Keep Climbing

What I learned from failing to reach the top of my biggest professional mountain to date

Hey, it’s Alexandra. Welcome to my weekly newsletter where I share my latest reflections on professional development and well-being.

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This week, I share what I’ve learned from:

• Launching and failing in business

• Climbing my “Everest”

• Redefining success

 ☕️ Read time: 5 mins (best with tea or coffee)

Views of the Southern Alps in New Zealand back in July 2018

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“One day, the mountain that was in front of you will be so far behind you, it will barely be visible in the distance. But who you become in learning to climb it? That will stay with you forever. That is the point of the mountain.”

—Brianna Wiest

It's been eight months since I quit pursuing my dream.

My biggest motivators for becoming a solopreneur were freedom, flexibility, and continuous learning. From having the power to choose the projects and clients I take on to being able to work from the city or country (or evade Canadian winter by spending a few months down south), I wanted more capacity to embody my ideal lifestyle.

I also wanted more control over my schedule.

I wanted to avoid the constraints of a typical 9 to 5 where you need permission to go to a doctor or dentist appointment, take a midday fitness class, or attend a family event.

The latter became more important to me as I began thinking about kids.

I wanted to give future me the freedom and flexibility to spend as much time and be as involved as possible with my kids’ school stuff and extracurriculars when the time comes.

I also wanted to challenge myself to grow and expand.

So I took my shot at solopreneurship and gave it everything I had for slightly over two years.

Unfortunately… it didn’t pan out.

In today’s edition, I’ll break down why. Plus what it taught me so you can avoid similar heartache.

What I learned from climbing my biggest professional mountain to date

1. I learned freelancing isn’t for me

Like most newbies, I had an idealistic view of what freelancing would be like.

But when the novelty wore off, reality sunk in.

Freelancing began to feel like a job without benefits.

Sure, I had more freedom and flexibility regarding how and when I got my work done. But I felt like an outsider when the teams I was working with shared a sense of belonging, additional projects, and inside jokes.

I started feeling lonely.

So I decided to make a change–which brings me to point #2.

2. I learned my ideal co-founder would be a marketing machine

Can confirm per my ski trips to the French Alps in 2019-2020 that mountain adventures are best enjoyed with friends.

I decided to launch a course-based community.

Things started off well. I was able to fill my first cohort through my network and I helped some great members launch courses.

But when my intake petered out, I was at a loss for how to market my offering.

I wished I had a co-founder to guide me through that side of the business.

So next time I launch an offering, I’ll know what type of partner I need to give it a chance at thriving—which brings me to point #3.

3. I figured out my unique offering

When I first started my self-employment journey I described my work as “helping people package their expertise into educational products such as courses, workshops, templates, and content.”

But then I learned two things about pitching.

First, you have to speak to the impact you create for others, and second, you have to be specific about who you serve.

So I revamped my pitch as follows:

I work with founders/CEOs and their companies in two ways: 

1. I help them create courses and educational content to become thought leaders in their industries.

2. I help them replicate the skills of their best employees so others can get to their level. I analyze how they do the job, identify what makes them excellent, and turn my findings into training and best practices.

Likewise, I used to say my differentiator was “Most people working in the online course creator space do marketing or operations but few know how to build pedagogically strong courses. I can help experts create effective courses that don’t put their reputations at stake.”

But when a marketer friend encouraged me to dig deeper, I asked past clients why they chose to work with me and they expanded on the above with the following:

• I provide a rare combination of warmth and empathy with the discipline to get stuff done.

• I create autonomous workflows so they can do the bulk of the work on their own which saves them a lot of time, money, and energy.

• I care and show my investment in co-creating with them.

Now that I have these insights, I’ll be more confident communicating my value in the future.

Now finally, let’s jump to point #4.

4. I burnt out and emerged better for it

Montreal native Leonard Cohen famously said, “There’s a crack in everything, that’s how the light gets in.” (Photo source: Marcus Restaurant)

There’s a saying that “You can't open your heart fully until it's been broken.” Whether it’s the end of a relationship, the loss of a loved one, or some other painful ending, by putting the pieces back together, you develop a greater capacity for love.

The same can be said for burnout and the realization that something you’ve worked extremely hard at simply isn’t working.

Succumbing to my extinguished flame and the fact that all my hard work, sacrifices, and investments had not yielded my desired return broke my heart.

It was a painful ending I had wanted to avoid.

But in mending the pieces back together, I came back stronger and wiser in my ability to understand my mistakes and how to avoid them in the future.

I now have a greater capacity to empathize with others experiencing burnout, crushed dreams, or other heartache—and an optimistic outlook to help them through it.

Redefining success

I stopped climbing my solopreneur mountain because the peak was nowhere in sight and I was no longer having fun.

But I still ascended to a new place. 

I established myself as an expert in my domain, built an incredible network of entrepreneur friends, and learned a TON about myself and how to run a business.

Plus I started writing and sharing my ideas online.

So when the time comes to have kids, I’ll have more options based on who I became during my climb.

And as Brianna Wiest would say “That is the point of the mountain.”

I hope whatever mountain you’re climbing is equally transformational.

Thanks for reading and have a wonder-full week,

Alexandra

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