Making Your Business Work For You

Last modified on April 25th, 2018

One of the hardest aspects of being a business owner is being able to come up with a metric, even an internal one, for what it means for that business to be successful. For some people, that goal is completely monetary – i.e., if they can sell the business for 1 million dollars within 10 years, then that represents success for them.

Making Your Business Work For You

As an example, one of my good friends recently sold his business. While it was always his dream to build a popular retail business, at some point he realized that the excitement, and the dream, mostly involved building a business, and not really running one. So even though the business was turning a monthly profit (which for some people would amount to owning a lifelong lifestyle business) he decided that it met his own definition of a successful business, at which point he sold it and cashed in on the business’ worth.

Most people are brought up believing that success in a business can only come about by perpetual growth and by increasing revenue year after year. But what’s often lost in those examples is the increasing stress that’s involved with owning and managing a large company. In addition, as a company grows, people tend to become more specialized, and that often means that your role, as an owner, will shift away from doing work towards supervising work. And depending on how you obtain satisfaction in your business, may essentially represent a demotion for yourself.

I know personally that I much prefer doing work as opposed to supervising work – that is, I’d much rather be hacking out code to build a product or a website than having group meetings where I instruct others how to. So for me, growing into a large business, one where I move from a software engineer to a product manager, isn’t that appealing to me.

What is appealing to me is owning a business that gives me the freedom to travel the world when I want or to take a four day weekend when I want. While most people don’t have that luxury (at least not initially), it’s not that difficult to obtain, as long as you plan for it – envision the lifestyle you want, then work backwards and figure out how to change your business to make that happen.

For example, if you want to be able to take a four day weekend whenever you want, you need to have a business that doesn’t have excessive daily requirements (such as 24/7 customer support), or must ensure the proper employees/co-owners are available to handle things while you are away. And sure, you may end up making less money if you have other people on the payroll, but that’s the tradeoff for having increased mobility and flexibility.

Regardless, it’s important for every business owner to actively design the lifestyle they want, and then create (or evolve) the business to satisfy that lifestyle. And as part of that, you need to define what success means in your business, and in your life. Every once and a while, perhaps every three to six months, sit down and evaluate both your business and your life. Ask questions like “Is my business satisfying my financial goals? Is it satisfying my personal goals? Is it leading me towards the type of life I want?”

This process is iterative, so don’t expect to get there overnight. But if you methodically build or adapt your business and have a clear vision of what success means to you, it shouldn’t take too long before you have a business that’s moving you further towards where you want to be in life.

One of the mantras I’ve adopted over the last decade, and one that helped lead me to successfully selling my last company (in addition to traveling to over 39 countries) is this: my business should always be working for me, not the other way around. What that translates into is always make sure my business is satisfying my life goals, and iterating with changes whenever it stops doing that.

So my advice is this – sit down with a pen and paper and design the life you want, then work backwards with your current business, or even a new business, and figure out all the steps to get you there. Imagine it’s a road trip, but instead of heading camping or to the beach, your destination is the future (and the life you want) and you need to determine all the stops along the way. Even the longest journeys begin with a single step, so there’s no better time to start planning your future than today.

If you need any additional advice, feel free to drop me a line. I can also be found on Twitter at

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