After 4+ years as an entrepreneur, here's the truth: it's not the easy solution most people think. The real upsides, downsides, and who should actually do this.
As someone who’s spent their career in startups, I have seen this time and time again. I’ve been a Chief of Staff sitting as the right hand to two different CEOs during my career. And worked adjacently with many more. I have helped build two tech businesses from the ground up with someone else’s money. Taking less in the beginning, with the same goal as everyone else later — a payout to create more freedom. I’ve also launched a housekeeping business for a friend that loves to clean who’s now working on bringing more people on because luckily for her business is booming — but she too spends less time doing what she loves now. I’ve consulted on multiple other businesses. And am working on a side project that could potentially launch my own business in the next year or so while I’m currently focused on value proposition design for product market fit through end user interviews.
But I’ve been lucky to do all of this under steady salaries which ironically is what gave me the freedom. For the most part I enjoy being the woman behind the curtain, and it comes with far less risk.
But the thing is this: I’ve watched people bang their heads against the wall trying to solve a problem, I’ve worked alongside CEOs as we’ve raised millions and millions to see their ideas come to fruition. And even then, the ideas never go as planned. It takes a village so the best thing you can create for yourself will always be leverage. In your daily life, in your conversations with clients, in the work you choose to spend time on.
Sometimes that leverage looks like automation and tools that work together, sometimes it’s a virtual assistant, sometimes it’s simply an offer that people are clamoring for. Whatever it is. Leverage will always be key in figuring out how to get the next 80% off your plate so you can focus on the 20% that will move the needle.
There’s 4 books that have been the most influential in my career (not all will be relevant but the last one definitely is):
1. Play Bigger
2. $100M money models (and $100M leads)
3. Unreasonable Hospitality
4. 10x is easier than 2x *** (this one is the one that I was reminded of during your post)
Look I’m no expert, I’ve built my career around “well that didn’t work so let’s try this and see how it goes”. But that’s all it ever really comes down to. And even the ones that seem like they have it all figured out are really just lucky to be following their gut in the right direction, and it almost never means true certainty.
But if you ever need a sounding board, I would gladly help or have a coffee chat. Good luck and I wish you high value clients in the near future!
Thank you so much for your thorough comment Sydney!
Sounds like you’ve done so much already!
Something that stood out and got me intrigued: “For the most part I enjoy being the woman behind the curtain, and it comes with far less risk.” > Do you have the curiosity or the itch to see if you could also make something work by being more at the forefront of the business? This is something that I’ve always been curious about myself… I love being in the back, but I also want to know if I have “what I takes” to do something by myself for some reasons.
I haven’t heard of books 1, 2 and 4… adding them to my list ✅
Truthfully, yes I do! For whatever reason that I cannot explain I’ve always had the crazy desire to start my own business. But I decided early to work for CEOs because there’s no better education than that. But with little experience and a big degree I started as an executive assistant so I could read their emails and worked my way up to Chief of Staff — a mix of luck, faking it til I could make it, and lots of hard work. It’s not a traditional path but I thought well if I don’t have the experience might as well read their emails all day and see how they work first hand until I have my big idea.
I had my big idea I think last year that I’ve been working on on the side but now with years working for them and my current one being so kind he’s actually supporting me as a side project — from behind the curtain — while we work on his first, maybe mine fully next.
So it’s definitely not a traditional path but provides a safety net to fail fast and pivot without much risk to my “salary”.
I totally agree with you, shadowing and doing is the best way to learn. I’ve learned so much myself in an early-stage startup, when there are no walls and you can hear all the discussions in the office… the experience you get there is so valuable.
I hope when you get a chance to work on your idea that it works out 💪
Really great points all around. Lately, I’ve been reminiscing about the 9-5 hours of my previous life with great fondness. But I wouldn’t have been able to sail the world with that setup. This is the only way I can live the life I want, so that’s a big reason why I do it. However, I refuse to trade my 9-5 for a 24/7/365, which is the reality of lots of entrepreneurs I know. So maybe there’s a cap to how much revenue I will hit or it could further extend my timeline for growth. So grateful that I don’t need to support a lifestyle in a major western city, though. I only need ~$1500/month to thrive out here :)
Thanks Cory. I did think about you a little when writing this actually considering our private exchanges.
I love your boundaries. Yes, entrepreneurship doesn’t have to be “always more”… we all have an “that’s enough money” if we are mindful of our lifestyle… and that’s when the magic happens, when we finally find this sweet spot between work and life… and can afford to chill and enjoy life without feeling guilty of not doing enough with work.
This is very well put, and I relate a lot to this. Started my own company a couple of years ago, preceded by some "magical thinking" of what entrepreneurship would look like.. reality was so hard! The financial instability I felt (I left my corporate job to pursue this) and the constant anxiety really hit me. Your article will help people put things more into perspective sure.
Exactly, especially your last sentence, that’s the reality! The best entrepreneurs are not the ones creating the best products… they’re the ones who are great at getting eyeballs on their products.
This is no joke. And you are spot on.
As someone who’s spent their career in startups, I have seen this time and time again. I’ve been a Chief of Staff sitting as the right hand to two different CEOs during my career. And worked adjacently with many more. I have helped build two tech businesses from the ground up with someone else’s money. Taking less in the beginning, with the same goal as everyone else later — a payout to create more freedom. I’ve also launched a housekeeping business for a friend that loves to clean who’s now working on bringing more people on because luckily for her business is booming — but she too spends less time doing what she loves now. I’ve consulted on multiple other businesses. And am working on a side project that could potentially launch my own business in the next year or so while I’m currently focused on value proposition design for product market fit through end user interviews.
But I’ve been lucky to do all of this under steady salaries which ironically is what gave me the freedom. For the most part I enjoy being the woman behind the curtain, and it comes with far less risk.
But the thing is this: I’ve watched people bang their heads against the wall trying to solve a problem, I’ve worked alongside CEOs as we’ve raised millions and millions to see their ideas come to fruition. And even then, the ideas never go as planned. It takes a village so the best thing you can create for yourself will always be leverage. In your daily life, in your conversations with clients, in the work you choose to spend time on.
Sometimes that leverage looks like automation and tools that work together, sometimes it’s a virtual assistant, sometimes it’s simply an offer that people are clamoring for. Whatever it is. Leverage will always be key in figuring out how to get the next 80% off your plate so you can focus on the 20% that will move the needle.
There’s 4 books that have been the most influential in my career (not all will be relevant but the last one definitely is):
1. Play Bigger
2. $100M money models (and $100M leads)
3. Unreasonable Hospitality
4. 10x is easier than 2x *** (this one is the one that I was reminded of during your post)
Look I’m no expert, I’ve built my career around “well that didn’t work so let’s try this and see how it goes”. But that’s all it ever really comes down to. And even the ones that seem like they have it all figured out are really just lucky to be following their gut in the right direction, and it almost never means true certainty.
But if you ever need a sounding board, I would gladly help or have a coffee chat. Good luck and I wish you high value clients in the near future!
Thank you so much for your thorough comment Sydney!
Sounds like you’ve done so much already!
Something that stood out and got me intrigued: “For the most part I enjoy being the woman behind the curtain, and it comes with far less risk.” > Do you have the curiosity or the itch to see if you could also make something work by being more at the forefront of the business? This is something that I’ve always been curious about myself… I love being in the back, but I also want to know if I have “what I takes” to do something by myself for some reasons.
I haven’t heard of books 1, 2 and 4… adding them to my list ✅
Truthfully, yes I do! For whatever reason that I cannot explain I’ve always had the crazy desire to start my own business. But I decided early to work for CEOs because there’s no better education than that. But with little experience and a big degree I started as an executive assistant so I could read their emails and worked my way up to Chief of Staff — a mix of luck, faking it til I could make it, and lots of hard work. It’s not a traditional path but I thought well if I don’t have the experience might as well read their emails all day and see how they work first hand until I have my big idea.
I had my big idea I think last year that I’ve been working on on the side but now with years working for them and my current one being so kind he’s actually supporting me as a side project — from behind the curtain — while we work on his first, maybe mine fully next.
So it’s definitely not a traditional path but provides a safety net to fail fast and pivot without much risk to my “salary”.
Love that.
I totally agree with you, shadowing and doing is the best way to learn. I’ve learned so much myself in an early-stage startup, when there are no walls and you can hear all the discussions in the office… the experience you get there is so valuable.
I hope when you get a chance to work on your idea that it works out 💪
Really great points all around. Lately, I’ve been reminiscing about the 9-5 hours of my previous life with great fondness. But I wouldn’t have been able to sail the world with that setup. This is the only way I can live the life I want, so that’s a big reason why I do it. However, I refuse to trade my 9-5 for a 24/7/365, which is the reality of lots of entrepreneurs I know. So maybe there’s a cap to how much revenue I will hit or it could further extend my timeline for growth. So grateful that I don’t need to support a lifestyle in a major western city, though. I only need ~$1500/month to thrive out here :)
Thanks Cory. I did think about you a little when writing this actually considering our private exchanges.
I love your boundaries. Yes, entrepreneurship doesn’t have to be “always more”… we all have an “that’s enough money” if we are mindful of our lifestyle… and that’s when the magic happens, when we finally find this sweet spot between work and life… and can afford to chill and enjoy life without feeling guilty of not doing enough with work.
Hope we both get there soon 🙏
This is very well put, and I relate a lot to this. Started my own company a couple of years ago, preceded by some "magical thinking" of what entrepreneurship would look like.. reality was so hard! The financial instability I felt (I left my corporate job to pursue this) and the constant anxiety really hit me. Your article will help people put things more into perspective sure.
Thank you Nathalie for sharing your perspective on this.
How did things evolve for you since you started a couple of years ago? Are you more “stable” now, more balanced?
Exactly, especially your last sentence, that’s the reality! The best entrepreneurs are not the ones creating the best products… they’re the ones who are great at getting eyeballs on their products.