10 Lessons From My 1st Year of Business

👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help founders fall in love with building their companies again. Learn about working 1:1 here.

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Hi there,

I was looking at my Instagram account yesterday and realized I officially announced the launch of Within a year and a week ago! 

Time sure flies. It’s funny because my business has come a long way AND at the same time it still feels incredibly new. 🌱

So today I felt called to pause our team building programming to share with you my 10 lessons from one year of building as a second-time founder.

Let’s dive in. 

Where we go deep on the outer work or the inner work of building a startup.

10 Lessons from 1 Year of Within

A year ago, when I launched Within, I went into building my second business with the intention that it would be very different from how I built my first. 

I was coming off burning out VERY badly from my first startup and so I was feeling extremely motivated to not repeat the same mistakes. I had spent several months taking time to heal from burnout, engage in deep inner work and rediscover my identity outside of my first startup. 

As I explored, I felt a deep call to apply the personal development work I was doing personally to a startup context. I launched Within to help founders do the inner work that unlocks aligned, sustainable outer success in their businesses. 

I vowed to integrate my learnings from my first round of building a startup in how I would build my second one. With more awareness of how my unhealed wounds and patterns drive me. With the intention to be driven by purpose, inspiration and curiosity instead of through a need to validate myself through accomplishment. 

I wanted to model this way of building to the founders I work with, to let them know that this is possible for them too. 

What I discovered is that even with those learnings and wonderful intentions in place… it’s still been hard in many ways! 

But in being hard it’s also been an incredible avenue for spiritual growth, for even more healing (woohoo!) and deepening self-awareness. 

And without those, I simply wouldn’t be the coach and founder I am today.

So with all that, here are my 10 lessons I’ve learned from a year of building a purpose-led business.

1. EVEN WHEN IT’S ALIGNED IT CAN STILL BE HARD

Choosing to start your business in an area you feel a deep sense of purpose, passion or fulfillment doesn’t mean it won’t be hard along the way. At the end of the day we’re still human beings at the helm of our companies. We will always, at times, fall into old unhealthy patterns, get triggered, get scared, feel deficient in one way or another, be inexperienced or unskilled. And that will show up in how we build our businesses. 

While my first year of building my business has been beautiful, fun and satisfying, it has also been humbling. It has challenged me. It has asked me to look deeply within myself. To forgive, to be brave, to be curious, to grow, to face myself even when I don’t like what I see. And as demanding as that can be, I wouldn’t have it any other way.

2. ALIGNMENT ISN’T JUST ABOUT THE WHAT IT’S ALSO ABOUT THE HOW

I’ve learned that if I want to build a business that feels aligned to who I am, the life that I want to create and the impact I want to have, it’s not just about the area of my business being aligned. It’s about HOW I go about building.

If I want to attract the people I can serve best and work on the activities that truly give me energy, I need to maintain my integrity in my business everyday: in my coaching practice, in how I show up online and at IRL events, in how I structure my time. In how I develop, market, and sell offerings. In how I take care of myself and my energy. In how much of myself I allow to be seen. I know it alllll adds up to the business I’m building.

3. CREATE YOUR OWN PLAYBOOK FROM WITHIN

The part of me that doesn’t fully believe in my own wisdom, that doesn’t fully trust myself and the universe yet, likes to look at what others are doing. That part says “if I do that, surely I'll be successful too”. I used to do that more in my last business, seeking advice from the founders that were three steps ahead of us, that seemed to have all the answers. 

My logical brain likes to think “x + y = z”. For example: good messaging + more outreach = more calls → more sales. 

What I’ve learned is there is no formula or playbook you can copy that results in the business that’s right for YOU. (don’t get me wrong, you can build a successful business that way, but not one perfectly molded to the person you are and the life you want to live). That needs to come from within. Expose yourself to new creative ways of doing things that expand your mind. Get inspired by people whose values you align to. And then create space for stillness, for intuition to come through. Listen to what feels FUN even though your logical mind says “that makes no sense” or “how will we make money from it?”. Trust, experiment, learn, iterate, repeat. 

4. CONTROL IS AN ILLUSION. AND IT COMES FROM FEAR.

There’s a part of me that’s scared I won’t be “successful” (who gets to decide that definition anyways?). That I will never be “enough”. That I won’t belong, be accepted and loved for the full  me, unless I’ve “made it” (again…definition??). 

That part of me likes to control the heck out of stuff. It makes to-do lists and goes over them in my mind while I'm trying to sleep. It strategizes. It plans what I will say ahead of time. It wants me to read more business books instead of listening to intuition. It holds me back from putting myself in situations where I risk getting judged. It procrastinates and avoids situations that could make me feel some pretty uncomfortable emotions.

It’s doing these things to try to protect me from experiencing pain, rejection, judgment, loss, failure, not being enough. Because I experienced those feelings at one point or another in my life and that HURT. And this part of me wants to avoid that at all costs, not realizing that I’m older now and I have the capacity to be with those feelings. 

What I’ve learned is that the best way out is through. If I want that controlling part to be able to relax — because let’s be honest those things are not helping me, they’re hurting me and they’re keeping me from my deeper wisdom — then I need to show my parts that it’s OKAY to feel unloved, rejected, shame, criticized, not enough, etc. That I can FEEL these feelings and SURVIVE and even THRIVE on the other end. That I can comfort myself.

When that part of me sees that I can be with these feelings, they start to loosen their grip on control. And as a result, my business can be guided by my deeper wisdom, instead of by fear and avoidance of pain.

5. EXPERIMENT WITHOUT KNOWING THE BUSINESS OUTCOME YET

Allow yourself to play, to follow what feels fun. Even if you don’t know how you’re going to monetize it yet. Block some time out for creativity and see where it leads you. Often these are the things that end up contributing to the energetic signature of your business, that resonate most deeply with people. Often they do eventually, directly or indirectly lead to positive outcomes for your business. But when you try to know right away exactly how it’s going to make you money it can tamp down on the creativity, the life, the joy of it. 

For example, in the last couple of months I’ve followed creative pings to try launching a founder group coaching cohort, host a corporate workshop for a client’s company and do a speaking engagement. These aren’t adding meaningful revenue to my business (yet), but they’re experiments that show me what energizes me (and what doesn’t), what I’m naturally good at, and what resonates with people. As I learn from the “MVP” of each of these, gather feedback and iterate, I know I’ll be able to monetize them more and more over time. 

6. LEARN TO WORK WITH YOUR FEAR

Everything you want is on the other side of fear. Otherwise you’d just do the things you need to do right to get to where you want right? As an entrepreneur, a major key to success is learning to work with your fear.

Here are the steps I’ve found useful myself: 

1) Get clarity on what it is you’re actually scared of. What would happen if the thing you’re scared of comes true? And then what would happen? And then what? Usually underneath the fear is an emotion we don’t think we can handle feeling. 

2) Show your nervous system it’s safe to feel that emotion. I would picture the scary thing in my head, and then follow that by coming back to nervous system regulation practices (e.g. breathing, chanting, grounding, etc.). Go back and forth between the scary thing and the grounding feeling to expand your nervous system’s capacity and show it that it’s safe. 

3) Take baby steps to build self trust. What’s the smallest step you could take to face this fear and show yourself it’s safe? Start with that and build up from there.

4) Normalize fear and remind yourself that if you’re feeling it, you’re on your growth edge and that’s a GOOD thing. No fear, no growth. So many people stay stuck on the safe and comfortable side of fear which has the hidden cost of misalignment, stagnation and never feeling fully expressed (amongst other things). If you're facing your fears, give yourself some loving encouragement because you are not settling for that and that is brave and self-loving in and of itself.

7. THERE’S NO “RIGHT” TIMELINE

As I’ve built my business over the last year, I’ve been plagued by this feeling of “being behind”. Feeling like I need to achieve ‘x’ by ‘y’ date. But when I think about it… why??? That pressure only makes me feel more stressed and more in need to control things. It blocks my creativity and intuition. It sets me up for disappointment and shame when I don’t hit these internally, randomly set goals. Which totally messes with my vibe (which is, like, pretty important for my job).

I’ve also had the challenge since burning out of navigating chronic fatigue, illness and imbalanced hormones, where I’ve frequently been forced to cancel my work and rest. Time and again that taught me the lesson of surrender, that I cannot control time. What I can do is befriend the parts of me that are trying to control my timeline. To understand what they’re protecting against me feeling. To understand their positive intentions and hard work and accept them exactly as they are. To help them feel seen and loved so they can start to relax, and so I can too.

8. EXPAND & CONNECT, DON’T COMPARE

Expand your thinking with inspiring books, podcasts, and creators. Learn from the people that make you feel better about yourself and expand what you think is possible. That shit literally rewires your subconscious, which drives your emotions, your behaviors and consequently your life. 

Find your fellow entrepreneurs, the ones who are doing the inner work, that want to make the world a better place. Who are kind, and self-aware and have the capacity to genuinely be happy for you. Entrepreneurship is hard! It helps to have people who are going through it too. To realize you’re not alone. That you’re not crazy for choosing this path. That the joy is in the creating, the journey, the figuring it out. That the lows are a normal part of the gig.

Don’t compare. Especially not to people who do not align with your values and beliefs. Maybe they have what you want, but if they didn’t get there in a way that’s in integrity for you, it’s not helpful. Limit their content. Unfollow the tech bro that says you need to hustle in a toxic way to get there. Protect your precious brain.

9. WITH ACTION COMES CLARITY 

Don’t wait for “full clarity” to start. It doesn’t exist. Clarity comes when you start before you’re ready. It surfaces as you go out and take swings, fall short, and see what hits. Momentum comes from taking the tiniest first step.

10. WHAT MAKES IT HARD IS WHAT MAKES IT WORTH IT

As much as I look back on the last year and think “damn, this was a lot less smooth than I anticipated", I’m grateful for that. No seriously I am. Because it’s forced me to get to know myself more deeply, to overcome fears, to deepen my knowledge, my wisdom and my presence. 

Looking back at how much I’ve changed and grown, I’m a whole different person than I was two years ago when I had to leave my startup. From the ashes of my burnout, Within was born. And from the struggles of my first year of business, has come the wisdom and presence that will allow me to serve my clients in ways I couldn’t otherwise. What broke me gave me my purpose, and what challenges me is what gives me depth. Both are required for success and wellbeing in my business. 

So if you’re an entrepreneur, congratulations. You’re doing something most people don’t even risk trying, let alone figure out how to succeed in. You’re learning and growing SO much and I’m so, so proud of you!!! 🥺

If you’d like some support in walking this path, from someone who is figuring it out as they go too, let's chat.

• 1:1 Coaching: I want to help you fall in love with building your company again. Book a free coaching consultation to learn how we’ll work together on this.

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

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

Thank you so much for being here with me!

With love,
Roslyn 💚