10 Things I Wish I Knew the Day I Started my First Company

Debbie Madden
The Startup
Published in
3 min readNov 23, 2018

At 21, I had just graduated college and started my first job.

Today, I’m 43 and my career is in full swing. I’ve started five companies and been CEO of three of them. I’ve landed two consecutive companies on the Inc 500 list. I have experienced many successes and have weathered many failures. I have learned a lot. I’m still and always will be learning. Yet, there are a handful of truths that I’ve accumulated throughout the years that guide me.

Whether you are starting your first business, your second, third or fourth, I hope you get as much out of these lessons as I have.

These are the 10 things I wish I knew the day I started my first company:

Time is more valuable than money

As an entrepreneur, don’t make the mistake of putting off living your life until you’ve ‘made it’. Throughout your career, you will earn various amounts of money. You will never have various amounts of time. Every day only has 24 hours in it. Treasure your time.

If you don’t like something about your job, try to change it

You likely have more control over the situation than you think you do. Don’t expect every single day to be all sunshine. Entrepreneurship is hard, it’s supposed to be. Yet, if there are a few parts of your job that you don’t like, talk with someone about it and brainstorm solutions to make the situation better.

Whenever you are faced with a complex problem, don’t try to solve it right away.

First, write down the facts. Second, write down the outcomes you seek. Third, write down the problem you believe you are trying to solve. Fourth, write down at least five alternatives to solving the problem. Then, and only then, can you begin to try and solve the problem?

You don’t know as much as you think you know/

Seek mentorship from those that have walked the path you are currently walking. Speak with other entrepreneurs, with other executives. Watch and listen to those around you. You have a lot to learn.

Learn how to negotiate and then keep mastering this skill.

Whether you are speaking with employees, clients, vendors, every conversation is a negotiation, even if it doesn’t at first appear to be.

There’s more than one path to success.

Don’t fear change. Embrace it. Unexpected things will happen throughout your career and that’s ok. Your journey to success has multiple pathways.

There’s more than one path to happiness.

You’ll never know how you will feel in a moment until that moment arrives.

Stay active.

Exercise improves both memory and thinking skills, both of which are critical entrepreneurial skills. Stay active throughout the years by doing some type of exercise every single week. You might even find you do your best strategic thinking while exercising.

Read.

Bill Gates reads an hour every night and takes notes in the margins of every book. Read and listen to as many business blogs, podcasts, and books as you can.

Enjoy the ride.

You are the only one who controls how content you are with your work and your life. No matter how far or close you come to achieving your goals, enjoy the ride along the way.

Originally posted on Inc.

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Debbie Madden
The Startup

Founder & Chair at Stride www.stride.build - an Agile software development company, Podcast host of Scaling Tech