Starting is the Hardest Part

Photo by Jukan Tateisi

I really don’t want to write today. Or do anything, really. I just stepped off a 13-hour flight that took me across 8 time zones. Picture a groggy brown bear after a four-month hibernation and you’ll have a pretty good idea of my current attitude.

I’m better off getting some rest and taking a crack at it tomorrow. 

At least, that’s the story my inner voice desperately wants me to believe. 

Like a second grader trying to get out of doing her chores, my inner voice lays it on thick.  “Hey, I know you have good intentions, but you don’t really need to do that productive / creative / useful thing today. You’re tired. You’re definitely better off working on it tomorrow. Or the next day.” 

That’s what makes starting the hardest part. My brain sees the long, bumpy, and seemingly endless road that lies ahead and does everything within its power to convince me to stay off that scary road. 

Researchers have begun to shine light onto the root cause of this struggle. “Medical imaging studies have shown that mathphobes [people afraid of math], for example, appear to avoid math because even just thinking about it seems to hurt. The pain centers of their brains light up when they contemplate working on math,” explains Barbara Oakley in her book, A Mind For Numbers

Sometimes I recognize the self-protecting, pain-avoidance strategy that my body employs and can muster enough courage to fight back. The battle against procrastination is never-ending and I’m only starting to discover the best ways to conquer the relentless nemesis. 

My current approach? When I have an idea to do something, I do something related to that idea — no matter how small — immediately.  It’s irrelevant how much I objectively accomplish or if I’m still miles away from the finish line. Instead of measuring the outcome, I measure the effort. 

Here’s how it works for me:

  • I have an idea to do something. For example, the thought to write this article on battling procrastination.
  • At the same time, I was feeling tired after a long day of travel. My brain immediately used this sluggishness as an excuse to avoid effort. Thoughts like, “writing is hard and it will take so long to finish,” and “it’s OK, no one will know if I start tomorrow after I’ve had some rest” pop into my head. 
  • At this point in the scuffle, about 90% of us pause, thank their inner voice for bringing up such valid points, and go on our merry way.  
  • But today, I recognized my opponent and their sneaky tactics. To push through the pain, I chose to cast aside my visions of a finished product and started to write. 
  • I didn’t care about the quality of output or making significant progress. I wrote for 20 minutes and then stopped. 

There is emerging rationale for this technique. Circling back to the study of people who felt pain when they thought about working on math problems, results showed “it was the anticipation that was painful. When the mathphobes actually did math, the pain disappeared.”

And like the arithmetic avoiders, by simply starting to write, my pain faded away. It doesn’t matter how much, only that I do something. Twenty words, twenty sentences, or twenty minutes. Just start.   

And a nice side effect? Without consciously trying to finish writing this article, I did.  

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New Manager Series: The Do’s and Don’ts of One-on-One Meetings

Ben Horowitz, general partner at Andreessen Horowitz and author of The Hard Thing About Hard Things, hypothesizes that “generally, people who think one-on-one meetings are a bad idea have been victims of poorly designed ones” (177). 

I couldn’t agree more. 

The one-on-one (1×1) meeting, done correctly, is the most powerful way to continuously develop a team member, solicit feedback, and work through challenging situations. The problem is that these priceless conversations are usually poorly structured, cancelled at the last minute, or simply don’t take place. The only person responsible for solving these problems and creating an environment where fruitful 1×1’s can take place? 

You. The Manager. 

In this second installment of the New Manager Series, we’ll break down the do’s and don’ts of 1×1 meetings. 


Be consistent. For productive conversations to blossom, the 1×1 meeting needs to actually occur — and on a consistent basis. I recommend scheduling a standing 30 minute meeting every 2 weeks with each of your direct reports. I prefer grouping them on a specific day of the week (e.g. Wednesday afternoons) so I can get into the listening and coaching zone.


Don’t cancel the 1×1 — especially at the last minute. It shows a lack of respect for the conversation and is usually taken personally. Don’t be the sorry-I-have-to-cancel-because-something-else-popped-up manager. 


Ask good questions. I highly recommend The Coaching Habit for a simple playbook for unlocking your teams’ potential through straightforward questions. Ben Horowitz also shared his favorite questions to pose during 1×1 meetings:

If we could improve in any way, how would we do it? 

What’s the number-one problem with our organization? Why? 

What’s not fun about working here? 

Who is really kicking ass in the company? 

What don’t you like about the product? 

What’s the biggest opportunity that we’re missing out on? 

What are we not doing that we should be doing? 

Are you happy working here? 

The Hard Thing About Hard Things, Page 179

And my personal favorite, “How can I make your life easier?”


Don’t talk too much. In fact, the employee should be doing most of the talking. “The manager should do 10 percent of the talking and 90 percent of the listening,” explains Horowitz (179). The exact speaking/listening ratio of your 1×1’s will vary but the general idea is simple: when in doubt, just shut up and listen. If you think you’re talking too much, you definitely are. If you’re getting brief and incomplete answers, it’s your job to ask better questions until the root issue is unearthed. 


Follow up on your takeaway items. The desired outcome of open ended questions are to learn more about the person, their goals, their problems, and how the company needs to improve. When done properly, real problems will be uncovered. Some of those problems will require you to take action outside of the 1×1 meeting to help improve the situation. Set a reasonable timeframe for your follow up — and meet that deadline. This goes a long way in building mutual trust and appreciation that will serve as the relationship cornerstone.


Don’t feel like you need to solve every problem. It’s common for first-time managers to leave the 1×1 meeting and run around trying to fix everything. The key is to understand which items require your guidance and which can be solved simply by listening. Said another way: Sometimes people just want to vent to their manager. 

When I’m unclear whether a 1×1 talking point is a true priority or a venting exercise, I like to empower the employee by giving them the opportunity to create a project. Give them time to ponder the issue and the chance to circle back next meeting with potential solutions, a timeline to resolution, and the resources needed to get it done. Their true priorities will be treated with vigor and that’s your signal to become involved.


Give real feedback. Not just the normal, “I think you’re doing a great job Katie”. I’m talking about specific and actionable feedback that drives tangible improvement and growth. Think back over your career and all the feedback you’ve received. The annual reviews, the post-meeting comments, and client debriefs at the bar. Seriously, really think about it.

How much of it was fluff and how much of it helped you grow as a person and professional? In my reflection I can count the actionable feedback I’ve received on a single hand.

As a manager, you have the power to create real change. But it only happens when you make the effort to identify areas for improvement and have the guts to deliver that message. For each person on your team I know there’s at least one hard conversation you’re avoiding. Step into that uncomfortable place and create real growth.


Don’t make it about you. “The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting,” Horowitz observes. “This is the free-form meeting for all the pressing issues, brilliant ideas, and chronic frustrations that do not fit neatly into status reports, email, and other less personal and intimate mechanisms” (177).

Most managers use the 1×1 as a project catch-up or a place to push forward their agenda. Avoid that trap because the tactics will quickly overpower the meeting’s true purpose: to nurture and grow your team.

Whats your experience with 1×1 meetings and how can you improve the next one?

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Defining Success

Let’s play some Jeopardy. Alex, I’ll take “Dubious Definitions” for $400. 

The answer:

Bill Gates, Michael Jordan, Beyonce, and Elon Musk

I start tapping on my buzzer incessantly as Alex finishes his sentence. My name lights up and the floor is mine:

“When you think of successful, who comes to mind?”

In this imaginary game of Jeopardy, that $400 would be mine. 

That’s because the four names from the answer all fit the standard definition of success. It’s typically someone who a) is proficient in a particular activity (e.g. sport, business, art), and b) has garnered recognition for this ability. 

I struggle with this commonly accepted notion. We’re leaving out many deserving people and including others not truly worthy.

Derek Sivers, entrepreneur and author, also challenges this definition. “What if Richard Branson set out to live a quiet life, but like a compulsive gambler, he just can’t stop creating companies? Then that changes everything, and we can’t call him successful anymore.” (source)

Moreover, what if someone attained their success by acting like a total jerk along the way? Shouldn’t that also be factored into the equation?

With these thoughts in mind, I’ve developed a new model for defining success:

A person’s level of achievement, using their personal goals as the measuring stick

The way they did it, using your personal moral compass as the barometer

This feels like a more complete rubric to me. It takes into account Derek Sivers’ point regarding goal attainment and also accounts for how the person behaved. 

Unfortunately, like most models, mine contains a fatal flaw. We never really know a person’s internal goals. That information is highly personal and rarely public knowledge — unless included in a memoir or if you happen to be best friends with the person. 

I’m tempted to crumple this equation into a paper ball and channel my inner Michael Jordan by dunking it into the trash. But maybe it’s not totally worthless. Instead of using it to evaluate success in others, maybe we can use it to evaluate success in the most important and critical person of all — ourselves. 

We beat ourselves up over being “successful” and doing everything perfectly. I think a cause of much of that criticality is due to an unobjective analysis of what we’ve accomplished. Let’s change that by adding some objectivity in how we judge ourselves, with a new formula for personal success:

My level of achievement, compared to my goals

How I did it

Using this model, we can look back over the past year, month, week, or day and ask ourselves: Have I been successful? 

Now that sounds like a question for Final Jeopardy. 

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