Taking Initiative: Learning “I’ll do it” and “I’m sorry”

This is a long post—one of my longest ever. I’m warning you up front because I want you to commit tolightning strikes reading the whole thing. Why? Because I share two of the most important lessons that I have ever learned, not just about taking initiative but about leading a deeply meaningful life.

I thought about breaking this post up into shorter posts that would be more conducive to the way most people tend to read online: 300-500 words with lots of short paragraphs, phrases in bold and italics, and one-word sentences.

I couldn’t do it. Or I chose not to do it. This post isn’t like every other post on taking initiative, which is the same as sensitive leadership.

It’s long, but I hope that you’ll read it anyway. I hope that it helps you do remarkable work and make a lasting change in your life.

Why wasn’t I more afraid?

After my boss told me that he had to let me go—in the middle of the worst recession since the Great Depression—the first thought that came into my head was, “At least I don’t have to cut my hair.”

I’m not making this up to add humor to this story. The Creative Director had been hassling me about my shaggy locks for a couple of months.

Why didn’t fear clamp down on the back of my neck? It’s not like I am some fearless adventurer and adrenaline junkie. I’ve never killed a lion with a spear. I don’t watch base jumping and free climbing on ESPN 17. Out of all the flotsam and jetsam of that experience on April 17, 2009 and during the two years that have passed, two explanations have bobbed to the surface:

1) Faith

I can’t remember a time when God has failed me.

I lost my job on a Friday, and on that following Monday morning, the full reality of my situation came bearing down on me like a semi with bad brakes. In the quiet of my bedroom, I hit my knees and held up all my panic and anxiety. What are you going to do about this? I wanted to know. Please, please, please give me a word to meditate on today. Give me some comfort and reassurance.

He said, “I have given you the freedom to trust me.”

Well, I guess I was hoping for a little more, but that will have to do, I thought, at the same time recognizing the truth of what He had told me.

I had $486 in my bank account, $6000 worth of debt from grad school, and a recently deceased job. He’d stripped away other sources of security and left trust as my only option, sitting on the table like a glass of cold water—refreshing but sometimes hard to swallow.  Either my faith was right and good and He would look after my needs, or it was a sham. Good times.

2) Initiative 

Richard Branson

Richard Branson

The other reason that I felt minimal fear when I was laid off and that onrushing panic and anxiety quickly subsided was that I didn’t feel wholly unprepared for my situation.

I hadn’t completed some unemployment bootcamp. I didn’t see myself as a younger, less British Richard Branson. But I had confidence in my creativity, resourcefulness, and talents, and I had learned how to take initiative.

I use those words “learned how” because I haven’t always faced my fear of failure. In my first post in this series, “Taking Initiative – Why I Was Never a Star Athlete,” I talked about my lack of athletic accomplishments during my middle and high school years. I learned that I shouldn’t take initiative if I wasn’t “good” at something. Better to pass the ball to a better shooter. Better to let somebody else try out for quarterback. Better to hang out in the outfield where fewer balls would visit and create opportunities to drop them.

Better not to hurt the team.

Tennis Lessons

I wish I had never believed that lie. Yes, I should have practiced more often. I should have practiced period. I played four years of tennis in high school without ever picking up a racquet in the off season. I’d walk back onto the court every spring carrying a couple of gorillas of anxiety on my back: Who was I going to let down? Which younger players were going to be higher seeds than I? Would I be even worse than I had been the year before?

My dad played tennis in college. He would tell you that he was never a standout athlete. He was never Lipscomb University equivalent of a Federer or Nadal, but he held his own. After he graduated, he played in a city league. He would tell you that his doubles partner was a great player and that’s why they were able to win the city championship, but I know that my dad, even if he was the less talented player, still had to hit more winners than net balls.

I played a lot of tennis with my dad growing up, and he always told me that I had a much more natural swinging motion than he did.

If I would only practice, then…

I’m try not to live my life shackled to “What ifs,” but I hope you get my point:

I may never have walked onto a grass court at Wimbledon, but I definitely could have explored my potential beyond the small improvements that I saw even though I never practiced. My body matured and my hand-eye coordination, strength, and quickness along with it.

Here’s what I’ve learned since high school: I don’t have to be the best.

I don’t have to be on the cover of Sports Illustrated. If I had taken more initiative, and said, “Hey Dad, let’s go hit some balls after dinner,” then he would have said yes.

I would have worked out some of the kinks. I would have become better at volleys, less likely to flinch or hesitate when my opponent tried to rip a forehand cross court. I may never have garnered the envy of my teammates and resented of my defeated opponents, but I would have enjoyed the pleasure of giving myself to something.

Risking Initiative

I would have learned earlier to risk initiative.

I am thankful that I did learn later. I was a senator-at-large for one semester in college before I grew bored with reallocating the money that the administration gave the SGA to spend.

During my short tenure, I did successfully lobby for continuing  financial support for Exordium, our school’s fledgling literary journal. One of the people in favor of sending the money elsewhere was the stereotypical frat daddy with his pastel polo tucked into his J.Crew khakis—I mean nothing against J. Crew—and a tendency to see only one facet of any given issue.

“Nobody reads it!” he said with a smirk and folded his hands behind his head, as though he had just identified the elephant in the room and settled the matter.

“I do,” I said.

“Well, of course, you do,” he said. “You’re an English major. But what about the rest of us? I think the money should be spent on something that has broader appeal, not wasted on something that only a few people like.”

“Do you read Shakespeare?” I asked.


“Well, I suppose we should stop printing Shakespeare if you don’t read it. We should kill the literary journal if you don’t see its value. Surely the only things that matter are the ones that have ‘broader appeal.’ Let’s cut the pursuits that make us human, like literature and the arts, and throw a fun party instead, one that people won’t even remember in six months.”

The tension in the room was palpable.

The literary journal kept its funding.

I’m not saying my logic was bulletproof. People do remember parties, and I’m not so much of a contrarian that I wouldn’t agree that some things have broad appeal for good reason.

How would the world be different, for example, if we’d never had the pleasure of listening to Creed? Life changing.

Becoming Irreplaceable

Fast forward five and a half years, and I’m working as a copywriter at a marketing firm. We need to cut expenses, and we’re paying someone to come pick up the recycling.

“Why?” I ask the office manager.

She shrugs. No one else wants to take it to the recycling center a half mile away.

“I’ll do it,” I say.

Whoopie Pies

The office manager is tired of planning the firm’s famous Christmas party year after and year. I’m farther down in the pecking order, so that responsibility falls to me. One of my tasks was to find and purchase Christmas gifts for our clients. I was all set to order hundreds of dollars worth of Whoopie Pies from Dean & Deluca when a thought occurred to me:

What if I baked miniature loaves of my grandmother’s pumpkin bread for our clients instead? I could buy nice Wilton baking pans, use all organic ingredients, and save enough money to make donations to several local charities.

I sold my boss on the idea and got to work. I did have to spend six hours baking one night after a full day at work, but that meant that Young-Williams Animal Shelter and Child & Family Tennessee received money to help animals and at-risk families.

I developed a social media package to set up a presence on Facebook and Twitter for our clients and teach them how to use it effectively over a six-week period.

I rewrote our branding strategy.

I even found out how to bake cookies in the toaster oven in the kitchen.

You wouldn’t believe what the smell of fresh-baked cookies can do for morale. Sure, the economy sucked and all of us were making less money, but how many people in Knoxville got to take an afternoon cookie break.

I began to realize that the projects I dreamed up and initiated became the ones that I most enjoyed and were often ones that met a real need at the office.

What I lacked in sports I found in business.

I also discovered that being irreplaceable is no guarantee of job security.

Beginning a Successful Freelance Career

April through July were lean months, and in August of 2009, I didn’t earn a cent.

By April of 2010, however, I had built Bright Newt, my thriving freelance business, and paid off all my debt.

Think about that: Starting with less than $500 in my bank account, I eliminated $6000 worth of debt in about ten months while working a freelance writer during the worst economy since the Great Depression.

Go figure.

I believe that this happy tale had less to do with my taking initiative and more to do with a Father who loves his children and gives them good gifts, but we can discuss faith and providence later.

This I know to be true: there’s no such thing as job security.

The only security in this economy and just about any industry is developing a certain skill set that will enable you to bring transformational value to any organization, especially one that you build.

Not all of your ideas will be golden geese. Mine certainly haven’t been. I tend to get more excited about my clients’ projects than they do, and I’ve fallen for ploys like “I want to build a partnership with you” or “I want to invest in you.” I learned the hard way that most people who feed those lines to you want your talent for free or at a steep discount. They claim to respect what you do, but don’t want to pay you the respect of paying full price. Other people really mean it and pay you handsomely.

I’ve made mistakes. I’ve missed the very deadlines that I set. I’ve even sold my services to people whose organizations didn’t have soil rich or deep enough to grow anything with my best work.

At times, I haven’t fought for truly potent writing, ideas, and marketing strategy and allowed clients to move forward with neutered initiatives.

You can’t do everything and do everything well. You have to choose. You have to say no. You have to stand up to your boss, and you have to stand up to your clients. You have to take responsibility for your mistakes.

What’s even more difficult is refusing to be passive and take responsibility for a client’s mistake. They’re human too, and they aren’t always right.

I’ve taken initiative and then done the minimum to honor that commitment and protect my reputation as a creative professional. But I knew that I could have done more. I could have made room for someone with more energy, time, money, or love to give.

“I’ll do it.”

Let me share one final story before I make my way out of this long post.

I was hired to write website content for a sales training and recruiting coaching business in Knoxville. The two men who own and run SalesManage Solutions are at the top of their game. Lance and Steve can save their clients hundreds of thousands of dollars a year by teaching medium-sized and large organizations to stymie the blood loss that comes with high turnover and unproductive sales teams.

They were relaunching a web-based sales funnel management app (salesactivities.com), and they hired me to write content for the website.

Lance had been making notes on a huge white pad, and in a moment of clarity, he turned to the four of us, including Steve, the developer, the designer, and myself. He said, “We need someone to quarterback this thing.”

The project had bogged down because everybody was doing his job, but no one was calling the shots. I was the youngest person in the room. I had the least business experience. I had already finished the writing, but because I had been a part of the larger conversations, I was invited to the meeting.

I was the least likely candidate to give marching orders.

taking initiative

“I'll do it.”

But I took initiative.

“I’ll do it,” I said.

I could see everyone relax: “Phew. Someone is taking charge. Someone will make sure that this gets done.” For reasons beyond my control, we missed our first deadline. I apologized to the team anyway.

We nailed the new deadline.

Taking initiative begins with having the audacity to say, “I’ll do it.” Finishing well sometimes requires saying, “I’m sorry.”

I’m no adrenaline junkie or billionaire entrepreneur, but I’m doing work that I love because I learned how to take initiative.

You can too.

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