Lately I’ve seen so many feel-good quotes about how failure is just a stepping-stone to success and how we all have to be willing to fail faster and more often.

hogwash

The few times I’ve REALLY failed, have been so soul-crushingly horrible that I’m still scarred. Each took me months to recover from let alone start to learn what went wrong and what I need to change so as to never repeat that same mistake. That said, a painful and in-depth analysis of what I did wrong in each of those circumstances was crucial to success the next time around.

Bill Gates said it best.

“It’s fine to celebrate success but it is more important to heed the lessons of failure.”

Bill Gates

And there were definitely lessons to be learned

For me, and perhaps for others, the biggest failures came early in my career. That’s when youthful success combined with hubris led to overconfidence and a lack of preparedness. A volatile mix that leads to disaster.

Read on below for 3 of the biggest mistakes I made as a young start-up.

1. Hubris, youth and believing my own hype

I had extraordinary success early in my career. Even without social media, I became a well-known expert in youth marketing and emerging cultural trends.

I was on a hot streak including on the speaker circuit. My phone was ringing off the hook.

It went to my head.

While I started out undercharging for my presentations which were always praised for bringing a fresh new perspective and for being extremely entertaining, I was soon overcharging and under-delivering.

I also went from flying economy to demanding business class. I’m mortified just thinking about it. Of course, the work dried up and I was left wondering how I could make amends.

How I got back on track: I refocused on providing value, I really listened to my clients. And I no longer took anything for granted. I came into every situation prepared. I dialed up my skills, took classes in public speaking, sought out feedback on what worked and what needed improvement. And I used my own miles for flight upgrades.

Lesson: Stay humble. Don’t be an asshole.

2. Too much cool-factor, not enough substance

I pioneered the move away from traditional focus groups to a more ethnographic approach including in-home interviews, expert interviews and in situ observational research. Clients loved this new approach but after kicking it off with a bang, I failed to deliver consistently. I thought it was more important to recruit super cool kids versus my clients’ real and potential consumers. While it was a great experience for some clients, for many it didn’t work out.

Of course, it ended badly and again, I needed to reevaluate everything I was doing. I learned my lesson but it was harsh. Some clients (rightfully) never came back.

Fortunately, I was able to reinvent what we offered and, most importantly, become a master planner and rarely, thereafter, missed a beat when it came to recruiting spot-on consumers and experts.

Lesson: Listen and then listen some more. Your client is your #1 priority. And if you don’t want to (or can’t) deliver what is required, don’t take the job.

“Success depends upon previous preparation, and without such preparation there is sure to be failure.”

Confucius

3. Not paying attention to my gut about client fit

This is a huge issue for many smaller companies. After taking on clients that I knew were not a good fit (but they wanted to work with us and a lot of money was being offered), I created a non-negotiable rule for myself: only take on clients with whom I’d want to have dinner.

That was a gamechanger for me because it clarified who would be great partners. People who I want to have dinner with are also the people for whom I would gladly go above and beyond to get the job done. Likewise, I want to know that my clients have my back if anything should unexpectedly go awry.

The key is to ask lots of questions about the true expectations around all projects. I recently had an experience with a wonderful international company that went sour because I had not dug deeply enough into what they were, in fact, wanting from me. It turned out they really needed a wordsmith, not a trend expert. I felt miserable because I had disappointed this wonderful client. The whole thing could have been so easily avoided had I asked enough questions and been brutally honest with myself about what I heard and if I could, in fact, deliver what they wanted.

Lesson: Ask questions and be crystal clear about what they want and whether you can deliver it (no matter how fabulous the project sounds or how much they seem to want you).

Bottom Line.

Failure is a bitter pill to swallow. However, gut-wrenching failure is the best teacher. It makes you sit up, pay attention, and make essential change. I’m not sure what I’ve ever really learned from success (other than it feels great!).

At the end of the day, the three biggest lessons I’ve taken away from a lifetime of running my own business are 1. to be confident without being cocky, 2. there is no such thing as too much preparation and 3. always remain as grateful for hard lessons learned as you are for successes.