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Should You Begin Your Career by Starting Your Own Business?

Micheal Dell, Oprah Winfrey and Steve Jobs are all examples commonly used. In reality, though, these are the 1% that took this path and saw success from the decision.

Is it the best idea to go directly from education into starting your own business? What pitfalls are there?

Today we’re going to look at why I don’t advise my coaching clients to start a business before they’ve spent time working for someone else in their field.

Learning from others’ faults.

The biggest thing you’re going to get by starting your career in the employ of an established company is the learning experiences they will provide, directly and indirectly. If you’re a developer or designer, you’ll get to work in close collaboration with others in your field. You’ll get feedback from the peers who work around you. This feedback will accelerate your growth into the professional you want to be.

Yes, you can get some of this via colleagues that also own their own company. You can interact with them on Slack or Twitter, but it’s never quite the same as a fellow employee reviewing your work. Working for someone else will also give you lots of examples of how you never want to run your business.

You’ll work long hours sometimes and swear you’d never make your employees do the same. You’ll see the owner’s children get handed a role in the business and resent when they get treated differently. You’ll promise yourself that if your kids work in your business, you’ll never treat them like a unique flower, they’ll be another employee. 

Learning from others’ attributes.

I saw a customer service mentality that blew me away while I worked for Western Canoeing and Kayaking. We had one customer that bought a boat and simply didn’t like it. He was always kind to staff and came back over the course of a year to try purchasing something he loved. We gave him free lessons, and demos with the boat’s designer, but at the end of the year, he wasn’t happy. The owners gave him 100% credit on the boat towards something new.



He never asked for that and was willing to trade it in and get some reduced credit, but the owner’s just wanted him to have the boat that suited him. He walked out with a kayak he loved, and we had a used boat we sold for 50% off in our inventory. The lesson came over the next year as he brought five different friends into the shop who all bought from us with no price haggling. Western built a customer for life, and a walking advertisement for less than $500 and I learned a valuable lesson about serving clients.

Perks that can set you up for success when starting your own business.

While there were some things I didn’t love about working for 10up (and trust me, I was an unsatisfactory employee there—-we didn’t fit), I did get to spend a bunch of time working with leading WordPress developers. I got to work for huge clients that I would never have been able to land on my own. 

This experience with big clients later made it much easier to land my first Fortune 500 client a few years after I left 10up. I am forever indebted to 10up for the corporate experience I got while working there.Without all of these different experiences building into my life as a business owner, I’d have many more mistakes to make before I was able to get to the success that I have now.

The biggest mistake you make as an employee dreaming of owning your business is using your time poorly. You don’t take advantage of the lessons available.

Use your time as an employee effectively before starting your own business.

Showing up to work and punching the clock is a waste of your day. Oh sure, you collect a paycheque, but if you want to build a business, then you need to be more intentional with your time. You can’t afford to put your butt in a chair for the required 8 hours and call it a good day. You need to network. Find those in your work that are further along than you are. Find ways to get to spend time learning from them.

Not only will you have a mentor, but some of these people will move on to other endeavours and remember you. They’ll call you when something awesome comes along and want you to join them. Networking is wasted effort though if you don’t do your job well, no matter how much you hate it. None of those you interact with will happily call you for awesome future opportunities if you dragged your butt around all day.


When they see you they’ll remember how much time you wasted, and be glad they don’t have to deal with you anymore. Finally, make sure you take advantage of any learning opportunities offered. If you have a budget for personal improvement, use it. If they have a subscription to Lynda or Treehouse, use it. Even if it’s on your own time, use it. Your next job may not provide those opportunities. Take advantage of every one you can while you have it.

While we love to aggrandize the story of the successful college dropout or wildly young entrepreneur, we only hear the few stories of those that happened to luck out into success. By using your time as an employee well, you can save yourself lots of pain when the time comes for you to head out on your own and run your business. By applying what you’ve learned while working for others, you can increase your chance of success.


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Curtis McHale

Curtis McHale

Curtis McHale is a business coach and speaker. He helps businesses build effective processes for vetting ideal clients and building a business that doesn’t take every hour of every day to run.


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