How I’m Learning to Embrace Loneliness

My whole life I have managed loneliness. It’s not the kind of severe loneliness or social isolation equated with depression. Mine is a kind of loneliness that goes with being physically alone, either living alone or being single. And for most of my life, I have been one or both of those things. My loneliness feels more like a gentle sadness of longing or being without. 

For years, when the feeling of loneliness would show up, I would yearn for the thing that made that feeling go away. If I was single, I yearned for a partner. If I was home alone, I yearned for the company of another. 

I recently had a conversation with my friend Ric, who is like a guru to those who know him. I asked him if he ever feels lonely. 

“I am never alone,” he replied, “I am always with myself.”

Ric’s perspective on loneliness set me on a new path. Instead of yearning for the thing that will make my loneliness go away, I am, instead, learning to understand what it is and how it fits in—even belongs in my life. 

Here’s what I’ve learned. 

My loneliness is not a bad thing that I have to get rid of. It is now a healthy part of a balanced life for me. One of the things that comes with being alone is total freedom. I’m not just talking about the freedom to go places, though that exists too. I am talking about a more mundane kind of freedom. I can watch anything I want on TV, for example. I can eat anything for dinner, even gross combinations of food on one plate. It’s a freedom to make any decision I want, any time I want. But this incredible freedom has a price, and that price is the feeling of occasional loneliness. And because I so appreciate my freedom, this seems a small price to pay. 

The opposite is also true. I love being in relationships and with friends. I love the feeling of companionship and togetherness. But when I have that, it also has a cost. And that cost is loss of freedom. When we are with others, we have to consider their needs and wants. Sometimes at the sacrifice of our own. That’s the price of companionship.

The best relationships, the best friendships, and indeed the best personal lives are able to find the right balance between freedom and companionship. It’s sometimes an imperfect dance, but it is not about eliminating feelings of sadness or yearning; it is about weighing costs and benefits. 

Being alone or being with someone is no longer a comparison I make. One is no longer more desirable than the other. They are simply different states of being that come with their own costs. And sometimes the cost for the thing we get is worth it. 

Why We Need Each Other

I try, try, try and fail. Only then will I learn and improve the way to do things.

I go, go, go and trip. I stand up, brush off my knees, look back at what I tripped over so I know what to look out for in the future. Now I don’t have to trip over those things again.

I run faster and faster and faster, then miss my turn and have to go back and try again. But now I know what signs to look for to keep me moving in the right direction.

I go alone, alone, alone until I find someone on the same path and we decide to run together. I share all my falls, trips and missed turns so they can benefit from my effort. They tell me about all their falls, trips and missed opportunities so I can learn from their experiences.

Then together, we can run faster, straighter and more confidently to the place we want to go.

Hands-On or Hands-Off: Which Leadership Style Is Better?

I’ve always sworn by my laissez-faire leadership style. I tend to leave people alone and let them do their thing. I’ve debated my style with others who are more prone to micro-managing. They make the argument that they have to be hands-on because when they are hands off things go wrong too often. 

Who’s right?

I used to give people a hard time if they worked on nights and weekends. I wanted to help them maintain work-life balance. But data that was given to me by Watercooler.ai, an AI company that looks for anomalies in the patterns of our workflow, showed me that I was actually doing more harm than good (which you can read here, if you are so inclined).

To better understand how much is the right amount to engage with our people, Watercooler showed me the data again. Unsurprisingly the right amount does vary by industry. But there is a sweet spot for each company. It turns out that engaging too little or too much can both contribute to increased chance of flight risk. 

Here are two examples:

For Company A, a sales-oriented organization, the optimal number of interactions is about 1 to 2 days during the week (including weekends). In Company B, an online training company, the frequency is interactions on 2.5 to 4.3 days during the week.

What’s important is that we need to strike a healthy balance between a hands-off and hands-on approach. Veering too far in either direction, the data shows, results in an increase of flight risk.

This kind of insight is particularly valuable when we move from one company, culture, or industry to another. What worked in our old job, may not work as well in our new job. AI can’t replace human leadership but can help show good leaders what they need to adjust to be the best leaders they can be for the culture in which they work. 

I’ve become so interested in the data that Watercooler analyzes that I became an advisor and investor in their company. The best part is that I get to have regular conversations with the CEO, Eitan Vesely, and his team and they show me what they are learning. Here’s a clip from a recent webinar we did together:

If you find this interesting and would like to hear more, here’s the link to the full webinar.

Where Does Vision Come From?

Only after years of abuse and demand for change did American revolutionaries embrace the idea of starting their own nation. In other words, the vision came second.

The drive to build a business from scratch is the same. The desire to solve a problem or build a better mousetrap comes first. The vision comes later.

So people feel they need to have a vision before they can do their life’s work or “find their passion” will likely die searching. 

Think of it like going to space—the goal may be clear, and the problems to solve may be in front of us, but the view of the planet from space is unknown until the spacecraft gets into orbit. It is that view that creates the vision for something more profound. As almost every astronaut reports when they return to earth—it was the view, a planet of infinite beauty and without borders—that inspired them to become more idealistic and care more about world peace. 

So, put the need to find a vision aside…for now…and find a problem to solve, a suffering to relieve, a person or people to help. And from that passionate drive to do good, the vision will emerge. It is at that point that the vision will serve as a beacon for something even bigger than the original problem we set out to solve.

Is Your Boss a Horrible Person?

A friend was struggling at work and wanted some advice. So we went for a walk.

“My boss is a horrible person,” she started to tell me.

“Oh my god!” I replied. “Does she kick her dog and abuse her children?”

“No,” my friend responded, confused by my question.

“Ah,” I said. “So we don’t know if she’s a horrible person. All we know is she’s a horrible leader.”

We very often confuse someone’s skillset with their character. Indeed, my friend’s boss may be a horrible human being, or perhaps she’s operating from a place of fear or crippling insecurity. Maybe she’s in over her head. Perhaps she had bad role models as she moved through her career. All we can say for sure is that she lacks the skills she needs to be a good leader.

This is an important lesson.

When we confuse someone’s skillset with their character, we will treat them that way. We will act defensively or aggressively to protect ourselves or our interests, which may only inflame the stress, fear, or insecurities someone has. If it’s coping skills they lack, we may be the ones pushing all their buttons and making a bad situation worse.

In contrast, if we can have empathy for the fact that our boss may simply be lost, afraid or clueless, our attitude, words, and actions will change dramatically. How we show up will relieve tension and actually give us more agency in the relationship.

Of course, we hope that our boss will see how we act as inspiration. But we can’t count on that. All we can control is ourselves. In so doing, we build our own skills and actually become the leader we wish he had. After all, as I firmly believe, taking action to become the leader we wish we had is among the most powerful ways we can thrive in a difficult job.

Should You Give Two Weeks Notice When you Quit Your Job?

In a perfect world, decency, kindness, and courtesy will always prevail. But let’s get real.

A lot of people are starting to argue that giving your two weeks is unnecessary. “They wouldn’t offer the same courtesy to me if they didn’t want to employ me anymore—they would simply fire me on the spot and I would be out within an hour.” 

It’s an understandable response. Often, by the time you’ve finally decided to leave your job, you have compounded a lot of negative emotions towards your employer. Those emotions need a release, and what better way than to stick it to your shitty boss than to simply go and leave them in the lurch? 

It’s tempting to leave with bad blood, but it’s not as self-serving as it might immediately feel at that moment. 

You really should give two weeks notice when you quit, but don’t think of it as courtesy to your company. Think of it as a favor to yourself. It’s an opportunity to set yourself up for success in the long run. Put in your two weeks and then use those two weeks to do some of the best work you have ever done. Make it so that when you leave, they realize that it was a tragedy that they ever let you go in the first place.  

And if there’s just too much bitterness? If it’s just too tempting and you give in to all of that resentment towards your soon-to-be-ex job and leave in a blaze of glory? Just remember this:

The world is small. People know other people, and those people talk. And the truth of it is, when they talk about you, anything positive that you did for that company will never be acknowledged. 

And that new job that you really wanted but didn’t get? Did you ever think that maybe, just maybe, it’s because of how you left the last one?

The One Question You Should Always Ask When Being Interviewed For a New Job

“Do you like working here?”

It’s very hard for people to lie about their own feelings. If they take a minute, and finally say something like “….yeah? Yeah. Yeah, I like it here,” they aren’t being truthful to you or, frankly, themselves.

If they answer without thinking, it’s more likely that they are being truthful. “Oh, I love it here.” Read the emotions on their face, listen to how they say it. If they use the word love instead of like, follow up and ask them why. If they are passionate in their reasons and light up as they go on, their account of what it’s like to work there is usually an honest one.

If you interview with multiple people at that organization and ask them that same question, you will quickly discover if it’s just that one worker who is happy or unhappy or if it’s the whole company that feels the same way.

Your interviewer’s answer to the question “do you like working here?” is probably one of the most honest things you will hear in the whole interview. 

Why You Should Celebrate the Things You Hate

I started my entry-level job, had my own salary, and wanted to get my own apartment. I didn’t have the money to get the apartment I wanted, so I lived in the apartment I could afford. That being said, it was a pretty wonderful little 3rd-floor walk-up studio apartment on the Upper East Side of Manhattan. In the bathroom, there was this quite large heating pipe that ran from floor to ceiling between the sink and the toilet, about three or four inches from the wall. It was an eyesore. It was painted white like the walls… as if it would blend in. It didn’t. And in the winter, it got so hot that if anyone accidentally touched it, they would burn themselves. I hated that pipe.

I couldn’t remove it. I couldn’t hide it… so I decided to celebrate it. I painted it red. Then something strange happened—I ended up loving that pipe. Friends would come over, and if they used the bathroom, they would almost always come out and say, “I love that pipe!” 

So often, we have things about ourselves that we hate, that we try to hide. It never works. Most everyone can see the thing we are trying to hide—our social awkwardness, our receding hairlines, our chipped tooth—so why not celebrate it? Own it. Make it stand out.

I now regularly talk about my social awkwardness or the unique qualities that come as a result of my ADHD as assets that I’m proud of. I love that I go to a party and stand by myself with a drink in the middle of the room. I’m the observer. I think my receding hairline makes me look distinguished. And my chipped tooth makes my smile uniquely mine – not to be mistaken for all those people with perfect teeth.

The next time something goes wrong, the next time you wish something didn’t exist—don’t try to hide it, paint it red.

Should You Tell Your Employees Not to Work on Weekends?

I have always prided myself on being the kind of leader that works to help those on my team maintain a work-life balance. I want people on my team to spend quality time with their families in the evenings and not work on weekends. Even when there are those times when we have to work late or on weekends, I try to give some time back. For example, I’ll try to give them a day off during the week to make up for their lost Saturday. And if anyone on my team sends emails at night or on a weekend, I encourage them to stop doing that. 

So you can imagine my surprise when I found out that I was actually doing damage to the morale of some of the best people on my team.

I’ve been advising a startup called Watercooler that uses machine learning to look for anomalies in company workflow to predict the risk of burnout, the risk of quitting, and gaps in training. On one of our calls, they were showing me some of their data and I was shocked by what it seemed to reveal. 

Below you’ll see a graph provided by the team at Watercooler:

In studying this chart, you’ll find that the employees who are most disengaged from work rarely if ever do work in the evenings or on weekends. Employees who are at high risk for burnout do too much work in the evenings or on weekends. But the best, happiest, and most engaged employees actually like to do some work on the occasional evening or weekend. And the reason is simple: they care. They care a lot. And they really like doing the little extra to help themselves, their colleagues, and the company stay on top of things. 

So when I told my best people to stop what they were doing, I was basically telling them to stop caring. 

I learned that, even if well intentioned, I can’t enforce my idea of what work-life balance should look like. If my best people want to do some work in the evening or on a weekend, and it makes them feel good to do so, then instead of telling them to stop, I have to show appreciation for their extra effort. Making someone feel good for the extra work they do does more to boost morale and good will than trying to force people to stop doing any work during their spare time. 

Certified WHY Coach Program Framework

Learn the exact process Simon Sinek uses to help people discover their WHY and guide them to inspire others.

What You’ll Learn

By the end of the program, you’ll be able to:

  • Explain The Golden Circle and its components — WHY, HOWs, and WHATs
  • Guide someone through a WHY Discovery process that leads to a resonant WHY statement and actionable HOWs
  • Help people use their Golden Circle to make better decisions and create positive change in their careers and lives

You’ll also develop essential human skills you can use every day:

  • Building trust
  • Listening to understand
  • Asking better questions
  • Handling emotional conversations with care

How You’ll Learn

The program includes four structured units combining independent learning, live training, and practice:

Day 1 – The Foundation

  • Get to know The Golden Circle 
  • Find out what it means to bring a Golden Circle to life
  • Learn what a WHY Discovery is, how it works, and what the benefits are

Day 2 – The Human Skills

  • Hone the human skills to guide someone through a WHY Discovery:
    • Creating psychological safety
    • Asking effective questions
    • Engaging in active listening

Day 3 – The Process in Practice

  • Learn notetaking strategies that will help you facilitate a WHY Discovery session
  • Develop the analytic and collaborative skills you need to help someone identify and articulate their WHY and HOWs

Day 4 – The Golden Circle in Action

  • Apply everything you’ve learned to facilitate a full WHY Discovery
  • Learn how to wrap up a session
  • Prepare for your next steps to becoming a Certified WHY Coach

Program Details

Format: 4 live classes + independent learning + group practice

Duration: ~ 8-10  hours per unit (including independent learning and live classes) plus ~5 hours to complete the final exam

Certification Requirements:

  • Complete independent work
  • Attend and participate in all live sessions 
  • Pass a final exam and performance assessment

Your Support Team

  • Regular updates and reminders
  • Opportunities to ask questions
  • Personalized feedback from master trainers
  • Ongoing support through your final evaluation

Program and Participation Terms and Conditions

Our mission is to create a supportive learning environment where we grow together to help others. By joining, you agree to show up in service to one another.

Professional Expectations

  • Attend and participate in ALL live classes in their entirety.
  • Complete ALL assigned online coursework.
  • Must be fluent in English.
  • Show up to live classes, community spaces, and group work with respect, kindness, and gratitude.
  • Support your fellow participants with a service mindset.
  • Keep all personal stories shared during the WHY Discovery process confidential.
  • Approach the WHY Discovery journey with empathy, integrity, and care for those you serve.

Participant Cancellation and Transfer Policy

  • Cancel up to 10 days before your cohort start date: Full refund.
  • Cancel less than 10 days before: We’re unable to offer a refund at this stage.
  • Transfer up to 7 days before: You may transfer your spot to another participant for a $200 (USD) fee.

Recording and Photography

  • Participants may not record or screenshot sessions.
  • The Company will record sessions and make them available internally for 30 days.
  • By joining, you understand you may appear on screen and agree that recordings and photos may be used by the Company for program or marketing purposes.

If you prefer not to be included, please contact the team before the first session at [email protected].

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The Art of Creating Fiercely Loyal Customers

Quantity: 1 quantity = 1 team of up to 20 participants

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For teams of 20+ contact us

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Purchase: $999

The Art of Creating Fiercely Loyal Customers

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Curiosity is essential
                for progress.
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A spark is something quite small and, by itself, not very powerful. But a spark has the ability to ignite. An idea is like a spark; alone it is just a set of words, but it too can ignite. A great idea can inspire others to dream bigger. Let us all work together to ignite something greater than ourselves.

Let us all be a Spark of Optimism.