15 Lessons Learned in My 15 Years of Business

Starting a marketing agency was my own quest for clarity. I thought leaving a decent, but bland, career at Motorola after seven years would be exciting and make me rich like my friends who left for Silicon Valley to join startups.

While I hit the end of the bubble and made a bit of money with options, I was certainly not wealthy. By my early thirties, I was burned out. I had climbed through five companies and struggled through a divorce. I worked so many hours at one startup, the CEO would come into my cubicle and tell me to go home. Despite my efforts, I was consistently passed over for VP roles because I was “very competent, but too young” only to see the jobs go to empty suits who butt-kissed the boss. In my last startup, I found out the CEO hired me away just to get back at his cross-town rival, not because I was talented or needed. They put me in a cubicle with nothing to do (which for me, is worse than not paying me). People who knew me said the light had gone out of me – and that was truly scary.

On a bus commute to the “non-job” during the winter of 2000, I decided it was time to do something different. Creating a company in which people loved to work and felt respected was my new mission. On April Fools Day 2001, I started a journey that, other than becoming a mom, has fulfilled me more than any other endeavor. I quit my six-figure job at a tech startup and started Clarity Quest Marketing.

So for all you would-be entrepreneurs, here are the top 15 lessons I wish I could have shared with myself 15 years ago. Although these are very personal, I hope a few resonate with you.

1. Chase your dream, not the money.

For the first 10 years you will make less than you could have working for a company. However, you will be able to work part-time when your daughter is born, you will have Fridays off until she’s five, and you will be able to pick her up from school each day you’re not traveling. And you’ll never have another threatened jerk slam a boardroom door in your face because you’re female.  You will get to work with exciting, interesting people and learn something new every day.

2. Tell anyone who’ll listen about your business.

Don’t be embarrassed to tell friends, families and strangers at bus stops that you are looking for clients. ALWAYS have a business card – yes, even on baby stroller runs. You’ll find 3-4 people who love startups and believe in you so heartily; they will refer clients and build your business. Be eternally grateful to those folks.

3. Know the value of your services and time.

When prospects start to complain you’re expensive but still talk to you, you are probably priced just right. You’ll work harder than you ever did when employed by someone else. Value that effort.

4. Fire bad clients early.

The toxic ones will suck all your energy and creative spark. The money is not worth it.

5. Having to move four times in seven years will GROW your business.

While you’ll leave your innovative techy peers in Seattle, you’ll meet unbelievably creative and loyal cohorts in Ann Arbor, Michigan, you’ll learn to understand a different part of America in rural Oregon, and you’ll go back to your East Coast roots and join a small business community in Connecticut. And thanks to technology, remote team coordination will work just fine.

6. Have a cushion to survive economic downturns.

2009 will be painful…but you will come out stronger because you had a few loyal clients and savings.

7. Have a vision of who you are and who you want to be.

Don’t get distracted chasing opportunities outside your core competencies, even if they involve lots of dollar signs. Focus and a goals framework will lead to success. Don’t worry about a full-blown business plan, but know what you want to be when you grow up.

8. Some people won’t like you and that’s OK.

Competitors, employees and partners won’t always like you or what you do. You’ll annoy some people, but in the end fairness ranks above likability.

9. Hire employees smarter than yourself.

Encourage those who don’t always agree with you to voice their opinions. Accept that just because it’s not done your way, doesn’t mean it’s wrong.

10. You can’t be an expert at everything.

Don’t try to design your first website and logo yourself. Embarrassing records of those things live forever (see below). Hire a designer, a bookkeeper, an accountant and a lawyer.

11. Employees can’t read your mind.

Document everything. Record processes. Buy and implement a sales CRM and project management system early on.

12. Never send an email that can be misconstrued.

Be old-fashioned. Pick up the phone or meet in person. You’ll avoid dozens of headaches.

13. You can’t be buddies with your employees.

You are their boss, not their friend or their parent. You can think they are super interesting people to hang and create with. You can get sloppy drunk with friends. You can’t do that with employees and expect them to look at you the same way on Monday morning. Find friends outside of work.

14. Delegate prolifically.

Provide the vision, framework and processes and then let the team run. Just because they do the little things somewhat differently than you, doesn’t make it wrong.

15. Go on vacation and be totally offline.

The walls won’t come crashing down if you don’t check email for a week. You’ve surrounded yourself with amazing individuals who can handle any situation. Take breaks and don’t feel guilty. You’ll be far more creative when recharged.

It’s been a crazy 15-year roller coaster with many more ups than downs. If you start an entrepreneurial journey, I hope it will be as fun and rewarding as it has been for me. Thanks to all my clients, clients-turned-friends, supporters, partners, mentors, cheerleaders, friends, contractors, employees, and my WPO “advisory board”. Finally, I could not have accomplished so much without the support of my husband and daughter who had to share me with this corporate “child” many nights. I love you both.

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