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The Power of Asking Better Questions, The Dangers of Trying to Make Your Family Proud, & Why Respect is More Important Than Approval (Office Hours)

I have two episodes of Office Hours that I’m excited to share with you this week:

In the first, Isaac and I talk about the power of daily challenges and we answer the following four listener questions:

  • How do I get a job after a failed startup?
  • How do you answer a question about weaknesses in a job interview?
  • I’ve been at my current job for three years and my boss has never brought up the topic of giving me a raise, is this a bad sign?
  • I have so many things to do that I often feel overwhelmed and don’t get started on anything. How do I start working towards my goals?

In this episode, we cover topics like non-zero days, daily challenges vs. big end goals, going from a startup failure to finding a job, what are employers are looking for when they ask applicants about interviews, how to ask for a raise, taking responsibility for assessing your own worth in a job, getting overwhelmed by wanting to do too many things, and much more.

In addition to listening on on iTunes, YouTube, direct download and all major podcast platforms, you can get started simply by clicking “play” on the below video:

In the second episode, Isaac and I riff on a recent blog post by Isaac about the idea of work-life balance and then answer the following questions:

  • How do I find my passion and make my family proud?
  • How do you ask more relevant questions and take action according to the answers?
  • How do you tell your family an important truth that you know will disappoint them?

In this episode, we cover topics like the guilt lurking behind work-life-balance questions, what it means to do good for your family, the danger of trying to make your family proud, taking responsibility for your professional development, asking for critical feedback, why parents are invested in their kid’s decisions, why respect is more important than approval, and how to be clear about what you want going into a hard conversation.

You can check out this episode below:

Don’t hesitate to leave a comment letting us know what you think. And if you have a question you’d like to hear us address, leave a comment on YouTube or send me a tweet.

I hope you enjoy and I look forward to hearing from you.

Create a great day,

T.K. Coleman

Why I Listen to Christmas Music Every Day

Photo by Rodion Kutsaev on Unsplash

My favorite uncle’s name was Cleatus. We called him “Uncle Cleat” for short.

In many ways, he was like my Santa Claus. He was always jolly, somewhat chubby, and never failing in his ability to make you feel like you were the most important person in the room. My parents never taught me to believe in Santa, but with people like him in my life, I never lacked a sense of Christmas magic.

Uncle Cleat owned a furniture store on a busy intersection of the south side of Chicago. It was called Custom Corner. Every year during the holiday season, he would decorate the store with holiday ornaments and Christmas lights to prepare for the big revenue generator of the year: selling Christmas trees to all the families on the south side.

My father would take my brothers and I to the furniture store to help out. I don’t ever remember doing any actual work. I was the baby of the family and was allowed to wander around and hang out while my older brothers and cousins helped customers carry their trees to their cars. I remember how huge the store seemed to me. I would get lost looking at all the bright lights and cool trees of different colors. At times, I felt like I was an actual visitor to the North Pole. There was even a huge stock room in the back where the workers would take breaks and clown around. I often fancied that this was what it must have been like to hang out with Santa’s Elves.

And then there was the radiant presence of Uncle Cleat. Everyone loved him and his smile lit up a room as wonderfully as any Christmas tree. “What’s up Teeek-Man” he’d yell at me whenever I walked into the room. He always had a silver dollar or a new toy to give me whenever I saw him too.  One of the best things about Uncle Cleat was that he looked exactly like my dad, but he was much more of a goofball. So it was kinda like having a serious dad and a silly dad all at the same time. I honestly can’t think about him without smiling or laughing. Not even possible.

As life is bound to do for all of us someday, it abruptly ended for Uncle Cleat. I wasn’t a kid anymore when he died, but there was nothing about being in my early twenties that made it an easy loss to handle. Uncle Cleat was my man. Whenever I felt self-doubt, he would say “Lift your head up, man. You’re a Coleman.” And his confidence would transfer to my spirit like magic. Whenever I got into a stupid argument with my parents about something, Uncle Cleat was the guy that would have my back. He would talk my parents into taking it easy on me and he would talk me into taking it easy period. When I would come to him seeking guidance on life, he would remind me of how important it was to live with conviction and let go of my paranoia about making the wrong decision. He was an acnhor for me in more ways than I describe.

I didn’t always listen to Christmas music every day. Like most people, I enjoyed holiday songs during the holiday season and I rarely thought it about besides then. This is how life was until about the age of 21. Then one day, there was a Christmas in July special on television and I felt the spirit of my Uncle in the music. I could sense his silliness, his optimism, and his unflinching confidence flow into me through the music. And every single time I’ve listened to Christmas music since then, the experience has been the same. Whether in April or August, I can feel the aliveness of all the magic and motivation that my Uncle Cleat represented for me when I listen to Christmas music. And that’s why I listen to it every day. It’s not only how I keep my uncle alive, but it’s also how I keep a very important part of myself alive. It’s a way of connecting to an energy that I hope to embody for my nieces, nephews, and everyone else that might look to me for inspiration some day.

My hope is that when life comes for me as it once came for him, someone somewhere will keep the tradition of magic and motivation alive by firing up a little Nat King Cole or Bing Crosby in the middle of those April showers. And maybe this will inspire a few more people to believe that you don’t need to wait on a holiday in order to experience its cheer. Sure, people may laugh at you as they have laughed at me, but as long as they’re laughing, the spirit of Christmas will never die.

Take a Walk on the Dark Side

Photo by Artem Kovalev on Unsplash

“One man’s garbage is another man’s treasure.” Remember that one?

Here’s an often overlooked application of that idea: it also applies to your concept of being positive.

We all get the idea that one person might love video games while another person hates them. We all get the idea that one person might love visiting museums while another person finds it to be a drag. We all get the idea that one person might love having lots of alone time while another person sees that as a nightmare. When it comes to hobbies, entertainment, and recreation, we all understand the idea that different people are turned off and on by different things. But when it comes to our ideas about what it means to be a positive person, we tend to act as if there’s only one right way to think.

Case in point: Back in my college days I worked with a guy who was always perceived as a “negative nelly.” The reason was because he always focused on bad news whenever anyone asked him what was going on. And the funny part about it was that he would reach as far as he needed to reach in order to have some bad news to share. That is, if nothing was going wrong in his life, he’d make it a point to find something negative to report about someone else’s life even if he didn’t know them. Bill focused on other people’s problems with same degree of intensity as he focused on his own.

For instance, if you were to say “Hey Bill, what’s going on?” He’d look around and lower his tone as if he were getting ready to tell a grave secret. Then he’d say something like “Do you know John, the guy that works in the kitchen? Well, he has a friend named Sandy whose cousin is having a real hard time right now. Apparently Sandy’s cousin has a best friend who was supposed to be in the olympics or something like that and he got injured some kind of way and the whole family is just a mess because of how hard he’s taking it.”

Bill’s stories were always so tough for people to listen to because they required you to feel bad and say things like “I’m so sorry to hear that” unless you were okay with seeming like you were a total jerk who lacked empathy for others. It didn’t matter what day, time, or occasion it was. If you asked Bill about anything, he’d give you a story about something bad that happened to someone somewhere and you’d end up feeling a little less happy about the fate of your fellowman. Sometimes I would fantasize that Bill was a kind of superhero whose sole purpose was to remind people of the Yin/Yang principle.

The funniest thing about working with Bill, though, was all the fruitless effort everyone would pour into trying to make him more positive. People would always tell him to cheer up or they would try to direct the conversation towards something positive. Some people would awkwardly say things like “Hey Bill, did you do any FUN & EXCITING things this weekend?” That never worked though. Bill would just say something like “No, it was way too crazy for any of that. I had to talk to my girlfriend Sheri for like 5 hours because her son has just been driving her up the wall this week.” If you tried to beat Bill in an energy battle, you would lose every single time.

I don’t think people really cared all that much about Bill’s happiness. I think they were just trying to protect themselves from having to listen to his stories because it negatively affected *their* happiness. What I realized about Bill was that he actually enjoyed *sharing* bad news. For Bill, that’s the kind of stuff that was most worth talking about. Based on his value system, it gave him a sense of belonging and purpose to play the role of the guy who was always aware of bad things and always there for the people who were going through them.

One of the reasons Bill always had so many bad stories to report was because he was always spending his time listening to people talk about their problems. And if no one was around to talk about their problems, Bill would go search them out. I wouldn’t say that Bill was particularly “happy” in some stereotypical sense, but I would definitely say that he found great meaning in the practice of focusing on other people’s unhappiness. When people would try to make him become more positive, I would just think to myself “What he’s talking about may be garbage to you, but it’s treasure to him.”

I love horror movies. Not the blood and gore kind, but the suspenseful thriller kind. Movies like The Shining, Rosemary’s Baby, Get Out, Mama, The Witch, Sinister, etc bring me to the edge of my seat and they inspire me to think deeply about the nature of the universe, the possibility of the supernatural, the problem of evil, and how we can improve our ability to deal with the shadows in our own lives.

My wife, however, hates horror movies. And it’s not just a matter of aesthetic taste either. If she watches the kinds of horror movies I like, it ruins her sleep and it will freak her out for at least a few days. The experience of watching horror movies, for her, is a form of negative thinking. To watch a movie like Sinister would be the equivalent of making her imagination a breeding ground for fear. But here’s the funny thing: she loves to listen to me talk about horror movies after I watch them. She likes it when I tell her stories and philosophize about them. But she credits this to my personality, not to any messages or insights that are actually in the movie.

Like Bill, I find great meaning by paying attention to things that others might find depressing or frightening. That doesn’t make me negative. It makes me negative to be around when you’re the kind of person who seeks meaning in different types of things.

I once read in a self-help book somewhere the following advice: “Never try to force another person to be positive.”

I think that’s good advice, but we should take it one step further: Never assume that your definition of being positive is the same as the other person’s. The kinds of thoughts that you treasure might be boring or bad to someone else.

In your quest to make the world a more positive place, be open to the possibility that the people you’re trying to inspire are already enjoying themselves far more than you think.

When You Talk About How Easy Your Work Is, You Invite More Scrutiny

Photo by rawpixel.com on Unsplash

In When You Deliver Work Late, You Invite More Scrutiny, Isaac Morehouse argues:

Here’s another reason to get your work done fast (yep, even (especially!) deep, creative work):  you’ll get less scrutiny and fewer requested edits…Every day past expectation the project takes, the expectation for perfection ratchets up.

From your customer’s perspective, it goes something like this: “I’m waiting so damn long for this thing, it’d better be perfect.  Is it perfect?  I don’t know.  Maybe we should tweak this one more thing…”

Creative types are notorious for delivering later than the expectations they set.  Then they get frustrated when people want to make changes and get picky.  When you kill momentum, you turn an otherwise big, excited greenlighter into a slow, skeptical analyst.

The idea is simple: When you wait for longer periods of time to show your work, you raise the bar of performance. Time is an investment just like money. When people spend more money on your work, they expect more from you. Ditto for time. If I have to wait 5 minutes for something, waiting is just a part of life. If I have to wait 5 weeks for something, it needs to be awesome.

If you want to avoid unnecessarily high scrutiny, work fast and update frequently when you can’t.

Here’s another way to avoid unnecessarily high scrutiny: Don’t make the slightest mention of how easy you think a project is until you’ve finished it and completely nailed it.

Whenever you say something like “this is too easy” or “that will be a piece of cake”, you’ve just made it much harder for your audience to be impressed with your work. When it’s time to evaluate your work, people will think “If this was really easy for him to do, then this is going to be really impressive.”

If you’re just on time, it will seem late for someone who thought it was easy. If it’s just above average, it will seem below average for someone who thought it was easy. If you show signs of struggle along the way, it will look arrogant, or naive, or dishonest for someone who said it would be easy.

If you’re hanging out with friends and talking about a subject that no one is going to call your bluff on, then saying things like “Oh that’s easy” is impressive and it makes you look cool. If you want to see proof of this, tell your friends that you love math and most of them will instantly respect you for being good at something they fear. None of them will hand you a piece of paper with equations to solve. The rewards for bragging about your abilities or downplaying the demands of a task are easy to obtain in a casual social setting.

In the professional world, the rules are the exact opposite. The moment you say something is easy, you just raised the bar of performance and you’ve established the expectation that your work will be done early and with excellence. You’ll be given more responsibilities and you’ll be greeted with less forgiving standards. And when you fail to produce remarkable work, people will feel confused or concerned.

Here’s a little anecdote a friend shared with me to illustrate this point:

I’ve made this mistake. I was asked about a project and responded with “Oh yeah, that’s easy, can definitely get it done soon.”

He looked at me said, “If it’s so easy then why isn’t it already done?”

Lesson learned.

There’s a series of videos you can find on YouTube called “Never Celebrate Too Early.” These videos show highlights from games where one team was clearly in the winning position and it seemed as if victory were certain. Rather than staying focused, finishing the job, and celebrating after the contest was definitively over, the winning team celebrated early (and arrogantly). And in a stunning turn of events, a miracle happens for the team who looked like they were going to lose. What initially seemed to be an impressive display of confidence was revealed to be an immature lack of respect for what it takes to finish the job.

Here’s one of my favorites of a soccer goalie who celebrates too soon after making an impressive block:

in every one of the examples in this video, the losing team was actually good enough to get the job done. Their only problem was that they thought it was too easy.

If you’re looking for an alternative way to sound sure of yourself, a simple “I got it” or “I’ll have something to you by {insert date here}” should do the trick. Be confident in your work, but if you want to overdeliver, don’t make the mistake of overpromising.

Focus on your work and finish the job. If it’s really too easy for you, let your final results do the talking.

Use Your Free Time to Create More Freedom

I constantly hear people say “I don’t want to talk or think about work when I’m not at the job.” These are usually the same people who are so worn out by work that they define “relaxation” primarily in terms of being off the clock.

Free time is great, but the whole purpose of free time is to actually enjoy, experience, and enhance your freedom.  If you’re spending your free time worrying about work, complaining about work, resenting work, or getting anxious about the next time you have to go to work, then your free time isn’t very free. Since your free time isn’t free anyway and since you’re thinking about work anyway, you might as well just use your free time to consciously improve your work life.

If you hate your work life, then the last thing you should do is try to escape from it. Instead, work even harder at creating patterns of efficiency and effectiveness that will allow you to transform your work days into something you truly look forward to.

In Getting Things Done, David Allen wrote “Your best ideas about work are most likely to come when you’re not at work.” When that happens, will you be available to those ideas or will you be too busy trying to tune out every thought related to your job? Hard work is hard, but it only gets harder until you put in the work necessary to make it more feasible and fun.

Instead of using your weekends to escape your weekdays, use your free time to develop habits and skills that will provide you with greater mastery, freedom, and enjoyment throughout the week. Instead of seeing your free time as a fleeting reward you get for putting up with a job you hate, see it as an opportunity to gradually create an everyday lifestyle that you can celebrate or at least tolerate.

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