Big Vision, Little Steps

Hi there,

I hope you had a nice long weekend! I escaped the cold in NYC by flying to Miami for a friend’s bachelorette. It was a nice preview of the Florida weather I hope we’ll get for my own wedding in Sarasota in two short weeks!

Speaking of, I’m going to be taking some time off around my wedding so you won’t get a newsletter on March 4th. I’ll be back in your inbox on March 18th, hopefully with a wedding pic to share.

Today I’m excited to get into the topic of how we can make progress towards our big goals and visions, instead of feeling overwhelmed, procrastinating or letting our fears and perfectionism keep us frozen in place. Can you relate?

We’ll cover:

• How our big goals can keep us stuck in place

• 7 strategies — both tactical & magical — for releasing ourselves from the stuckness and continuing to make progress

• 5 female founder newsletters I’m reading these days

🌊 Where we go deep on how to build with integrity and live a meaningful life.

 If you’re reading this newsletter, I’m guessing you’re someone that has a big vision for your work and life. You likely have quite ambitious goals and high expectations for yourself.

In many ways, that’s amazing. I truly encourage it. We can’t live our dream lives and achieve our big goals if we don’t allow ourselves to envision them and set them in the first place. 

And, at the same time, our big dreams and goals, our high expectations, can at times leave us feeling frozen and stuck, unable to take the actions we know we need to take to move towards them.

Have you ever procrastinated starting to work on a project, a task or even a business because it felt overwhelming and you didn’t know where to start?

Have you ever felt like it would be safer not to act, because to act would be to risk failure, or even just fall short of your goal?

I can relate. I have big visions for Within, of what it can become, how many people I can serve, of the financial abundance I can experience. It feels incredibly aligned. And I believe in my ability to get there, truly. And so I’ve set big goals for myself, around what I can accomplish.

Some days I feel motivated by these goals. And other days, I feel overwhelmed. I doubt myself and my abilities to hit my goals. I think about all the ways in which I don’t feel ready yet, to embody that version of myself I most want to become.

And I allow that fear to dictate my actions (or lack thereof). In many ways it blocks the energy I need to be in to attract the right people and opportunities to my business. It blocks my creativity. It stops me from being in flow, and fully in an attitude of service.

So today I want to share with you the seven strategies that I’m practicing, and that you can use too, to release the stuckness and move towards our goals with confidence, devotion and ease.

7 Strategies for Achieving Your Goals

DIRECTION IS MORE IMPORTANT THAN SPEED

The first thing you’ll want to do, is to make sure the actions you’re taking are moving you in the right direction in the first place. Get clear on why your goal is your goal.

Is your annual goal moving you towards your ideal life five years from now? When goals are aligned to a deeper, aligned ‘why’, all of the actions to get there will flow more easily, than if you’re working towards a goal that is not actually aligned to your authentic self’s desires and values.

For example, let’s say your goal is to fundraise for your startup this year. Is running a venture-backed startup truly aligned with the best version of your life? Maybe it is, because you are so aligned to the company’s mission and the best way to bring it into the world and scale the impact you want to have is by raising outside funds. You feel energized by the pressure and faster pace that comes with this and are determined to find supportive, aligned investors.

On the other hand, maybe you’re attached to the validation you’ll feel, for your company and yourself, if you do fundraise. You dream of the Forbes headline and the possibility that you will finally be “enough”. And then once you’ve successfully raised, you realize that the hypergrowth model required of you doesn’t fit with the most authentic, aligned way for you to build your company.

Check in with the why behind your goal to ensure it’s aligned to your true purpose and values before putting in all of the effort to go after it.

You can be working hard, moving fast, crushing your to-do list, but if it’s the wrong to-do list, moving you in the wrong direction, it doesn’t matter. 

There's an aviation concept called the 1-in-60 Rule. It says that a 1 degree error in heading will cause a plane to miss its target by 1 mile for every 60 miles flown.

This concept can apply to your work and life too. Tiny deviations from your optimal course are amplified by time. Moving in the wrong direction now can create a big misalignment later. So again, it’s best to get clear in the present on what your optimal course really is.

TAKE  “TURTLE STEPS”

This is a concept I learned from Martha Beck in my Wayfinders coaching program. According to her: “Turtle steps are very small, easily achievable steps to which we have almost no resistance. They can be so simple and so small as to seem ridiculous or inconsequential, but they’re not. 

If tasks feel doable, we’re much more likely to move into action. Evidence suggests that we persist in things we take in smaller steps. This means the smaller the steps we take, the more likely we are to achieve our goals. Though they may run counterintuitive to cultural values of “higher, faster, stronger”, Turtle steps enable us little-by-little to make successful progress on those seemingly insurmountable tasks or improbable dreams.” 

Bring to mind a task or project that’s feeling overwhelming. Now ask yourself, “What is the largest possible task that I can easily do without resistance?”. Check in with your body. When you think about doing this task, do you feel any tightness, anxiety, or uneasiness take over your body? If yes, then it’s still too big. Break it down into something even smaller. Maybe it’s engaging in something for 15 minutes. Maybe it’s just doing some research about what you need to do.

For example, maybe your task as a founder is that you need to raise a $1m seed round. Feels like a pretty big, scary, overwhelming project. So let’s break it down into a few sub-projects:

• Determine the investment vehicle and fundraising timeline

• Create a pitch deck and prepare for investor meetings

• Schedule investor meetings with aligned investors

• Conduct investor meetings

Okay great so you have four major sub-projects around fundraising. But… each one is still feeling pretty overwhelming. So let’s pick one and break it down further. We’ll take “schedule investor meetings” and break it down as follows:

• Make a spreadsheet of stage & category appropriate investors

• Find people that can make a warm intro to these investors 

• Write a forwardable email that mutual connections can send to investors

• Once connected, schedule time with investors

Okay so perhaps now it’s starting to feel more manageable. But… you check in with your body and “find people that can make warm intros to investors” still feels too overwhelming to move forward. Let’s break it down once more.

• Make a list of the individuals at the investor firms I’m interested in

• Use LinkedIn to see who in my existing network is connected to that person and ask those people for a warm intro

• Reach out to my friends who are founders to see if they’re willing to make warm intros to their own investors that are a good fit

• Network via founder-investor focused events, founder communities, and pitch events

And so on and so forth. I’m going to stop here for the purpose of my word count but you could take any of these tasks and continue to break them down if any of them was still giving you resistance. 

VISUALIZE YOUR PLAN

One way to visualize your Turtle steps for a big task is using a mind map, as shown below. This is a great way to take all of the ideas and tasks that are swirling around in your head and organize and visualize them on paper, which will naturally make it feel less overwhelming. 

You can use a physical pen and paper or you can try using MindMeister which is a free mind mapping tool. 

This is what a mind map might look like for the fundraising example we discussed above. 

OPTIMIZE WHAT YOU CAN CONTROL

When you’re working towards a big ambitious goal, you will naturally encounter setbacks along the way. Instead of allowing these setbacks to feed a narrative of why this won’t work for you, root into your ‘why’ and then focus on the things you can control. 

For instance, you’ve gotten five consecutive no’s from investors. Instead of allowing these no’s mean that you’ll never be able to fundraise successfully, that you’re not a good enough founder, or that investors are arrogant jerks, focus on what you can control:

• Ask for feedback and the reason for the no’s (or reflect on the questions they were asking and areas of the business they were really digging into). Use that information to iterate on your pitch and your Q&A. Practice it. 

• Get more investor meetings on the calendar. The only way to get a yes is to have more calls, practice, learn from them, improve, and keep going.

• Continue working on your investor pipeline. Do more research, find more investors, and request more warm intros.

• Record investor calls and watch them back, observe and make suggestions to yourself for improvement.

• Get feedback on your deck, your pitch, your financial model, and your Q&A answers from any friends that are founders or investors.

• Read books about fundraising, investing, and startups to sharpen your knowledge and put yourself in the shoes of investors.

• Talk to other founders who have successfully fundraised and get their advice and encouragement.

The list can go on and on of the things that are within your power to influence. Focus on those things.

CELEBRATE PROGRESS INSTEAD OF CRITICIZING FALLING SHORT

Ever set yourself an ambitious goal and you fall just short, and so you see it as a failure? Instead of recognizing and appreciating all that you have achieved? You see it as black and white, you hit the goal or you didn’t, when really what you’ve done to approach your goal is nothing short of extraordinary.

For example, you’re raising a $1m round, and you’ve raised $500k so far. And you see this as a huge failure. “Ugh, we’re only 50% of the way there.”. And on the other hand, you’ve raised HALF A MILLION DOLLARS. Like how incredible is that, that you’ve found people that believe in your idea so much, and your ability as a founder to execute on that idea, that they are willing to put a collective $500k on the line. That is a HUGE accomplishment. And seeing it as such, actually allows you to build your confidence, self-trust, and belief that you will raise the full $1m. 

Viewing it as a failure, puts you in the energy of imposter syndrome, doubt and “not good enough”. Celebrating the progress energetically allows you to embody the version of yourself that will go raise that other half. Which story you believe in is up to you!

EMBRACE FAILURE

Failure is a key ingredient to success. 

It’s a tough one for us perfectionists to swallow. But safety is the enemy of success. Be proud of your mistakes. Take a risk, fail spectacularly. And then go out there and fail some more. If you want to be successful, you need to stay in the game. Even when things aren’t working, even when you’re getting no’s, even when you’re making mistake after mistake. Learn from them, know that each rejection is bringing you one step closer to your eventual success and keep going.

If you’re fundraising (or selling, recruiting, anything), embrace the no’s. See it as your goal to go get more no’s, because the more no’s you get, the closer you are to a yes (assuming that you’re learning every time). 

REGULATE YOUR NERVOUS SYSTEM

When you’re doing something that scares you, that you’ve never done before, (which is often the case when we’re pursuing big dreams), this can feel very unsafe for our nervous systems. That’s why sometimes, when we’re doing these new and scary tasks, we feel stuck and unable to move forward (that’s the nervous system’s freeze response), or like we want to avoid and run away (that’s our nervous system’s flight response).

I can remember the innumerable times I experienced a freeze response on an investor call, trying to answer a question but stumbling over my words, unable to articulate the answer that I knew I had somewhere in my brain while my heart raced, my palms sweat, and I was overcome with brain fog.

Here’s what I would suggest if you’re experiencing your nervous system go into fight, flight, fawn, or freeze when you attempt to do any the tasks bringing you closer to your goals:

1. Maintain good nervous system hygiene, especially throughout this period of high growth/stressful events. Get a good sleep, exercise regularly, lower caffeine and alcohol, and incorporate some regular nervous system practices into your day — whether that be breathwork, a body scan, a physiological sigh, or whatever works for you. 

2. On days that are particularly stressful or have big high stake moments, incorporate both rest and ways to complete your stress cycle into your day. If you’re feeling super pent up because you have an investor call that day, can you do a workout, watch some comedy to get you laughing, or seek a hug or some cuddles from a loved one or pet? Can you allow yourself to go lie down and read a book before or after a stressful moment in your day? Or take a walk outside? 

3. You can actually train your nervous system to get less activated by a stressful event before the actual event itself.

You can do this by practicing gently moving your nervous system into an activated state, tuning into the sensations, giving it some space, and bringing it back to rest and digest. 

First, set yourself up in a safe and comfortable space where you won’t be interrupted. Identify things around you that make you feel good (a warm blanket, a candle, a calming song, a plant you can see nearby, the sky out the window, a warm cup of tea, etc.). 

Then bring up the stressful event in your mind — for example an investor meeting, a big presentation, a hard conversation — that you have that day. Just notice the sensations in your body as your nervous system activates (breathing depth & rate, heartbeat speed, tightness in muscles, numbness, etc.). Stay in this place gently observing, until the sensations start to lessen and you get bored. Then return your attention to the things around you that are comforting, slowly allowing your nervous system to come back to rest & digest.

Practicing moving back and forth between these states will allow your nervous system to be less reactive to the stressful situation, so when you experience the real thing, the activation will be less intense.

If you want to go deeper, I  wrote more about the nervous system here.

EMBODY THE VERSION OF YOU THAT’S REACHED THE GOAL

How would you feel and act if you already had what you’re calling in? Now embody that version of yourself and act in alignment with them. 

In the fundraising example, if you’d already raised the $1m, you’d probably feel calmer, more magnetic and more confident in your company and yourself. You’d be in the energy of “I don’t need you, but I do want you as an investor”. You’d feel like you’re doing THEM a favor by allowing them to invest in your company, not the other way around. Can you imagine how different that energy would be in an investor meeting? How you’d show up? What your posture would be like? What your voice would sound like? How confident you’d be in delivering your pitch? How you’d navigate Q&A with ease?

When I was coaching one of my clients on fundraising, we did visualization work around how the meetings would go, how she’d feel, what the interactions would be like if she was embodying that version of herself that was confident and knew it was all going to work out. This allowed her to walk into her investor meetings with that feeling, and ultimately she successfully raised her round!

Tune into the feeling of that future you, and bring that energy into the world.

🪞 Your turn to reflect. Take these prompts to your morning journal or talk it over with a friend or coach.

• Why do I want to achieve the goal I’m aiming for? Does this reason feel aligned for me?

• When I envision a big goal or project, what is the largest possible task that I can easily do without resistance?

• What’s within my control? 

• For a goal that I’ve “missed”, what can I still celebrate?

• What was a time where my initial failures were a key part of my ultimate success?

• What’s one thing I can do to take care of my nervous system ahead of a stressful event?

• How would I feel if I already had what I wanted? How would I show up?

Okay I’ve been obsessed with the trend I’ve been noticing of female founders starting newsletters to talk about what it’s like building businesses, and sharing other aspects of their lives. 

Here are a few I’m currently receiving.

• Mayssa Chehata, founder of BEHAVE, writes about spiritual lessons from entrepreneurship, healing and life. Learn from Mayssa here.

• Lindsey Carter, the founder of SET Active writes about building SET, DTC fashion, life updates & lessons from entrepreneurship. Sign up here.

• Connie Lo, the founder of Three Ships, writes about purpose-led startup leadership and intentional life design. Check out her substack.

• Yael Shemer, the founder of TULU, writes about self-discovery, creative expression and finding balance as a passionate environmental and tech entrepreneur in NYC. Read here.

• Melanie Masarin, the founder of Ghia -- honestly her substack is less about building her company and more just about the cool outfits, products and travels she recommends, which I’m into. And it’s inspiring to see founders with hobbies and identities outside or purely their companies. Get inspired here.

Who am I missing from this list?! Reply and let me know.

• 1:1 Coaching: I have a few spots left for 1:1 coaching. If you’d like support with your goals, book a free strategic coaching consultation.

• Let’s be friends: If you want to see the BTS of building Within and receive more tips and ideas on building with integrity, connect with me on LinkedIn and Instagram.

Alright, thanks for reading today and see you back here in a month!

With love,
Roslyn 💚