The spring of 2015 was one of the most exciting albeit challenging periods of Alexa von Tobel’s life. Just off a $35 million financing round for LearnVest, a company she had launched exactly five years earlier to help American families with financial planning, Alexa was fielding multiple acquisition offers. She was at a critical juncture in the company’s growth and has just finished overhauling her management team. She was also expecting her first baby any day. On top of it all, Alexa was still on the line to manage her team and continue her role as a very public face for the company and, increasingly, for the financial industry.

“In a weird way, the level of craziness provided an even greater sense of perspective and judgment,” Alexa explained to me. “I kind of felt like I was doing an Ironman—you can’t get too stressed about a few miles of swimming or the hundred miles of biking, because you’ve got a marathon waiting for you after that. The fact that such extreme things were happen­ing at the same time conjured up a forced sense of perspective and calm, reminding me what really matters and preventing me from getting too consumed by any one of the challenges I was facing. If bad decisions are made when we lose perspective, then facing all of these important moments in my life—all at once—was a good thing. Paradoxically, the busier you are at any moment in time, the better your decisions may be because of the greater perspective you have. Bringing life into this world, unsurprisingly, brings per­spective.”

The many challenges Alexa faced kept her from becoming overwhelmed by any one of them. Alexa was able to compartmentalize and focus on each with an eye toward the fu­ture. In her decision to sell her business, she focused on the three constituencies she served—shareholders, employees, and clients—and led a process that proved successful for everyone involved. Alexa sold her company, LearnVest, to Northwestern Mutual on a Wednesday for a reported $350 million and then went into labor on Sunday.

Alexa kept a longer perspective and managed each challenge on its own. When viewed in context of her ultimate goals—becoming a mother, leading her team, and ensur­ing a good outcome for her company—the day‑to‑day issues were dwarfed.

As you encounter such periods in your own career, compartmentalize each drama indi­vidually and remind yourself on the horrible days that tomorrow will be better. Compartmen­talizing doesn’t mean burying or denying the emotional toll: it means facing one challenge at a time and using each one to provide more perspective for dealing with the others. Storms have the habit of feeling like their own little worlds, even though they’re just weather patterns and they move on.

Compartmentalizing is just as hard on a daily basis as it is during a perfect storm. The more responsibility you bear, the more your collective concerns will limit your productivity. To move forward, unbounded by the anxieties and insecurities of the moment, you must apply controls to the energy you spend assuring yourself that all is OK.


Over the years, I have come to recognize the amount of time I spend checking things: Daily sales data, website traffic trends, what people are saying on Twitter, analytics for our customers, team progress on projects, the list goes on. For you, it might be diving into a spreadsheet to manipulate budget numbers or scanning through your unanswered emails again and again. When you’re anxious about your business, there is no easier quick-relief antidote than checking things. The problem is that you could spend all day checking things and fail to do anything to change things.

I call it insecurity work—stuff that you do that has

1. no intended outcome,

2. does not move the ball forward in any way, and

3. is quick enough that you can do it unconsciously multiple times a day.

Insecurity work puts you at ease, but it doesn’t actually get anything done.

The antidote is a combination of awareness, self-discipline, and delegation. Whether it is googling the same search terms again and again or constantly checking your in‑box as if it were a boiling pot of water, you need to identify these behaviors to then change them. When you spend thirty minutes going down a rabbit hole to answer a particular question, be sure to ask yourself, “Why is this question important and how is the answer actionable?” If theanswer is just self-assuring but not actionable, it is likely insecurity work.

Once you’ve identified your insecurity work, establish some guidelines and rituals for yourself. For example, you could allow yourself a period at the end of every day, say thirty minutes, where you let yourself go through the list of things you’re curious about. Put all of your mosquito bites in one place and allow yourself the pleasure of scratching them all at once.

The purpose of reducing the hours you spend on insecurity work is to free up your mind, energy, and time for generating and taking action on new ideas instead of checking in on old ones.


Whether managing one of the most difficult periods of your life or just the everyday ups and downs, you can make progress only by focusing forward and removing yourself from the constant concern for what has already happened.

During one of my recent trips to Japan, I spent some time at a Buddhist temple learning about rock gardens and the design practices behind them. In these gardens, small, finely washed rocks are immaculately raked into lines and curves that create remarkable designs around larger boulders that serve as the rock garden’s anchors. One Zen principle lay in the process of raking lines in the rock garden. If you focus on each line as you make it, it isn’t straight. Instead, you must focus ahead to keep the line straight as you rake.

I was struck by how this Zen principle relates to leading a team through daily chal­lenges while staying true to a long-term vision. If we rake with heads down, always con­cerned about the lines of stones beneath our feet, our lines run amok. The insecurity work we do every day is the equivalent of leading a journey focused only on what is immediately concerning us—beneath our feet—rather than focusing on where we want to be. But if you compartmentalize your ideas and look ahead, and worry less about day‑to‑day concerns, you’ll eventually look behind yourself to see the line you drew was much straighter. You will arrive much closer to your vision.

From THE MESSY MIDDLE by Scott Belsky, published by Portfolio, an imprint of Penguin Publishing Group, a division of Penguin Random House, LLC. Copyright © 2018 by Scott Bels