Remote working Q&A, tips and tools for first-timers and old pros

If you have questions, I can help. I’ve been running a company remotely for almost a dozen years. Based on completely unscientific research, (diligently observing both Facebook and Instagram), here are the top three questions people want answered, along with three bonus tips.

1. Do I have to wear pants?

The first question you may have is, what qualifies as pants? Sweatpants? Yoga pants? Pajama pants?  The answer is, it doesn’t matter. What’s in your mindset is more important than what’s on your body. If wearing sweatpants, yoga pants or pajama pants puts you in a productive state of mind, go for it. If it makes you sleepy, put on something with a belt.

2. What about my kids?

Depends on the situation. If a video meeting isn’t going well, bring ‘em in and let the cuteness work its magic. A little levity can’t hurt. If showing that you’re a fun-loving, accepting parent, maybe the folks on the other end of the call will have empathy for you. You could even give your kids lines to rehearse, like “Dada/Mama, come play!”

3. What about my dog?

One word: bones. If you’ve got a big dog, get a big bone. People who love dogs will love seeing your dog, and hearing said dog, for a bit. But the more a dog disrupts a call, the more it can devolve from sweet and funny to annoying and unproductive. My dog’s the sweetest dog in the world, but only for so long. You can also give poochy some outside time. Dogs need exercise. Zoom calls are good excuses to get them more.

Tip #1: Snooze

As you’ve already realized, self-care is crucial, starting with sleep. You may have heard about or read the book Why Sleep Matters. I don’t want to be all TLDR-y but I can sum it up pretty briefly: Sleep is good for you. It’s good for your brain, body, and life. It helps you be more productive and just plain happier. So a), hit the snooze button in the morning. Hit it twice if you want, get a few extra minutes of sleep, you don’t have to commute anywhere except downstairs. And b), nap. The great thing about working remotely is you can schedule “meetings” that are actually little breaks where you close your eyes. Just don’t abuse the privilege, and don’t rampage through the pantry when you wake up, like I sometimes do (and regret within minutes).

Tip #2: Move your body

Do workplace yoga, walk your dog, turn your unmoving stairs into a Stairmaster. Watch fitness videos. Companies like Blink Fitness and Orange Theory are offering them for free during these challenging weeks. Activate your body and it will activate your mind.

Tip #3: Make dates

Even though you can’t meet in person with trusted advisors and confidantes, you can still get together with them online. I’ve spent more time on Zoom in the past week than I did in the past year, catching up and working with friends, mentors, and coaching clients. If NASCAR can run a virtual race, you can have virtual coffees.

Super bonus tip:

There’s an incredibly productive, efficient and useful tool called a Language Audit that’s perfect for a company to do while they’re working remotely. Click here if you want to Zoom about it, pants optional.

News Flash: Mr. Rogers was a badass

The fearless badass himself.

I saw eight movies over the holiday break and the most memorable one may have had the most boring subject matter: a quiet little man in a cardigan and sneakers.

A Beautiful Day in the Neighborhood is about a writer named Lloyd Vogel, who in 1998 was assigned a 400-word piece on Fred Rogers--Mr. Rogers, to the world--for a feature in Esquire magazine. Lloyd was a cynical guy, damaged from his past, and he approached the job like all of his other assignments: with great skepticism, like a dog sizing up another dog, sniffing him out and even barking at him a little. Challenging him.

Mr. Rogers didn’t take the bait. He opened himself up to Lloyd with open arms, and helped him change his life.

There are so many wonderful lessons from the movie. Compassion, unconditional love,  openness, receptivity, a blissfully open-eyed childlike approach to the world. But what stood out most to me about Fred Rogers was his fearlessness.

He wasn’t afraid to love someone who other people had a hard time loving, or show compassion for somebody who was struggling. He was fearless in every little every day situation. The ones that happen often and accrue in your psyche, good and bad.

For example, I was recently walking my dog Nola and when we passed another dog, the two dogs started growling at each other in a really menacing way. The woman with the other dog said, “Well your dog isn’t very nice.” And I snapped back at her, “Well your dog isn’t very nice either!” and Nola and I stomped away (well, Nola just walked normally).

As I stomped I also regretted. I didn’t like what I’d said or how I said it and I wondered what it might feel like to be unafraid of criticism. To be kind when faced with the daily situations that challenge and even scare us that Fred Rogers jumped into cardigan-first.

Spending time with someone who’s sick or dying, embracing people who don’t fit in, being quick to love instead of being quick to judge. Being the bigger person when plans go sideways and when blame is to be had. Those situations take fearlessness and Mr. Rogers was the master practitioner. And teacher.

One of my favorite parts of the movie is when Mr. Rogers deflects any notion of saintliness or perfection. He admits his struggles raising his two sons, the challenges they had, and how they worked through them. It made me like him so much more. There’s fearlessness in acknowledging the foolishness of chasing perfection. I’ve broken my biggest New Year’s resolution already and it’s not even the new year yet!   

Fred Rogers was so clear on his story. He loved humans because he appreciated imperfection, in himself and in everybody else.

As the new year gets going, take time to fearlessly embrace your imperfections and see how it helps you tell your story. It’ll help bring more of you to the world, shine a light on who you are, and what you have to offer. See other people and be seen.

And if someone barks at you, be fearless enough to try to understand their story instead of assuming they’re just a bad dog. You might help them make their life better, and in turn, they might do the same for you.

Remember, it’s not “Shop Ye Merry Gentlemen.”

As you feverishly peruse the Black Friday offerings and hover your chosen finger over the “buy” button, remember that the best gift you can give yourself this holiday season is time to pause.

Look back at the past year at work and in life and try to take time to think about what rocked, what sucked, how you could have expanded the big happy moments and avoided the big nasty ones. 

Think about how you’ll make more money next year.

Yes, think about how you can get more business. And how you can be smarter, better, quicker, eat less white sugar, and get more sleep.

And then move on.

Money has been proven to improve the way you evaluate your life. But it hasn’t been proven to improve your emotional well-being. Just ask Daniel Kahneman, one of the sharpest tacks in our universal mental toolbox.

So pause.

Pausing leads to emotional well-being, which leads to all kinds of well-being, including the money kind. It’s truly the gift that keeps on giving.

Yes, there are other things your brain needs to think about this time of year. Decorating, shopping, cooking, writing cards, buying that balaclava you’ve had your eye on for sub-zero dog walking. It’s the time of year when, if there’s a window of time, we crash through it and use every minute. Just writing about it makes me tired. 

So here’s a suggestion: Stop filling gaps and start taking pauses. Take time to think. To breathe. To Be Present.

To Be.

Directly or indirectly, the money will come. It will. Soon enough, you’ll work your ass off for it. For now, step away from it.

If nothing else, it’ll give you a little extra time to make room for a second helping of sweet potato casserole. And maybe even a great deal on Black Friday.

In a service business, should you give away anything for free?

Yes please. I’ll take a pallet.

In businesses where you’re selling your brainpower and expertise, and the output that results can be subjective, should you ever work for free?

a)   Of course not, never!

b)   Absolutely, it’s a necessity for my business

c)   Depends on the situation

d)   All of the above

I’m in the d) camp. I like the flexibility of that answer because it’s never an easy question. 

Some may think it’s easy: Don’t do it. Ever ever ever.

But everybody does it.

Entrepreneurs have to do it more than they like, whether they’re newbies on their own or veterans who’ve been in business for decades. 

People in the corporate world do it too, buying potential clients lunch or drinks and dispensing free (and valuable!) advice to woo or impress. They “audition” by doing work or projects on a small scale to show a potential client what they can do.   

They may deny it, but even the most adamant “a) Of course not, never!” people have worked for free.

So how do you know when to say Yes to giving away your brilliance?

In my previous business, advertising, potential clients have a good familiarity of how the business works, so agencies have been giving away work for decades in order to win clients over. BAD MODEL. They put themselves through long, painful, drawn-out pitches where they give away almost unlimited amounts of free work in the hopes of winning some business. Clients pick a winner based on the work presented to them, and allegedly, the best work wins. Except for the times when the client is friends with the agency President, which is often. Did I mention it’s a bad model? 

In my current business, Professional Coaching, where people aren’t clear about how the service actually works, giving away your brilliance can be brilliant. Most people have heard of Professional Coaching but aren’t sure about how it actually works and what you get out of it.

I love offering a free sample coaching session to anyone who’s interested. It’s easy to talk to potential clients about the logistical aspects of a coaching experience--cost, timing, cadence, etc.—until I’m blue in the face. But when I give them the experience, let them live it, coach their socks off and actually show them what it can feel like, light bulbs go off, pulses race, and I can feel their excitement and engagement. For those folks, sampling—giving a taste—is hugely effective, because I’m giving them a great experience.  

Costco has this figured out. Just a little yummy sample can do the trick.

The biggest knee-jerk negative reaction to giving away your product or service is that you’re devaluing your expertise. And while that may seem true on the surface, if you give something away to get someone to understand the value and give them the experience of how great it can be, then it’s the greatest sales tool in the world. 

What can you offer that will help people feel what it’s like to work with you and benefit from your talents, without giving away the store? What piece, glimpse, sneak preview, yummy little taste would be best? Think about it, offer it up, flash your brilliance, and get hired.

This summer, take a vacation, not a workcation

Don’t let this happen to you

As summer winds down and we try to make the most of it, here are 10 things to not do on your summer vacation.

1.   Check your email while you’re building a sand castle

2.   Check your email while you’re looking at a painting at a museum

3.   Check your email while you’re flipping a burger or burger substitute

4.   Check your email while you’re looking at something cool out your window

5.   Check your email while you’re eating or drinking. Especially while you’re drinking.

6.   Check your email while you’re tubing, waterskiing, blueberry picking, bike riding, trail hiking, lake swimming, park picnicking, or pretty much anywhere you’re under a glorious summer sky

7.   Check your email while you’re watching a movie or binge watching a series

8.   Check your email while you’re meeting someone for the first time

9.   Check your email while you’re meeting someone for the 4,197th time

10. Check your email when you’re soooooo tempted to check your email but know that it’s going to lead to somewhere between 12 and 162 minutes of undesired potentially painful extra work

If you want make sure the world isn’t going off the rails while you’re gone, which it most likely won’t because you’ve prepared for it not to, check your email a couple of times a day, maybe when you wake up and before dinner so it doesn’t get in the way of vacation stuff. If it gives you piece of mind and helps avoid the pain of an overflowing inbox when you get back, or if you just can’t stand the idea of not checking at all, just do it.

If you don’t need it at all and can go email-free while you’re away, that’s pretty damn awesome.. If you want to do it and could use some motivation, read this book before you go on vacation.

This summer vacation, try not working, not networking. Instagram the hell out of your doings, just don’t get tempted to look at email while you’re doing it. The best vacations are the ones that don't become workcations!

What being stuck in the NYC blackout taught me about happiness

I was mid-bite, mouth wide open, trying to make my way through a slice of New York pizza the size of home plate, when the pizza joint went dark.

“Hmmm, they’ll just flip the circuit breaker,” I thought, and kept eating. Nobody paid it that much attention. It was New York, after all.

I had a ticket to a great show that I’d bought very last minute so I finished my slice in the dark and headed down 45th Street to the Theatre District, where I waited for the doors to open. And waited. And waited, alongside families from Canada and Long Island and across the world who paid top dollar for their tickets and may have bought them months ago for a big Saturday night out.

As the doors continued to stay closed past the 8:00 curtain time, the sidewalks and streets around the theaters filled up and something started feeling very different. The traffic lights were out, and cars snaked through the streets. Police and fire engine sirens wailed non-stop. The mass of people outside the theaters continued to build.

Waiting for the doors to open (they didn’t)

Finally, a murmur went through the crowd: All shows cancelled. People moved away from the theaters and down the street, heads down. It was as quiet as a jam packed Times Square will ever get.

I was staying in an apartment about a mile away and the sky was darkening, so as the novelty of taking pictures and videos of a mostly dark West Side wore out, I headed back to the apartment and sweated my way up 23 flours so I could be inside before it got pitch black outside.

The apartment was eerily silent and devoid of energy. No fluorescent lights on microwaves or cable boxes, no LED displays on alarm clocks, no refrigerator hum, certainly no TV to turn on or music to play. I couldn’t open Spotify because I only had half a battery left on my phone and had no idea how long the power would be out. I texted my wife every once in a while to let her know I was alive but otherwise shut down my devices.

It got darker. And quieter. A quiet you could hear. More quiet than I’d heard in a long time.

It made me think of a question John Amaechi has asked. John was the first former NBA player to come out as gay, and an amazing speaker and thought leader. My sister has seen him speak and told me about one memorable speech, when he was talking about being a young man in distress over identity and relationships. The question:

What do you see when you’re alone in the dark?

Think about it. What does it feel like to be in a place of complete stillness, to have your mind be totally clear, to feel the absence of distraction, and to focus on yourself. 

What does it tell you about you, your world, how you interact with the world? What can you learn from this uniquely weird and special experience?

Think about it.

Eventually the power came on and when I looked at the blinking clock I realized I had fallen asleep an hour earlier than normal.  I don’t think it was because I was super tired. I think it was because I was super at peace. Without the artificial hum I only had my body to tune in to and I was filled with notions of creative possibility and what could be. 

I was woken up partially by the one small light I’d left on, but mostly by a giant Whiirrrr of  lights and electronics turning on at once in the general vicinity of my building. It jolted me out of my sleep.

While having power meant I’d be able to call my wife, write this post, and listen to some good music, it also bummed me out. I missed that feeling, that focus, that clearing of my head, what it felt like without the pulsing external energy, having the possibility to look inward to consider what’s possible. It felt pretty great.

The challenge now is how to recapture that feeling. Well, the newscasts reporting the blackout are talking about the possibility of more. I didn’t have any plans to go back to New York, but I might start checking into flights.

Is it possible to only do things that bring you joy?

In this ever-increasingly fractionalized and polarized world, joy is popping up as an antidote everywhere you turn. See the (debatably) magical Marie Kondo, for starters. It’s an amazing time to get your joy jam on and get the most out of every second you spend spinning on this giant rotating orb.

As someone who spent many years basing most of my decisions and actions on if they would bring me joy, I’ll tell you that it’s a spectacular, and extremely problematic, way to live.

About three years ago, my business was humming along and my dad was gently and honorably breathing his last breaths. His death made me think more deeply about my life. I decided to go away for a couple days and take stock of where I existed in the world.

I rented a little farmhouse Airbnb in Wisconsin and walked the woods for a couple days. I created a list of things that brought me joy, and committed to do more of them. The result was immediate: a more fulfilled life, and a more depleted bank account. It was a tradeoff I was more than willing to make. I taught, learned, and mentored. I wrote a book. I taught and mentored some more. I spent more time with my family and walked my dog a lot, too. I was only doing things that brought me joy.  

As you might imagine, most of that joyful activity was immensely emotionally rewarding. Financially? Not so much. The part of my business where people actually paid me shriveled. So I challenged myself to make more money. I got back to business and focused and hustled and righted the ship. But when that ship sailed, it left a lot of joy on the shore.

So what to do? I still wanted as much joy in my life as much as I could get. Where’s the balance?   The answer, of course, was on Facebook. 

I recently asked the question to my Facebook friends: Is it possible to only do things that bring you joy?  Not surprisingly, there were many No’s, with people recounting the menial tasks of life—laundry, dirty dishes, commuting, doctor appointments. Where’s the joy in that?

Ah, that’s where the Yes’s come in.

These were the people who acknowledge the dishes and traffic, but who also know that joy is something bigger than what we do. For example: “Yes, if one learns how to find joy in all things. In other words, the joy has to emanate from the doer, not the task.” And “Joy exists according to the person perceiving it.”

Experiencing joy is about how you see life, not what you have or do.

One person who had faced a serious sickness talked about how she sees life differently now. “I take joy in picking up my dog’s poop, because I still can, and while I’m still at it, I notice the fresh air, and some rabbit crossing the sidewalk, and a guy selling churros…and while I tie that stinky bag, I am joyful in being alive.”

Living a life full of joy doesn’t mean only doing joyful things. If you can find joy not in the things you do but in the way you are, you can find joy in anything. And you’ll be on your way to living a life full of joyful things.

Good luck. I’m going to walk my dog.

Is "Do what you love and the money will follow" really true?

Alice Waters’ culinary empire started with duck and olives.

It was the first meal she served at Chez Panisse in 1971, at the wonderfully ridiculous price of $3.99.

I heard her tell her story on the always awesome How I Built This podcast. She had no business plan and no clue how to open a restaurant, so she just started cooking. That, she knew how to do. She also waited tables on the side to make money, so she could take time to experiment in the kitchen.

She had financial backers, although none of them expected to make a profit. They just liked food.

Now, at her internationally known restaurant, she has two main chefs and they both work three days and get paid for five. That way, not only do they both get time off, but they can take time to recharge their creative brains and come up with new ideas.

Alice Waters did what she loved from the start and succeeded. But that’s not what was the key to her success. Or mine.

I started my marketing consultancy in January 2009. 10 years later, the economic meltdown of 2008-09 somehow doesn’t seem as bad. But it was a bad time, stained by a truly shitty economy. A lot of people lost their jobs. 818,000 in December 2008, when I lost mine.

Some of them, like me, started new businesses. I had no formal business training. and maybe a few little crumbs of business knowledge. “Clueless” would be overstating my level of preparedness. But here I am, over 10 years later, having succeeded with lots of help and support from smart and generous people, and having learned a lot on my own.

Since I’m a writer, I wrote a book about it, called The Worst Business Model in the World: A New Kind of Guide for a New Kind of Entrepreneur. At the core of the book is  the five strategies that helped me survive, and whether she knew it, they helped Alice Waters too.

The first one is called Trust Yourself. It sounds easy. It sounds intuitive. But it’s really hard. And insanely important. Go ask Alice. Or Lara Merriken of LARABAR. Or Niraj Shah and Steve Conine of Wayfair.

When you trust yourself you can try new things, which leads to new ideas. New ideas are the lifeblood of any business. Alice Waters credits the longevity of Chez Panisse with constant innovation, and I can relate. In the past year I’ve developed a Professional Coaching practice, helping entrepreneurs get unstuck from the things that are holding them back and achieve their goals, however big or small.

New ideas stoke the soul and feed the brain. And they fill the wallet too.

So yes, do what you love. But also constantly change. And then, the money will surely follow.

How much money does it take to be happy? $47.

That’s about how much it costs for a good bottle of wine at my local wine store, some nice cheese, a good loaf of bread, and some big fat olives. That’s what makes me happy.

I’m also happy when I’m sleeping on high-thread-count sheets, wearing comfy new underwear, and taking an occasional trip to Italy.

What makes you happy? How much does it cost?

At a workshop I facilitated last week for my book The Worst Business Model in the World: A New Kind of Guide for a New Kind of Entrepreneur, in the very cool and cozy 818 co-working space in Evanston, Illinois, we had a lively debate during the Q&A about what success really is. This question is at the heart of the book and most of my workshops, and was also featured in a recent story in Inc.

Ultimately, what’s really important to being successful is being happy, and the key to being able to call yourself happy is being to be able to define what happiness means for you.

Every person has a different answer, and each person’s answer might change depending on what’s going on in her or his world at the time. Nobody can answer it for you, but maybe I can help a little.

You probably figured this out already, but in terms of long-term happiness, the $47 thing doesn’t really ring true. As someone who’s been around for several decades, I can tell you that the value of imagining where you want to be in the future definitely holds true. If you make and save more money earlier in your life, you’ll likely get to work less later in your life. And vice versa–it depends on what you want. That’s where imagining your future helps. What does it look like for you?

Some people want to retire early to get away from jobs they don’t love or feel fulfilled by, or are working for a paycheck and are laser focused on when they’ll be done. Other people don’t know why they would retire or what they would retire to, since they love what they’re doing now. I’m in the latter camp. I couldn’t retire now anyway, but I like the fact that I’m going to be working for a while because I really like what I do.

I also like going to Italy every once in a while. So I know I need to work hard, make at least enough money to pay all my bills, and have a bunch left over to get on a plane and enjoy the wine and cheese.

How about you? Think about what you want to be doing and how hard you want to be working at it, this year, next year, a few years from now, many years from now. You may find out that olives and cheese sound pretty good and $47 is a perfect number. You may also want to add a couple of zeros, so you can sit in a café in Italy while you’re eating them.

Work less, live more.

I was walking my dog on a cold Friday morning recently and my neighbor was shoveling his icy walk. He told me he was home for the morning because of his daughter’s song concert at school. Otherwise, he told me, he’d be working.

I wanted to tell him, your daughter’s song recital isn’t an excuse to miss work, it’s a reason to miss work!

It’s not that working is bad. Working is good, making money is good, and working to make money is important. It’s how you get to go to Italy once in a while and meet Italians and eat pasta and drink red wine, which in my humble opinion, is really important for humans to do.

But how you work to make money is even more important.

I love the book 168 Hours by Laura Vanderkam. I talk about it often, mostly because of it’s wonderfully simple and life-affirming premise: With a little planning, you can spend time doing the things you want to do without having to make sacrifices. Or excuses.

It’s a beautiful and dangerous freedom. And it’s at the heart of being a UDOT.

When you’re a UDOT you get to spend a ton of time not working, if that’s how you plan your days. But you also need to take advantage of your flexibility, to make the most of every second when you are working, whether it’s at 2 AM at your kitchen table, on a Sunday in your jammies between sections of the New York Times, or in the middle of the day at your co-working space.

Working less is awesome. So is making money. If you like to do both–I know I do–make the very most of the time you work, so you can go to the aforementioned Italy once in a while. Maybe more. It’s a big country and there are endless places to drink wine and eat pasta.

This has been a public service announcement from the Bureau of Working Less As Long As You’re Mostly Working Your Ass Off So You Can Make Enough Money To Go To Italy Every Once In A While.

The biggest co-working boner you can pull

UDOTs love co-working. But there are (sometimes written, sometimes not) rules, and anyone who’s co-worked longer than a few days knows the boners you can make:

• Conducting excruciatingly loud conference calls in common areas while wearing your headphones, having no idea how loud you’re talking. Get a conference room, people!
• Eating someone else’s lunch out of the fridge (the one she was thinking about all morning), or the snacks that aren’t on the “shared” shelf.
• Not putting your coffee cup in the dishwasher and washing your plates and silverware.

Those are the basics.

Then there’s the one that could be the least obvious and most critical:

Not taking advantage of the best resource co-working has to offer. Which is of course, the people.

You’re doing yourself a massive disservice—and wasting money—if, every once in a while, you don’t pick your head up and say “Hi,” introduce yourself to someone, start a conversation.

The worst mistake you can make in co-working is not making the most of your community. Co-working means having great resources sitting within inches of you. If that’s not the case, you’re in the wrong space. It’s definitely true of Second Shift in Chicago, where I spend a few days a week.

Some co-working spaces have great amenities like cold-filtered coffee and craft beer on tap. But you pay the price in your monthly bill. I like the ones that have really smart, accessible, friendly, and helpful people on tap. You can’t put a value on that.

I have nothing against WeWork and other “chain” co-working spaces. Just remember that one of the biggest potential benefits of co-working isn’t the stuff that comes out of the taps. It’s the humans who walk in the door.

Want to get more done in 2019? Get more naked.

How come nobody gets naked anymore?

When I was little my dad had a membership at a downtown Chicago club where he entertained clients. Occasionally he took me to the sixth-floor men’s gym, where there was a small pool and locker room, and where the men practiced rampant, unrestrained nakedness. They walked around naked, swam naked (often the backstroke, unfortunately), played cards naked, drank naked. So it figured that these guys did business naked, too. Not actually without clothes on. They conducted business transparently, although that’s not the way it was described back then. It was just the way they worked.

Remember the steam baths in the movies, where the gangsters had meetings wearing nothing but their pinky rings? The shvitz, as my brethren call it. These days the shvitz is a room where people wait for their next pitch meeting with their next VC.

Is it my imagination or are we more guarded and less naked these days? Without being outwardly creepy, I’ve taken note of pre-and post-workout goings-on in the locker room at my local gym. Their laundry bills must be massive, because the number of towels guys use to cover themselves up would cover the Golden Gate Bridge. What happened to the free-swinging confident culture of putting yourself out there and presenting yourself as is? Seems like we’re covering ourselves up with more physical and emotional layers, which leads to preventing ourselves from digging in deeper to real truths that can make a difference, unearthing more interesting ideas, having deeper conversation, and more meaningful connections.

Friends, it’s time to get naked again. For two reasons, this is the perfect time to get nakeder.

For one, it’s resolution-making time. We simmer with energy and enthusiasm around pacts we make with ourselves. We hope we’ll pull them off but are afraid to admit that we may not. Resolve wisely and nakedly.

The other and more important need for increased nakedosity is the excess strife in our world, which could be directly related to the lack of honesty. It may be making fact-checkers rich but it’s not helping us get along.

So here’s a notion for you to consider. Practice a simple two-word mantra:

Admit shit.

What if we let go of the doubts, fears and biases in our heads and nakedly said them out loud? For example…

I was wrong before, can we start over?
I’m supposed to know the answer but I don’t.
I’m in over my head even though I was just hired.
I don’t know what you’re talking about.
I don’t know how to use (Slack/WebEx/Zoom/Instagram etc.)
I missed the email.
I don’t understand the email.
I don’t have email.
It’s loud in here and I’m having a hard time hearing you. Please talk louder.
I don’t agree with you but I’m willing to try to understand you. Please start over.
I’m not exactly sure what I’m doing here…in this room, on this planet…

The amazingly wonderful thing about exposing yourself and making admissions like these is that every single one of them presents an opportunity to move forward, to open us up to further conversation, a new path forward, a smile, some goosebumps, a great idea we didn’t see coming. In life, at work, in the world.

And of course, apropos to the time of year, a fresh start.

Make 2019 a year of increased nakedness for you. Take on the philosophy of those old dudes in the shvitz, swimming naked on their backs, practicing the most radical form of honesty. Expose yourself, put yourself out there, sidestep the fear and embrace possibility. Trust others to trust you so you can do great things together.

Yes, you can leave your job this year. Doing these 3 things will help.

As the new year kicks in, you may be asking yourself, “Can I leave my job this year? Could I make it on my own?”

You’re not alone.

How many people out there are in a 9-5 job and just not happy, unable to get the job they want but unwilling to take a job they’ve been offered?

How many might not inherently want to be entrepreneurs, but have invaluable talent and experience that they can use to make money and pay the bills?

And how many are ready to start advocating for themselves in a way they never had to before?

If entrepreneurs are known to run a business by the seats of their pants, people who didn’t intend to be entrepreneurs don’t even have pants.

Like me.

And maybe you.

After I was laid off almost exactly 10 years ago (December 2008, not such a good time for our economy), I started a small marketing consultancy called Twist, with no formal business training or experience. But I had a passion to do what I love and help people. I’ve sometimes barely survived, but mostly I’ve prospered. And I wrote a book that became a #1 bestseller on Amazon called The Worst Business Model in the World. It’s a very human and approachable, non-business-y book, written for people I call UDOTs, which is an acronym for Us Doing Our Thing and pronounced “Yu-daht.”

UDOTs work for ourselves instead of working for the (Wo)Man. We do what we’re good at and are passionate about. However, we’re pretty unenthusiastic about—and sometimes incompetent at—the more technical aspects of doing what we love, things like business development, finance, administration, and legal responsibilities.

Does this sound like you? How then can you succeed out there on your own? Start here:

1. Trust yourself. Even in the face of debilitating doubt, it’s important for UDOTS to have ass-kicking confidence in what we bring to every opportunity and have faith that how we do what we do is the right way to do it. When it works—and it will work—you’ll have evidence that you can use in the future to remind yourself that you’ve succeeded in the past. It’s crucial to constantly remind yourself of your specialness and the value that you bring to the world. Don’t think you’re lucky to get work. Think that whoever hires you is lucky to have you.

2. Trust the World. The world wants you to succeed. You can choose to believe it or not, but if you do, it’s much more likely to come true. Regardless of how we imagine them or what we call them, UDOTS have to believe that there are forces at play beyond our control, waiting to help tip things in our favor. Again, if you don’t believe this, it’s less likely to happen. Kevin Systrom, co-founder of Instagram says, “The world runs on luck. It’s just a matter if what you do with it.” You don’t know what’s going to happen. The world doesn’t know either. Believe the world’s on your side and it’s a lot more likely to be something good.

3. Be the First You. When I started writing The Worst Business Model in the World, I told a smart and trusted friend that my book would be kind of a Godin/Gladwell combo. She said, “Why not make it a Schuman original?” That book, that song, that code or system, those documents, those words and ideas— they’re yours. They came from inside of you and that gives them credibility, meaning, and depth. Don’t worry about becoming the next whoever. Focus on becoming the first you.

Can you leave your job this year? Yes you can. Trust yourself, trust the world, and be the first you. I hope these three important factors that helped me succeed as a UDOT help you too.

When did our lives get taken over by three little dots?

You’re hunched over your phone. Staring. Anticipating. Waiting to see what will come when the three little dots stop dancing.

Three dancing dots, making you wait, postponing your life, delaying you from actually doing something, causing you to ignore someone who’s right in front of you, trying to have a conversation.

How much time would you estimate you spend staring at the three little dots on your phone waiting for someone to get back to you? I don’t think MIT has done any studies on it, but my guess would be, scientifically speaking, A LOT.

I recently wrote an Amazon bestselling book called The Worst Business Model in the World: A New Kind of Guide for a New Kind of Entrepreneur. The chapters are full of theories and worksheets to help people I call UDOTs, an acronym for Us Doing Our Thing, the folks who are good at what they do and passionate about doing it, and need some help to build a business around it.

There isn’t a chapter about our lives being destroyed by three little dots, because it’s an awful, negative thought. If I did write a chapter about it, it would be called Stop Staring and Start Doing. Or maybe, Put Down the Phone and Pick Up a Friend. It would encourage you to take a walk, hop on your bike, get on the train or in your car, or go see somebody in person. Celebrate the awesomeness of an actual conversation with a real human.

I’ve learned and practiced a lot of things that have led to my ten years of success as an entrepreneur. Most of them revolve around UDOTs’ scientifically unprovable belief that if you do a certain thing for potentially no apparent reason, something good will come of it. And there’s nothing better and potentially more productive than making a real connection with someone sitting across from you over a cortado or a cocktail, leaning in and actively listening, hearing what’s up in her world, or thinking about who you might connect him to. Laughing, enjoying their presence, taking advantage of every precious second we get to inhabit this planet, talking about things we’re passionate about with people we like. Thinking about the possibilities of where the conversation might lead, professionally and personally, and what might come out of it.

Staring into their eyes and actively listening to what they say.

Looking up, not down.

Paying attention to your friend’s words, not three little dots.

Not waiting on anything, but starting something great.