When I envision what's unfolded, how does it feel in my body? (Do I feel relaxed, alive, open, light, at ease?) What's the bodily sensation associated with this?

4. Plan

Now that you've tapped into your vision for the back half of the year from your awakened awareness, you can invite your achieving awareness back online to plan out the finer details.

Block 60 minutes for this - your goals are worth an uninterrupted session.

For each goal or objective (and I'd recommend 1-3 major ones):

1. State your goal or objective for the rest of the year This is your opportunity to take what came through in your vision and translate it into a simple and clearly-stated objective that's easy to understand.

2. What does success look like? How will you know if you've achieved it or not? This can be quantitative (e.g. we're serving 10 customers) or binary (e.g. we launched the product or we didn't). Describe this vision in more detail.

3. What will success feel like? E.g. I'll feel proud, empowered, alive, enthusiastic, grounded, etc.

4. What might get in the way? What obstacles or challenges might I face along the way?

5. What support do I need? List the support that might help you overcome these challenges. Maybe it's your team, mentors, investors, community, a coach, a supportive routine, boundaries, etc.

6. What are the bigger buckets of action I can break this goal down into? What am I aiming to complete in Q3 vs. Q4? This allows you to start to see how you'll move toward this goal, and prioritize your time.

7. What are 3 small steps I can take to get started? This can help you start taking aligned action right away, even if the overall goal feels big and overwhelming. (If you want more support on this, check out Big Vision, Little Steps.)

8. What are 3 ways I can tap into the feeling associated with success (even before my goal manifests)? For example, if you think achieving this goal will make you feel empowered, what are some ways you can feel empowered now? (E.g. journaling on what I’m proud I accomplished each day, screenshotting positive feedback and compliments along the way.)

5. Share

Whether you're a solo founder or have a team, share your goals with someone who will follow up with you (a coach, an advisor, investors, a founder friend, etc.). The research on this says that sharing your goals with someone who'll check in on our progress meaningfully increases our chances of achieving it.

If you have a co-founder or team, consider looping them in from step one so they can do the visualization and goal planning with you. If you want to learn more about how to then align your team on your goals, check out How to Align Your Team on Strategy.

6. Reorient to Your Goal Regularly from Both Awarenesses

Keep your goal written down somewhere you can see it, and revisit it each week. But not just by reviewing the stated objective. You'll want a way to relate to the goal from both awakened and achieving awareness.

Awakened awareness:

• Each morning, take a few deep breaths, close your eyes and visualize what came through in your vision. Notice how it feels to embody the version of yourself that has achieved the goal. Who is she? How does it feel in your body?

• Throughout your week, find ways to bring yourself back to this feeling, even if it's just for a moment.

• Ask yourself, "How am I being supported in achieving my goal?". Notice the people, ideas, signs, and various forms of support and guidance that are present.

• Engage in activities you know help you feel in flow or prone to creative downloads, e.g. a walk or run outside.

Achieving awareness:

• Sit down at the beginning of the week and decide what activities you’re doing to advance your goal. Carve out time in your week for actual deep work. Ensure you're not simply reacting to emails and your calendar. Set yourself up for meaningful progress each week.

• Close each week with a 10-minute review. Ask yourself: What progress did I make this week on my goal? What's the one thing that matters most next week? Put it on the calendar before Monday arrives.

• If you’re leading a team, do the above activities with them. Ask what they’re doing each week to progress the goal and check in with them on their progress and any roadblocks or new possibilities identified at the end of the week.

And that’s it! Wishing you all of the great energy for your planning and for the back half of your year. Please let me know how it goes.

By the way, if you're reading this and you're earlier in your own spiritual path but curious to learn more, The Awakened Brain is the perfect entry point. Dr. Miller is a Columbia psychologist who spent decades studying spirituality with brain scans and clinical data, so the book speaks to the skeptic and the seeker in equal measure. It shows how our brains are quite literally wired for connection to something greater. I highly recommend it.

Hot Girls Know Hormones

​Hot Girls Know Hormones is a monthly talk series for women who are ready to stop normalizing and start getting real answers — about their health, their energy, their stress, their relationships, their careers, and everything in between.

I’ll be joining for an open and honest talk on July 31st to discuss all things holistic stress management. I’ll be opening up about my chronic fatigue and burnout journey and sharing the real practices and learnings that have saved me, and can support you too. Tickets are limited - you can get yours here.

Within Walks

Join us for our next Within Walk for female founders next Thursday, July 16th 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 that is entrepreneurship, you can book a free coaching consultation.

• Walk with us: Join for our next Within Walk.

• Let’s be friends: on LinkedIn and Instagram. I share more startup content and what’s going on behind the scenes there.

• Finally, tell me how you liked this newsletter. I read every piece of feedback.

Thanks for being here. I’m so grateful.

With love,
Roslyn 💚