Lessons from a Decade of Entrepreneurship

It’s my birthday week and this birthday marks 10 years of full-time entrepreneurship. A decade is a long time and as I ponder the future and what the next ten years will bring, I’m also looking back at some of my learning in the hopes that it can help you.

In November 2006, I walked away from my corporate job and opened a bricks and mortar retail store called Parlez Wireless. It was an authorized TELUS dealership in Ottawa. It would be an understatement to say it was the bravest and scariest thing I ever did.

To leave a good job with a great income, stock options and benefits is what some would call crazy. But to me, it was crazy to stay when I had the fire in my belly to be fully in charge of my life.

The ten years since then have been remarkable. There are many lessons that I’ve learned as I built up that retail business and then sold it, and started my own private coaching and consulting business. One of the most important lessons is the power of action.

Knowledge is what you know – Action is what you do with what you know.

As I reflect on the last ten years, I don’t regret any of the action I took. The only tiny regret I have is not making the decision to follow my dream of self-employment earlier.

I want to take some time to share with you some of the most important lessons that I learned over the years.

Lesson One: Everyone starts out broke

The first two years of running my retail store, I didn’t pay myself a penny. When I did finally start to pay myself in 2009, it was a fraction of what I made in my previous job. When you start a business, you need to be prepared to invest time, money, and a lot of sweat equity to get it off the ground. If it was easy to start and make gobs of money, everyone would do it.

The lesson here is you need to figure out how to go from trading four quarters for a dollar to generating a profit. Once you figure out how to control your sales volumes and profit margins, you can shift into a place of paying yourself and gaining control of your revenue potential.

Lesson Two: Top line revenue doesn’t equal profit and neither does money in the bank

My retail store turned over 1M a year in retail products.
That gave me bragging rights to boast that I had run a business that generated over 1M in revenues. This would be great if it weren’t for the fact that I know my business today generates more profit on half that volume of sales.

The lesson here is that top line revenue doesn’t mean your business is a success unless the bottom line yields a healthy profit. Your ability to understand your revenues, profit margins, and cash flow are critical to your success and the longevity of your business.

If your business is generating a high volume of sales and you can’t find enough money to pay yourself, you’ve either got a cash-flow problem, you’re margins aren’t high enough, or you’re spending your profits on mindless stuff that isn’t fueling business growth.

Learn the lesson of numbers quickly in your business or you’ll never feel like you’ve got any control over what happens.

Lesson Three: You’ve got to be bold and fearless

Early on in my entrepreneurial journey, I went to the eWomenNetwork International Conference and Expo in Dallas, Texas and made a decision that I would speak there some day. There was one small problem, though… They receive over 1500 applicants each year to speak at their conference.

I knew that I would have to be bold and fearless if I was going to make this happen. I enlisted some colleagues who I knew would endorse my work, and wormed my way into a private meeting with Sandra Yancey where I managed to sell my value to their organization in spite of some serious self-doubt.

After speaking at their conference for a number of years, I even became a trusted advisor to Sandra and Kym Yancey in their early years of building and using social media for their organization.

These opportunities would not have happened if I had chosen to wait to be asked.

You’ve got to push your fears to the side and boldly go after what you want.

Lesson Four: Your network can help you accelerate your business growth

The first year my store was in operation I wasted over $20,000 in traditional advertising. I know it was wasted money because that first year we asked every single customer how they found us. None of them found us from our advertising.

Struggling to figure out what to do, I started researching some networking groups in the local area. Two women took me under their wing and got me out to a Chamber of Commerce meeting and a Women’s Business Connections breakfast.

I’ll never forget that first networking event. I was so uncomfortable walking into a room filled with strangers. I felt completely out of my element. During the Chamber meeting, new attendees had to introduce themselves. As soon as the meeting ended, this one (not so very helpful woman) beelined it for me so she could tell me everything I did wrong with my introduction.

Her actions made me want to quit but I didn’t.

I kept networking even though it was uncomfortable and each time I went, I met someone new. Eventually, I had a large network of business professionals who not only did business with me but also referred me business.

When I sold my retail store in 2012, I kept my network. When you build a network and invest in relationships, you’re building something of incredible value. Never underestimate how powerful this is.

And if you’re not comfortable networking, you need to keep going anyway. You’re the CEO of your company, it’s time to get comfortable being uncomfortable. That’s where your greatest growth comes from.

Lesson Five: Act now instead of waiting for perfection

Don’t let insecurity or perfection get in the way of doing something. You’ll make mistakes (I’ve made tons) and all that matters is that you learn and improve as you go.

Too often you think that something has to be a certain way before you act and that gets in the way of you ever acting.

This is self-sabotaging your success. You delay, delay, delay and then get into victim mode because it didn’t work out.

Act sooner, act faster, and act with less fear around perfection and then act some more.

When I started The Pilot Project, it was a PILOT. A Pilot is basically a test.

This test paid off with hundreds of people having done the work in this program. When you act on your ideas, that’s when you start getting the outcomes you desire.

Sure not everything goes perfectly the first time, but it will never go the way you want it to if you don’t start.

Lesson Six: Let go of what others think

We live during a time where other people’s approval of us and our work seems to be at an all-time high. You’ve got to let that go. 

Simply put, when you decide to become an entrepreneur, it is the ultimate responsibility. You are now fully responsible for the direction of your life. When you care too much about what other people think, you’re not being the true CEO. Build your confidence and let go of the need for approval and validation from others.

Yes, it feels good, but the only thing you should care about is delivering on the things you say you will do. Worry about your customer’s approving of your work, not your Facebook friends approving of your marketing or business choices.

It can be lonely being in charge of your company. This is why I advocate belonging to programs like The Pilot Project or Profit Pods so you can get some built in accountability and support from other like-minded entrepreneurs.

Give up the need for approval. As soon as you let go of what other people think, you are really free. 

Lesson Seven: Negotiating skills matter

When you own a company you better get used to negotiating. I’ve had to negotiate the following things so far:

• Price on the sale of my business
• Reduced merchant fees
• Salary with an employee
• Pricing on products and services with customers
• Sponsorship agreements for events
• Hours of work with team members
• Pricing on goods I’ve purchased for the business

Negotiating is a normal part of business. It doesn’t mean someone is cheap or you’re too expensive. It’s a way of communicating and getting what you want out of a deal. Ultimately you always have the right to say no when someone is negotiating with you but if you’re an effective communicator, you’ll quickly learn how to negotiate based on value so you don’t have to compromise price.

Bottom line, you’ve got to be able to comfortably have these types of conversations with people and not get emotionally attached to outcomes, or take things too personally.

Lesson Eight: Humble pie only tastes good years later

Things will go wrong in your business and when they do, it can feel embarrassing and even shameful at times. When you’re in the moment, you may struggle to understand the lesson you’re meant to learn.

It may even make you want to give up on your business.  

The day I found out I owed $100K for inventory in my retail store is still fresh in my mind. I didn’t have the money to pay for the inventory and the shame I felt around being such a bad business operator was terrible.

I had to muster up some bravery though and call and negotiate my payment terms. It was terribly embarrassing to admit I didn’t have the money and ask how I could make this right.

By picking up the phone and doing this, I learned a valuable lesson about asking for help as well as managing inventory levels and cash flow in business. Today I can talk about it with ease and share what I learned but I will never forget laying awake the night before afraid to tell my husband the situation I had gotten myself into within 90 days of opening my business.

You’ll eat humble pie and you won’t like it. But if you’re wise, you’ll learn from those situations and avoid ending up in the same place twice.

Lesson Nine: It’s okay to say no

You’re a business owner, therefore you must be rich… right?

When you own a business, many people will assume that you have LOTS to give. You will likely be asked to:

• Donate money,
• Sponsor teams,
• Donate products or services to an event,
• Speak for free,
• Pay to speak (oh yes I have been asked to pay $25,000 to speak at someone else’s event)
• Have coffee so someone can pick your brain,
• Give away your products and services for free because someone can’t afford it,
• Discount your products and services,
• Advertise in various print magazines, coupon books, advertorials, or other people’s websites and more.

You can say no.

Don’t get me wrong, you can also say yes to the causes and opportunities that resonate with you and you can also say no to those that don’t.

When someone puts you on the spot and asks you for or to do something that you don’t want to do, and you say yes, you end up resentful. Instead of being resentful, you’ve got to learn to say no.

Lesson Ten: My biggest and scariest risks have created the most growth and opportunity in my life

Opening our retail store was a big scary investment and it was 100% worth it.

The first expensive online program I bought was the catalyst for my business today and has paid back dividends beyond mywildest dreams.

Spending $1000 for an hour of someone’s time, helped me increase my confidence around my own fees.

Getting on a very big stage in front of 1000 people taught me I could speak in front of any sized audience.

Firing my first client gave me the confidence to only work with people I love to work with.

Being an entrepreneur is a big responsibility. You have to be prepared to do things most people will never do in order to have a life most will never have. When you lean into your opportunity, give up caring about what others think and take massive action, you can have a really incredible life.

It takes time. Don’t expect that your #business will be an overnight #success Click To TweetIt’s taken me a decade to be an overnight success.

How long have you been self-employed for? Leave a comment below and let me know! Also, I’d love to hear about a lesson that you’ve learned from being self-employed.