The 7 levels of entrepreneurship (and how to climb them).
The difference between owning a job and owning a business is massive. One earns an income, the other delivers time and financial freedom. (Imagine you took a month or two off this summer. If your income would stop, you own a job.)
No one starts out knowing how to build a business. Most of us start by getting good at what we do – good enough to get paid to do it without working for someone else. Eventually, we realize there are levels to entrepreneurship, and freedom lives higher up.
As you climb the ladder from self-employed to a job-creating, legacy-leaving entrepreneur, you build skills and grow into the person who can succeed at each level.
The Ladder of Entrepreneurship
Level 1: Employee: You’re Paid to Learn
As an employee, you’ve gone from being a student and paying to learn, to being paid to learn about a business. If you’re here but ready to start climbing, this is your training ground. Your job is to learn. Get involved, take every training opportunity, get to know all the roles in the business, and try to understand what’s working and not working.
Level 2: Self-Employed: You Own a Job
After being an employee for a while, you might start yearning to start a business “for the freedom”. You dream of working when, where, and with who you want.
Soon, you’re working longer hours for less money – and wondering where the freedom went. Cue burnout.
Lots of people stop (or give up) here. About 3 million Canadian businesses have no paid employees. But if it’s freedom you’re after, you need to take the leap to the next rung of the ladder.
Start creating repeatable processes. Follow them. Figure out how to train someone else on them. Write the job description for the person who can take the lowest skill tasks you don’t want to do off your plate.
Level 3: Manager: Building a Team of Doers
With your first hires, you start to get work done through other people. Before this you may have outsourced tasks, but now your job is building competent employees. This means new systems for communication (like daily lists and weekly meetings) and consistent processes.
You’ll also need to avoid common traps about who and when to hire (it’s probably not your cousin, and it’s definitely not because they really need a job.)
Level 4: Director: Building a Team of Managers
As the business scales, you’ll no longer manage individual employees. You’ll hire or promote managers and oversee them. This means learning to get work done through other managers, orchestrating the strategy to achieve your goals. You’ll learn the art of leadership and how to steer company culture by enrolling others in your vision.
Level 5: Owner: Your Freedom Point
At this stage, the leadership team has completely taken over the day-to-day operations for the business. It’s become an asset that no longer needs your full attention and effort. You’ve built a strong team, and now you can step away and let them run the business without you. At this stage, you get to decide whether to keep it as an asset or sell it.
Level 6: Entrepreneur: Running Multiple Businesses
Once you’ve pulled back from the day-to-day operations of your business, you can consolidate and re-apply all the skills you’ve developed more effectively. You can start and run businesses without going all the way back down to the self-employed rung. In other words, you can oversee many businesses, because you won’t be stuck in any of them. Look at Richard Branson as an example. Through Virgin Group, he has an ownership stake in over 400 businesses, and he doesn’t seem to be stressed out or losing sleep.
Level 7: Investor: Your Money Makes Money
At the top of the ladder to freedom are savvy investors who make money using money, rather than their labour or ideas. The key skill here is assessing where to invest and then letting your money do the work across investment classes that could include real estate, businesses, or shares of businesses (stocks).
This Week’s Takeaway
Here’s a confession: I used to think being self-employed meant I’d made it. I’d built my first “business” doing work I liked and on my own terms. It took having a family to realize that I’d built a job instead – a hamster wheel with no benefits or time off.
Today, with training, experience, and perspective, I help others move up the ladder.
So, where are you now? And who do you need to become to reach the next level?
May 1st: A Framework to Transform Your Team
Join me in-person in Mississauga to make your job easier and your team stronger!
Register here for your tickets!
If you build the people, they’ll build the organization. Companies with great managers boast better morale, higher job satisfaction, reduced turnover, and higher profit margins.
Whether you’re new to building a team or looking to sharpen your skills, you’ll leave with practical tools to make your job easier and your team stronger. Visit the webpage to learn how and save your seat!
New Sales. Simplified: By Mike Weinberg
If you’re looking to sharpen your sales skills in a practical, no-nonsense way, New Sales. Simplified. offers solid guidance. It breaks down how to target the right prospects, craft a compelling message, and structure outreach in a way that builds trust instead of resistance. If business development is on your plate, this book provides a clear roadmap to make the process more effective and manageable!
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