Shortly after I left my corporate job to strike out on my own, a friend called to invite me on a week-long vacation. Instead of excitement and anticipation, the idea of the trip gave me immediate anxiety.

There was no way that I could completely step away from my business for an ENTIRE week – there were too many key business operations that I was involved in, too many aspects of the “day-to-day” that I was responsible for, too many risks to the business if I wasn’t around to put out fires.

Even though I was my own boss, I felt more tied down than ever.

I had to tell my friend that I couldn’t go. As I hung up the phone, I had a moment of realization. Enough was enough! What was the point of having my own company if not to create MORE freedom for myself, not less?

I decided to steer my company in a direction that would allow for it to whirr on if I were to want to take a vacation, without burning my candle at both ends until I was nothing but a puddle of wax.


I decided to work ON my business instead of IN my business.

Now, a few years later, I am the proud co-founder of Lifehack Bootcamp, an online productivity bootcamp for professionals who want support reprioritizing and organizing their lives from the top down. We’ve had hundreds of people from a range of different industries graduate from our course, and our alumni are on track to save a combined total of 100,000 hours this year alone. But best of all, the business has been designed to continue operating smoothly even in the event of my extended absence.

After tripping and falling many times, here are my key takeaways for anyone who wants to get a leg up on creating the kind of business that unshackles the owner and creates freedom:


It is a game-changer when you can start to look at your business as a web of functioning systems. Everything that you and your employees do can be simmered down into mechanical systems with ordered steps. Creating these systems is the key to gaining access to the freedom you so dreamed of when starting your own business! For example: it would probably be easier for you to do some of the day-to-day tasks that keep the business running (for example, bookkeeping). But taking a bit of time to standardize these tasks and delegate them to an employee frees up time in YOUR day to focus on ways to improve and expand the company.


Perfectionism killed the cat. Expecting your business to reach perfect functionality overnight will (ironically) cloud it’s path to success. Peak performance in a company (organization, group, project, anything really) takes time, patience, effort on everyone’s part. What’s more important – and realistic – is to create good systems and ways of working that will pay off in the long run. Excellence is in the continuous improvement of these processes.


“An ounce of prevention is worth a pound of cure.” It’s simple: since you’re the boss, it’s up to you to anticipate what could go wrong and plan ahead to prevent it. Taking the time when your business is new and full of momentum to create, document and implement precautionary measures will save you later on. I draw inspiration from pilots, who are masters of pre-planning. Pilots must know exactly what to do in the event of any number of issues. To prepare themselves for worst-case-scenario, the pilot will drill the entire flight crew relentlessly until the protocol is second nature. Now, I’m definitely not saying that the mental models you’ll be creating for your business are quite so extreme, but anticipating potential scenarios and training your team in how to appropriately react will take a huge weight off your back.


I’m a professional “worrier”, and nothing is more frightening to me than having errors happen under my watch. But taking a step back and allowing my employees the space and trust to do what they’ve been trained to do was a critical part of this whole process. Trust and inspiration are two of the most valuable things you can express to the people working with and for you. And once you see they can operate just fine without you, those worry lines on your forehead will melt away.

It definitely hasn’t been easy. The road has had a few bumps, and everyday my business faces growing pains. But as I build and re-building my business, these takeaways prove their worth over and over again.

And today, I’m writing this post from the deck of a sailboat. For the last two weeks, my friends, my husband and I have been sailing Croatia, a dream of ours for the last few years. My business roars on in my absence, requiring little, infrequent maintenance on my part.

So to those of you who are committed to start working ON your business, not IN it, I applaud you. It is well worth the effort.

And for those of you interested in learning more about dialing in your productivity and working ON your business not IN it, check out our free course here.