9 Years to Reach $100k — why it took so long, how I did it, and what I learned

Stephanie Wasylyk
5 min readJan 31, 2022


My first photoshoot, 9 years ago

Am I ready to write about this? I’m not sure. Am I sick of hearing B.S. rhetoric of instant financial success? Absolutely. So here it goes.

The coveted $100k year. For most entrepreneurs, this is the milestone they aspire to. They speak it in affirmations, they visualize it on their vision boards, and they declare it in their goals. I’m not into affirmations, but I’m totally guilty of writing it as a goal, many years in a row.

And while you’re waiting for it to happen, there’s embarrassment that you haven’t reached it yet. There’s frustration, too, because of all the glossy pictures of others who have hit their financial stride. And the ads…oh, the ads…how many do you see on a daily basis declaring if you just do things their way you’ll hit $100k this year. (It can’t be just me that gets those!)

Today is my confession. Today I get real and vulnerable with you.

Before I do, remember this is MY story, and it probably doesn’t look like yours. I made my own choices, I had my own privilege that got me to where I am, and I want you to remember that there isn’t one magical way to build a business.

So here’s the truth…it took me 9 years as a full-time coach to reach $100k in revenue.

Why did it take so long?

The better question to ask is “how long does it normally take for someone to advance to $100k in their career?” No one asks that. It’s just assumed that entrepreneurs should make more, faster, than other more traditional jobs. But the truth is, had I continued to work at BlackBerry for the last 10 years (without getting laid off), maybe I would reach it, but maybe not. More people than not never reach $100k in their lifetimes.

But it’s all about frame of reference, so as an entrepreneur, why did it take me so long?

Because for the past few years, every time I got close to making $100k, I butt up against my values. Just as I would get close, I would abandon ship. I was working too many hours, or I was working with a client that didn’t align with my values, or I was doing work I wasn’t excited about. So instead of pushing through to hit my target, I pivoted. Over and over and over. Every year, I fell short of my goal.

But every year, I got closer and closer to living my values.

How did I do it?

A big part of my business model has been working as head coach or associate coach in other businesses. They bring me in, and I coach their clients. It has been fun to work with teams, rewarding to help such a volume of clients, and educational to see behind-the-scenes in so many large companies. I appreciate each and every one of them.

Yet this leaves me vulnerable to big dips in income when those contracts end. I learned years ago not to have all of my eggs in one basket, but it’s still a disruption financially transitioning between them.

This year I was not expecting to reach it. I had a great Q1 and Q2, but then my biggest client and I parted ways, leaving major shortfalls in Q3 (which was summer so I enjoyed the time off) and Q4. But lo and behold, it still added up to $103,141.

I should also confirm that I did this working roughly 20–25 hours a week, consistently taking Fridays off.

I’ve decided not to work with any new large clients and focus instead on helping people privately, 1:1, so I truly don’t know if I’ll be able to have two $100k years in a row as I build that infrastructure, but a lot can happen in a year!

What did I learn?

There are a few key lessons that I’d like to share with you, and they might not be what you expect.

1. $100k means different things in different countries. I realized I had been striving for this number, but had never stopped to consider the value it has in different places. I live in Canada, so I know my tax rate is higher here than in the US, yet lower than in many other places. Making $100k does not mean keeping the same amount in all countries. So why have I been measuring my success based on a different country’s numbers? No idea.

2. I thought I would be more excited. I thought it would feel better. I thought it would be enough. Yet, I ended the year with a feeling of lack. Maybe it’s that things cost substantially more now. Maybe it’s lifestyle creep. Maybe it’s just my mindset and perspective. All I know is, right now, it doesn’t feel like the big win I thought it would be.

3. I didn’t realize how important my values were to me. I’m the main income-earner in my house currently and I have a young daughter, so there are lots of reasons I could have strived to earn more. Yet, leading by example for my daughter, and having the time to spend with my family often took priority when I was making tough decisions. In those moments I always had a mindset of abundance and optimism that things would work out so I was able to take leaps despite the risk on paper.

What next?

I’m absolutely terrified to share this story with you. I fear it might make me look bad. I fear it might have clients think less of me. I am a business coach, after all. Shouldn’t I be a wild success like everyone else we see online?

What I hope is that the people who want to work with me see that there’s a way of doing business that doesn’t turn you into a workaholic. A way that truly does align with your values. A way that is fulfilling and fun, and ultimately, one that is full of meaning. I do my best to lead by example, so my clients can see what is possible for them. It isn’t always a financial reward. Most of my clients already make well over $100k, but they’re working way too many hours and want more out of life. They have the money, but they don’t have the ease. I hope this is a breath of fresh air in a sea of polished exteriors and heightened expectations.

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