How to use milestones as the secret to your success.

If you are not careful, your life will pass by in a flash. Your career will be over in a snap. Your kids will be grown and will have flown in a Blink-182. Because time is a crafty thief that lulls you into someday thinking. Like Sugar Ray. And then it yanks that someday away just like your prankster friend, pulling your chair away just before you’re about to sit on it, Potsy.

Milestones

One of the great ways to create a far more enjoyable and successful life and create memorable experiences is to utilize the power of milestones.

Milestones are those moments on the calendar that humans have made to mark the passage of time. Those days or events offer valuable markers for accomplishments, challenges and traditions. They are there to host rites of passage and other memory-making events. And without milestones, Hallmark would have a hard time selling you paper.

You know the big and obvious milestones. At Halloween, you dress up in a costume and do candy things. At Thanksgiving, you gather with family or friends, feast, and get thanky. At Christmas, you exchange gifts, eat, drink and praise Mary. At New Year’s, you celebrate and create lists of how the next 2 weeks will be different.

Deadlines and Opportunities

But milestones also create deadlines for accomplishments and opportunities for memorable experiences.

I sit down to write every morning by 6:10am. But Tuesdays and Thursdays are milestones to publish blog posts. Every 3 weeks, I publish Adam’s Good Newsletter. And every five years, I want to publish a new book. Those are all random and arbitrary deadlines. But they become useful milestones that make my elective activities time-bound. Milestones offer navigational markers on the naked landscape of time. Which ramps up your self-imposed productivity.

I had a major speaking event yesterday, and I used it as an opportunity to get in better shape. I committed to doing 30 minutes of cardio every day for 30 days leading up to the talk, so that I would look and feel more fit on stage in front of 1,000 people. (And I requested to have no cameras in the venue, because the camera adds 10 pounds.)

I always use my birthday as a motivating milestone. I’ve also used class reunions, New Year’s Eve, and the birth of my children as important starting points, end points and exclamation points.

I have used milestones to gain traction towards health and fitness goals, to measure my business success, and to create deadlines for my entrepreneurial launches. (Which are a lot less launchy than Elon Musk, Richard Branson or Jeff Bezos’ entrepreneurial launches.)

I used the end of the COVID-19 lockdown in 2020 as a milestone to finish the first draft of my manuscript for my first book, What Does Your Fortune Cookie Say? Then I used Thanksgiving of 2021 as my milestone to publish the book. I made both of those goals happen, thanks to the power of milestones. (Since then, I have learned how to write a manuscript without a worldwide pandemic.)

I use milestones to schedule big travel. For my wife Dawn’s 40th birthday, I surprised her with a trip to Europe. We scheduled a trip to Europe in the summer before my daughter Ava’s senior year of high school. We realized that the milestone provided the last summer opportunity for us to all travel together before college obligations made summer travel problematic. Using milestones is one of the best ways to visit the big places on your life-travel list. (Using airplanes is the other best way.)

I used a milestone to plan a major move. My wife and I wanted to find a place where we could settle to allow our children to finish their schooling without moving by the time my daughter Ava entered middle school. We moved from Atlanta to Mequon, Wisconsin, a large-yarded, low-taxed, great-schooled northern suburb of Milwaukee that sits on the Western shore of Lake Michigan. We called this our 13-year home. Which meant that we would stay in Milwaukee for 13 years, until we hit another major milestone: our son Magnus’s high school graduation. Then Dawn and I are free to hit the road again and take on more adventures.

Key Takeaway

Your greatest ambitions, experiences and traditions are far less likely to happen if you don’t tie them to a milestone. Use those special days to inspire your work, to create deadlines, and to force urgency. Use them to create regular events to bring your people together. Or to reset your ambitions, spark your goal setting and help you accomplish more elective activity than you could without them.

*If you know someone who could benefit from this message, please share it with them.

+For more of the best life lessons I have learned, check out my book, What Does Your Fortune Cookie Say? from Ripples Media. And consider subscribing to Adam’s Good Newsletter.

How in the world do you schedule your time?

My daughter Ava wants to work at The Weaponry. She is 12. While a 12-year-old may not seem like a valuable asset to an ad agency, she is a really great writer and a very creative thinker. She has a blog, she has adapted a novel she read into a screenplay, and is currently writing a murder-mystery chapter book. Oh, and she has created a series on the new Instagram TV. But she rarely makes her bed. So there’s that.

She recently asked me when she can come to work with me and help out. I told her that I would have to check my schedule to see what might work. She responded with a very simple, but surprisingly profound question:

How do you determine your schedule?

 Good Question

This made me think more deeply about my schedule in an attempt to explain it. I told her that I start with deadlines. I look at all of the things that The Weaponry has to create and the due dates for each. Then I schedule my time to focus on those projects, in order of priority, from hottest to coolest.

flat lay photography of calendar
Your schedule starts as a blank slate. How much time do you put into thinking about how you fill it?   

But this begs the question, ‘If it weren’t for deadlines or due dates, what would your schedule look like?’ For entrepreneurs, there is always something more to do. But this is really true of every job, right? So, how do you add tasks to your schedule that don’t have deadlines?

blur close up depth of field focus
If you haven’t thought deeply about how you schedule your day, maybe you need a 12-year-old daughter.

How I Do It.

I have found there are 3 things that I incorporate into my schedule, despite the fact that they don’t have due dates.

Connecting:  I am a natural connector.  I think people are the most interesting machines on the planet. I highly value my relationships. More importantly, I maintain my relationships. And when I think of someone, or have a little bell that dings in the back of my head that lets me know it has been too long since we’ve last spoken, I reach out. This is an important part of my regular schedule, and should be part of yours too.

Closing Gaps: At The Weaponry we spend time exploring the gaps between where our organization is today, and our idealized, fully formed organization of the future. As a result, we often think about our shortcomings. Although I don’t think of them as shortcomings. I simply see things that we are not doing, or don’t have yet, that we will in our ideal state. This is about improving our processes, procedures, systems and infrastructure. Entrepreneurs call this working on your business. But I think everyone can benefit from more gap closing. Except maybe The Gap.

Things that excite me: I always leave room for things that interest me. Since we are an idea generating machine, there are always exciting ideas bouncing around our office. I try to find as much time to explore those ideas as possible. This could involve a new way to look at our clients’ challenges. It could be a new product idea, an additional service, or an idea that could transform our business. I often get excited about new ideas for t-shirts, buttons, stickers or hats for The Weaponry. I love thinking about new messaging for our walls too. Most businesses could benefit from more time exploring good ideas. I do it everyday. You should pencil in some Idea Time this week.

Key Takeaway

Our lives are full of deadline-driven must do’s. They become the studs around which we build our daily schedules. But the key to making each day great is the elective activities you work into your calendar. Whether you use the same approach I do (time for connecting, closing gaps and ideas that excite) or your own formula, make sure your daily schedule isn’t simply driven by email requests and meetings. As Steven R. Covey notes in his book The 7 Habits of Highly Effective People, engaging in important, non-urgent activities is a key determinant of success. Remember that as you schedule your week.

And Ava, this Friday looks like a good day for you to come to work with me. Make sure your pencils are sharp. (That’s just an old expression. I guess it means, make sure your laptop is fully charged.)

 

Why I embrace last-minute requests and ridiculous deadlines.

Wouldn’t it be nice if everything in life worked according to your schedule?  You simply set the amount of time you need to handle anything, personal or professional. Then nothing ever challenged your pre-established timeline. That would be pleasant. And it would bore me to tears.

The world doesn’t conform to your schedule. Business, and life, are far too unpredictable. As Nationwide Insurance used to say, life comes at you fast. Really fast. Opportunities and threats appear in a blink. In the social era you need to respond before your opportunities become yesterday’s tweets. You must be able to thwart threats before they become Napa-sized wildfires, engulfing your home and vineyard.

Get Creative

But opportunities abound in the imperfect schedule. As the Founder of the Advertising and idea agency, The Weaponry, I am always thrilled by quick deadlines. They add excitement to the work. They test our abilities. They push us to learn what we can do without.

Ridiculous deadlines present favorable conditions for creativity too. When time is short the approval process is also short. You run through fewer approvers, who tend to be more accepting of really great creative solutions. So better ideas are often produced under tight timelines, because the client has less time for second guessing.

Walt Disney’s Magic

Recently I read about a crazy request Walt Disney received from Pepsi in 1963. Pepsi had been working on a collaboration with UNICEF for the World’s Fair, but had failed to come up with a worthwhile idea. So they approached Disney with the daunting task of creating an exhibit to fill their 94,000 square foot exhibit space. But they had far too little time and far too little money for the challenge. So Joe Fowler, the supervisor at Disneyland, turned down their request.

When Walt Disney heard this he was furious. He said, ‘I’ll make those decisions,’ and then informed his team that they would indeed take on the Pepsi project. To solve for the time, space and money challenges, Disney devised a boat ride through a canal, surrounded by animated dolls from around the world. The dolls sang a song that Disney commissioned the Sherman brothers to write. As Disney described the concept of the exhibit to the Shermans, he explained ‘It’s a small world after all.’  That, of course, became the name of the song, and the ride itself.

The World’s Fair exhibit was a resounding success for Pepsi and UNICEF. Today, almost 55 years later, that boat ride is still one of the most popular attractions at Disney World.  And its theme song is known around the world.

Conclusion

Your next great opportunity may show up at your doorstep wearing a really short deadline. But don’t be too quick to shoo it away. Don’t focus on all the reasons you can’t take on the challenge. Focus on the possibilities. That opportunity just may turn into the greatest thing you’ve ever done. But if you truly can’t find a way to make it work, send it my way. I love a short deadline after all.

The one simple thing that separates Dreamers from Doers.

Everyone has a dream. Me. You. MLK Jr., Dorothy from The Wizard of Oz. Yet the number of people who do something to make their dreams a reality is really small. Like Pluto vs. Jupiter.

So what’s the difference between Dreamers and Doers?  I’m glad you asked. Wait, I asked. Well, I’m glad I asked because you should know the answer.

A Deadline.

A goal is a dream with a deadline.  -Napoleon Hill

Time constraints motivate you to action. If you are serious about your dream, give yourself a deadline to make it a reality. Because a deadline tells you what you need to be doing now. (Hint: You can start by setting a deadline to take the first step. I do this a lot.)

When you were in school it was easy to set goals like these:

  • Make the varsity team.
  • Make first chair violin.
  • Get the lead part in the play.
  • Go to a party with cool kids.
  • Become an emcee of the Winter Carnival Talent Show and orchestrate a stunt to get the show shut down forever.

In school you have 4 (or 5) years to bring your dreams to life. That finite amount of time is a critical driver. Because you can’t stay in school forever (unless you were this guy named Brucey from my hometown).

But once you get past your schooling you start to float in an odd, timeless space. It’s like losing the effects of gravity once you leave Earth.  Time is still slipping by. You just don’t notice it until it’s too late. Like alcohol in a really fruity drink.

We all need time to ground us.

Time scarcity is what tells us what we need to do NOW.

If you want to accomplish great things, travel exciting places, learn new skills or start a business, you need deadlines. The deadline creates the urgency to act today.

When I turned 40 I set a goal of starting my own ad agency by the time I was 42. I easily beat the deadline. The time limit forced me to start moving. And when I started moving things developed quickly.  I set timelines for other business plans at the same time. Those plans are coming to life now too. On the other hand, I have a whole mess of dreams that I haven’t given deadlines. Those dreams are just floating out there, like Sandra Bullock, calling to George Clooney.

Dreaming is fun and easy. But it won’t translate to wealth, experience, accomplishment or pride without a deadline. Set one for yourself. Or set a lot of deadlines. Accomplish a lot. I’m giving you until midnight on Sunday to take the first step.  You’re on the clock. Tick…Tick…Tick…