5 Habits for Staying Motivated When Money is Tight

One conundrum that every entrepreneur faces, sooner or later, is the constant battle between doing what we have to do, and doing what we want to do. It is important to do both every day, though not necessarily in equal amounts. We’re all artists. We have raw undeveloped talent inside of us. The development of that talent is ultimately our key to being successful in our chosen endeavors, but it’s usually not a short path to financial success. Most often, the work that pays the most readily is the least fulfilling, at least in the beginning.

Most of us are somewhere in the middle of the spectrum. We all have bills to pay, and we all have a fundamental need to do what we were made to do. The challenge is finding a way to integrate both into one life. In ten years since I left my traditional job, I’ve gained a healthy respect for just how difficult it can be to stay in the game for the long haul. I’ve also experienced how this single factor separates success from failure. While it’s fine and good to say “just don’t quit,” this is much easier said than done. If you don’t know the key to warding off burnout, it’s only a matter of time before you will quit. You won’t have a choice, because your tank will run out of gas.

If your day job is a necessary evil that you tolerate just because it pays the bills, it’s important to integrate a daily practice of some sort of art form, whether it pays or not. On the other hand, you might be brand new to business, struggling to figure out how and where to find clients. If this is the case, you may find your work fulfilling, but not lucrative. In this case, it’s important to integrate a daily practice of asking for monetary payment for any kind of service, whether you enjoy it or not. If you’re retired or financially independent, that’s different in some ways, but not as different as you might think. Even if you don’t need to make money, we all have a fundamental need to marry our skills to something that provides value for others.

Here is what I’ve found to be the fundamental habits for staying motivated when burnout and discouragement threaten to take us out of the game.

Create personal rituals that reaffirm your commitments.

Steven Pressfield, author of The War of Art, says that when he sits down to write, he says a prayer to invoke the Muse. Personally, I’ve found that writing itself is a ritual; I think of it as my personal offering to Heaven. A ritual does not have to be fancy, complicated or elaborate. It doesn’t have to be something that takes a long time. You don’t have to buy anything or designate a space in your house, though you can if you choose to. The critical aspect of a ritual is that it has meaning: it reminds you of your commitment. To what higher purpose are you willing to commit the remainder of your mortal existence? Is it the end of world hunger? Eradicating sexaul assault? Providing education to impoverished youth? Whatever your declared purpose might be, the more often you remind yourself of it, the easier it will be to stay motivated.

Personally, my life’s purpose as I have declared it, is to put an end to discrimination against introverts. To name one example of a ritual, I look at my expired passport every day, and I sometimes thumb through the visa stamps (the one here is from my 2006 trip to Cruz Alta, Brazil). I think about the places I will return to, and how many more places I will go to do my life’s work. It is a reminder that everyone everywhere in every language is affected by personality bias. It reminds me of the enormity of the problem I am up against and how there is no time to waste.

Engage in one-on-one dialogue with live people.

We can’t stay motivated in a vacuum. One of the ways that we keep our commitment alive is to share it, and there are two types of conversations that accomplish this purpose.

One method is to simply “catch up” and say hi. When someone says “how was your day?” or “what’s new?”, the way you answer these questions is important. It’s worth putting some effort into thinking of what you will share before you see an old friend. The stories you bring back from your travels can make a real impact on them. They may realize a new solution to their own dilemmas, just from hearing what you’ve been doing. It’s important to speak from the heart, and talk about the things that make you come alive. It’s equally important to ask them the same questions, and listen with your full presence. If someone has honored you with the gift of listening, you can give them the same gift in return. However, not everyone wants to talk about themselves, especially if they are going through something difficult, so it may be more of a gift just to tell them about your life and allow them to vicariously experience your joys.

The second type of conversation is an offer of an opportunity to participate, such as inviting someone to join a fundraiser you are doing. There’s an art to this. You don’t want to become the stereotypical used-car salesman who promotes everything to everyone, but it’s just as detrimental to never ask anyone to join you. The key begins with creating as many opportunities as possible. For instance, creating a Facebook page for your business and inviting people to follow it is a simple way of allowing people to participate to a limited degree. When it comes to higher levels of commitment, it begins with mastering the first conversation and simply sharing. If you do this well, people will begin to show signs of active interest in what you are doing. They might ask how they can be part of it. The signals might be less obvious, and the key to identifying them is listening. Finally, it’s important to make it easy for people to say “no” or give them an easy way out if they do not wish to participate. That starts with making a decision never to take “no” personally.

Participate in small groups based on shared interests.

Small groups are powerful, because they help to really hone in your purpose. People share their struggles in small groups, once any level of trust develops. They also create easy opportunities to stay connected with people you may meet. I often run into people at events, and I’ll sometimes email them a list of all the groups I belong to. Sometimes, they surprise me by showing up at one. It is especially fulfilling when someone becomes part of a group or community and consequently finds resources that help them. The groups that I belong to can give people access to greater resources than I can provide directly. I might not have what someone needs at any moment, but there is a much greater chance that someone in one of my small groups can help that person more than I can. Meetup.com is a great tool for finding small groups. It can be a book club, an exercise group, civic club or anything else. Personally, I have been a part of Toastmasters for ten years and have recently been working on building my own Toastmasters club. Both of these clubs help me to stay motivated every week, especially because they align perfectly with my core commitment.

Look for “your” people.

For most of my life, I didn’t realize the importance of connecting to my culture. I grew up American, and the United States is a diverse place. There are an ocean of different subcultures that have completely different values here. In 2007, when I hit my turning point and uncovered something that deeply bothered me, I realized that I wanted to help people who were left out of the American Dream. America is known as the Land of Opportunity, but many do not have any idea how to access that opportunity. For most of my twenties, I accepted the idea that I just did not have the personality to be successful. I ultimately came to realize that this was a limiting belief, and that millions of people walk around believing this about themselves and others every day.

My people are the quiet ones, the ones who don’t speak up in meetings. They are often overlooked for their talents and denied opportunity. They are paid less than others who are less skilled and less qualified, if only because they don’t know how to put on a show. These hidden gems are everywhere. Their talents are not put to use. They are often working in menial jobs with great ideas in their heads that they can’t sell, because no one can understand them. Our American culture celebrates extraversion and the ability to appear confident. We systematically punish anyone who does not exhibit this quality. I know my people when I see them. They’re usually downcast, but they’re straining hard to look happy. Sometimes, they’re paid well to do unfulfilling work, wishing they were doing something else. Sometimes, they’re frustrated because their bosses perpetually ignore their ideas. Other times, they’re just grossly underpaid. I see them in all walks of life, in every age group, every race, gender and nationality.

When I meet one of my people, the only thing I do is try to get to know them, and gain a bit of insight into how they are experiencing the problem I’ve seen. Sometimes, I can help directly. Other times, I try to help them find somebody who can. That’s where my small groups play a major role.

Look for opportunities to re-negotiate contracts.

Some people are born with a knack for negotiation. Then, there’s the rest of us. I personally believe that this skill can be learned, as can any skill, and that it’s the first skill every school should be teaching. Our level of success in life is dictated by our ability to to negotiate contracts, both express and implied, written and verbal, binding and non-binding. Sometimes, we’re bound by contracts and don’t have a choice. For instance, children are bound by implicit contracts when their parents are raising them. They can’t leave, they don’t own property and they have to live under their parents’ rules to a degree. However, regardless of how little freedom we appear to have in any situation, there is always wiggle room to be found. We have to learn to identify and use our leverage; otherwise, we are doomed to a life of obeying orders.

Stephen Covey advocates for “win-win” negotiation. I partly agree with him, but sometimes it’s not possible. There are bad people who seek to exploit and think only of their own self-interest. There’s no such thing as a win-win deal with these people. They only think in win-lose terms. They will lie to you and double-cross you at every opportunity, because in their warped view, that’s the only way to succeed in life. When you find that you’re bound in a contract with a narcissist or a thief (or worse), the goal is to exit from the agreement as quickly and as completely as possible. It’s not always easy. See my earlier post about identifying and avoiding the wrong clients. This also applies to employers, spouses and friends. You can’t fix a dishonest person; the best thing you can do is not deal with them at all.

Most of the time, we meet people that we don’t know much about. People are great at putting on false pretenses, so it’s not easy to determine who can be trusted and who cannot. That prospective employee who talked a great game during their 45-minute interview might turn out to be your worst nightmare. The partner who charmed you on a first date might do a Jekyll-and-Hyde 180 and fly into a murderous rage. On the other hand, someone who appears untrustworthy at first might turn out to be the most valuable ally you’ve ever met. In the deceptive game of life, we can only solve this problem through practicing the skill of negotiation. The most common mistake that we make is moving too fast, or trusting people too quickly, before they’ve had the chance to show their true colors.

Negotiation consists of two fundamental components: asking and offering. When you ask someone to do something, they can say “yes,” “no” or “maybe,” and they might counter-offer with something else. For my people, the quiet ones on the introverted side of the fence, the tendency is to not ask for anything, or to only ask for things that are absolutely needed. When introverts do ask for things, their asks tend to be very modest in nature, and this can work against you in more ways than one. If we never practice the important skill of asking for a lot, we never learn how. On the flip side, if we never offer assistance or resources to anyone else, we put ourselves in a weak position because people don’t think of us when opportunities arise.

Part of the negotiation process lies with defining your personal commitment, and exercising the daily rituals to keep that commitment in front of you. When you know your commitment, you know what’s negotiable and what’s not. By sharing those aspects of yourself with others and within your small groups, you empower yourself to leverage resources beyond what you directly control. This creates new motivation, because power and authority give you a new perspective on what you can accomplish. By practicing negotiation, you begin to experience your ability to make things happen with your words, not just your hands.

Motivation is not easy, but I invite you to try out what I’ve suggested here. It will change your life if you apply it.

The Key to Unlocking Creativity

I hear people say the phrase, “I’m not a creative person” all the time. The other variation I hear is “I don’t have a creative bone in my body” or “My sister got the creative genes in our family.”

The misconception is that some people are born creative and some are not. The only difference is that “creative people” have the right habits in place to develop their innate talent. It has nothing to do with genetics, luck, or personality. It has everything to do with habits and commitment.

If you feel you are not creative, but would like to be creative, there is good news. It starts with making a decision to discover and develop your talent, even if you do not know what it is. You will likely remember a time when you enjoyed doing something, like painting or sculpture. Maybe it’s not art; for some people, it’s business or debate. We all have something we were made to do, and it’s hard to be happy without pursuing it.

Your day job and other obligations may not afford you much time to spend on your talents, but even five minutes a day can make all the difference in the world, at least at first. Most of us are busy and deal with constant interruptions. That’s why it is so critical to put systems in place to protect the practice and development of your best and highest skill set. Spending a lot of time on it every day is not required. Consistency is the key. Even if you don’t have much to give to it, giving what you can is the important part.

It’s too easy to get caught up in the grind of paying the bills. Giving up on our talents is not a service to anyone. Refusing to develop our unique gifts because we are “not creative” is a sure-fire way to make ourselves miserable, as well as everyone else around us.

If you are willing to make a decision to spend time each day developing your talent, even if it is not much, new ideas will start to come. Solutions will begin to appear. People are resources will come to your aid. Obstacles will move out of your way.

Make the commitment first, and then you’ll see the proof. That’s the way of it.

Business Spotlight: carolyncrowndesigns

Over the years, I’ve met a number of creative artists who fall into one of two traps: I think of them as the pride trap and the cynicism trap. Avoiding both of these traps is akin to walking on a balance beam. It requires a combination of disciplines that many fail to put in place. Staying motivated requires a healthy balance of enlightened self-interest and willingness to serve. I wish I could say that there’s a magical formula for finding the balance, but there’s not. It just requires practice and experience to build up the skill.

Two Traps

Entrepreneurs who fall into the pride trap insist on doing only the work they want to do (and not listening to what their clients need). They tend to justify laziness by disguising it as righteousness. They live in a fantasy world, where people get to pick and choose what jobs and what clients they take. It often takes a severe financial crisis to provide the necessary wake-up call.

The key to avoiding the pride trap, in my experience, is listening and accepting feedback from others, even when it’s not what you wanted to hear.

Those who fall into the cynicism trap give up on their dreams and resign themselves to working purely for money to the point where the work they once loved degrades into joyless drudgery. This problem is not so easily cured. It is possible to fall into this trap and become financially successful doing something that brings little or no fulfillment.

The key to avoiding the cynicism trap is to devote time each day to doing something you love to do, whether you’re getting paid to do it or not, and block out all interruptions during that time. (Ultimately, the goal is to get paid to do it.)

Avoiding the Traps

For this post, I decided to interview my old high school classmate, Carolyn Crown, who has been running her own graphic design business for a number of years. We’ve loosely kept in touch, and I’ve watched from the sidelines as her business ventures slowly but surely gained momentum. Carolyn is a good example of an entrepreneur who knows how to unleash her creative spirit, while carefully aligning her talent to the marketplace. It’s the critical combination of traits needed to avoid the pride trap and the cynicism trap at the same time.

Dave Baldwin: What made you decide to get into graphic design?

Carolyn Crown: I actually got into graphic design by accident. I majored in communications in college and taking one graphic design course was a requirement. When I went on interviews for PR jobs after graduation, I brought along my meager portfolio from that class. People loved it. They asked why I wasn’t interviewing for design positions. And that’s how it all began. I learned by fire at the first place I worked. It was in-house for a large company with Fortune 500 clients and was high volume, high pressure, high intensity. I like the tangibility of graphic design. That I can point to a logo or a brochure or whatever and say, “Here’s what I did today.”

DB: How do you evaluate new business ideas and decide if they are practical to pursue or not?

CC: Honestly, I talk to trusted friends and colleagues about it. Solicit honest feedback. Not having the ability to devote appropriate time to a new pursuit is common. I have to weigh what I’d be giving up in order to accommodate it. And it’s a tough thing to admit to, but not all good ideas are good business ventures.

DB: Have you found that physical fitness routines have played a role in overall motivation or contributed to the success of your business?

CC: My workouts are definitely my therapy. They’re a constant I can count on when my work or personal schedule is crazy. I always work out first thing in the morning and don’t miss it unless I’m up against a real deadline or a client has an emergency. My fitness is important to me. It contributes to my mental health. Otherwise, I feel like I’d have a really short fuse.

DB: How do you go about finding new clients?

CC: I’m very fortunate in that I’ve never had to find any new clients. My client list has kind of snowballed on its own all by word of mouth. I’ve never advertised. It started with people I worked with years before I only worked for myself. They recommended friends, clients, or colleagues, and it went from there. Referrals by clients are the best, in my opinion. They cost nothing and people love to hire someone who’s been personally recommended to them. The only downside is that it makes it very difficult to turn down work because I’d be saying no to someone who was directly referred to me by a paying client. But I suppose that’s a good problem to have. It broadens my client base, which leads to more referrals. Occasionally, I’ll get a call from a new client who found me on Google. I had someone do SEO on my website, so carolyncrowndesigns.com comes up when someone searches for a graphic designer in Jupiter, FL.
To learn more about Carolyn and see her portfolio, visit carolyncrowndesigns.

Nightmare Clients and How to Avoid Them

This week, I interviewed my long-time personal friend and business ally, Alice Osborn. The video is at the end of this blog post, where Alice shares some of the things that she has learned about weeding out the wrong clients and attracting more of the right ones. She also wrote her own blog post on the subject of how to find the right clients.

It’s been nearly 10 years since I left my full-time job in pursuit of my own business. The last decade has been an incredibly rewarding experience as I’ve had the opportunity to work with a wide variety of different types of businesses. In the beginning, I set out with only a vague notion of what type of business I wanted to create. I knew that I had a knack for writing, and that I could find a way to apply this skill to the business world. As I started to meet with different business owners, I found that a number of challenges seemed to be the same across the board. Top among those challenges was one factor: the need to find customers. A lot of business owners get into trouble by adopting the attitutde that all customers are good customers, and I’ve paid a high price for making this mistake myself over the years.

In the last several years, I’ve gained a better appreciation of something I didn’t understand back in 2007: there are good customers and there are bad customers. Good customers put money into a business. Bad customers leech money out of it. Good customers are fun and rewarding to work with. Good customers are appreciate of great service. Bad customers are disrespectful and offensive. Good customers pay on time. Bad customers pay late (or don’t pay at all).

Unfortunately, it’s not always easy to tell a bad customer right at the outset, but I’ve learned some of the warning signs to look out for. If there is one lesson I’ve learned, it’s that it is never a good idea to ignore a red flag, no matter how small or innocuous it may seem. One particularly horrible client taught me this lesson; the warning signs were there from the beginning. Over a period of months, the situation grew steadily worse until I was ultimately left holding the bag with a large unpaid invoice. It was an eye-opening experience, and I hope to use it to help others avoid ending up in a similar situation.

Here are some things to watch out for when dealing with any kind of client, prospect, employer or professional peer, regardless of industry or budget.

Displaying a negative or disrespectful attitude.

Good clients respect the professionals they hire, and they understand that time is money. A disrespectful attitude can take a lot of forms, but I’ve learned to go by the way it feels to interact with someone. If I read an initial email from a prospect and my gut says “this is trouble,” I pay attention.

Common disrespectful behaviors include:
  • Insisting that we need to meet in person when an email would have sufficed
  • Demanding that I drop everything because you didn’t plan ahead
  • Showing up for a meeting unprepared (or with a different agenda than we discussed)
  • Calling on the phone and not asking if it’s a good time to talk
  • Ignoring my warnings, then expecting me to deal with the consequences when something blows up
  • Acting as if I’ve already agreed to take on the work when I have not committed to anything
  • Getting right down to price, or asking for a discount in the first line of conversation
  • Pretending that you want to hire me for a paying project to get free advice or information

Asking nosy or inappropriate questions.

I’ve had prospects ask me to reveal the names of my other clients, how much money I was making, as well as personal matters like my religious beliefs, political views and relationship status. (I even had one prospect ask me to explain why I was not married.) If a client or prospect asks a question that seems odd, ask yourself if there is any legitimate business reason for them to be asking this question. You are under no obligation to answer everything a prospect or a client asks.


I’ve observed a common pattern with every bad client I’ve ever had: we make agreements to do certain things, and they later act as if the conversation never happened. In one situation, I worked with a client who would send email recaps after each meeting. During one meeting, he grudgingly agreed to something that he was not happy about. This point was “conveniently” omitted from his written recap, which leads right to my next point.

Avoiding written communication.

I once had a client who displayed an odd tendency to reply to simple emails and text messages with a single sentence: “Call me.” I didn’t think anything of it at first, but I eventually realized that this was a strategy to avoid a paper trail. Bad clients do not like accountability, and they always try to leave themselves a back door.
Last but not least…

Breaking (small) promises without owning up to it.

When a client breaks little promises, they eventually break bigger ones. Nobody’s perfect and everyone screws up from time to time. When a good client breaks a promise (such as paying late or not getting information to me when they said they would), they acknowledge their mistakes and do what is needed to correct them. Bad clients try to “slip under the radar.”
The most common example here is no-showing for a meeting, then acting defensive about it. I’ll never forget a situation in 2007 when a prospective client didn’t show up for a meeting and didn’t call or email. I called and left her a voice mail, and she called me back later that day, not even mentioning the meeting she’s stood me up for. I brought it up, and she became angry and started yelling at me. She then hung up and sent me a flaming email. (Thankfully, I never took any of her money!)
Other examples of broken promises include:

  • Paying late, or paying a different amount of money than agreed, without any prior communication
  • Showing up to a meeting with a hidden agenda
  • Asking for a meeting and then canceling it at the last minute (when there was no emergency)
  • Misrepresenting the nature of our relationship to a third party
  • Committing to a specific timetable and budget, then backpedaling and avoiding the subject
  • Attempting to involve me in matters that are not my problem, without my prior consent
Bad clients are like termites. They will eat away at the foundation of any business. They carry negative energy around with them, and they blame everyone else for their own self-created drama. You can’t afford these kinds of clients. They will absorb valuable time and energy that’s better spent with good clients. The best thing you can do is learn to recognize these dysfunctional signals as early as possible. The sooner you identify bad clients, the easier it is to get rid of them.

Pain and Conscious Evolution

One question I have been asking myself, as I notice the pain in my upper back slowly beginning to subside: why is it that things have to become a crisis before they get my attention, and what will it take to interrupt this pattern? Most of the time, opportunity does not wait. The situation with my back has illuminated much about how I manage my life.

Feeling ashamed of poor habits does little to motivate change. At best, shame and fear can create a temporary spike in frantic activity. As soon as the immediate threat subsides, activity settles back down to its previous patterns: in the dead center of the comfort zone.

During certain eras of my life, something was different.

Integrating the Spirit of Christmas as a Year-Round Discipline

I’ve always had a love-hate relationship with traditions. Sometimes, I have looked forward to them. Other times, I have dreaded them and look forward to getting them over with. I have long since decided to stop looking for meanings in things (e.g. the meaning of Christmas) and instead look for new and helpful ways to integrate them into my routines.

Growing up, Christmas was always about getting a week off from school, eating lots of junk food and getting shiny new toys. I remember unwrapping my Nintendo Entertainment System on Christmas morning on 1987. That was quite possibly the most euphoria I have ever experienced during any single day since. Opening The Legend of Zelda in its signature gold cartridge was the cherry on top.

As the years went by, Christmas lost its luster. As my weight climbed toward its peak of 285 pounds, I could feel the effects of overeating sinking in. The amount of available food at holiday gatherings began to feel more like a source of shame as I watched myself demonstrate a complete lack of restraint. The obligation to run out to the mall and buy people gifts began to feel forced and artificial.

There is a different type of gift that we can all “unwrap” this year.

The gift is our ability to tap into our undiscovered potential as sentient beings. (I did not say “human beings” because I personally believe nonhuman animals and plants also have untapped abilities of their own, but that’s a post for another day).

I have not always had a great attitude toward life. It has historically oscillated in reaction to my emotions. It’s easy to have a great day when you’re unwrapping presents in a warm house and not a care in the world. It takes skill to have a great day when something horrible just happened.

I’m now setting my sights on next Christmas (2017), and I’m asking myself, what would I like to be able to say by this time next year? I am no longer setting “goals” in the traditional sense. I do not count any amount of money as success, or any other external “thing.” I am setting personal development goals. By next year, I would like to be able to say that I gave generously all year long to the point where it becomes ingrained as a constant habit.

I’ve noticed that the more I think about “getting,” the more unhappy I become. Ironically, the more I focus on what other people can do for me, the less they seem to want to do for me. On the flip side, when I look back at my happiest moments in life, they were the moments when I managed to briefly forget about myself and focus on someone else. Paradoxically, I think that being less selfish is quite possibly the most selfish thing I can do this year.

It seems to me that the most successful people in life are also the ones who give the most, and this seems like no accident. Zig Ziglar once said, “If you go out looking for friends, you’re going to find they are very scarce. If you go out to be a friend, you’ll find them everywhere.”

As with many ideas, I’ve often found this one quite intriguing, but up until now have failed to instill it as a consistent discipline in my routine. I’ve decided to make this my #1 priority for 2017. I believe that if I get this part right, everything else will fall into place. If I fail to do this part, nothing else will work.

This isn’t exactly a New Year’s resolution, because I haven’t yet identified any specific positive habits to take up, or any bad ones to quit. I’m not sure there will be anything like that. Life is not a formula. It is not always black and white. There are many goals that do not lend themselves to codified rules. It’s more of an art.


And, there’s a week left between Christmas and New Year’s.

And, intention is a powerful thing, especially when it’s focused around something specific.

And, last year, I woke up on New Year’s Eve quietly inspired to give up meat. Which I did, and I have not consumed any animal protein since.

And, I have made powerful life changes several times in my life, all of which have stuck.

So, I now put the question to my own subconscious mind to percolate for the next 8 days. What permanent change, if I were to make it and stick with it every day for the next year and every day thereafter, would slowly but surely shape me into a better friend and a stronger ally to the people I care about?

What might be possible if I stopped trying to “use my network” (I’m just now hearing how selfish that sounds) and started looking for ways to be used BY my network?

What might start to happen if surrender, openness and generosity were deeply woven into the tapestry of my daily habits that they became instinctive?

What might open up if I consistently kept looking for opportunities to push myself just a little — to smile at a stranger when I feel like avoiding eye contact, to say “hi” when I feel like being reclusive, to offer help when it’s inconvenient, to speak up in defense of someone who cannot speak for themselves, to give up a luxury in exchange for a chance to make an impact?

Am I claiming to have done these things on any consistent basis? No. Nor am I promising to always do them in the future. Instead, I’m asking myself the question: what might happen if I did?

Between now and New Year’s, I’m setting my intention on identifying a simple, meaningful and real resolution that I can make and keep (and/or a detrimental habit that I can permanently give up) in line with being a better friend.


The Key to Preventing Stall-Out

I’m a huge believer in doing things strategically. At the same time, I’ve come to recognize over the years that this tendency of mine is just as much a liability as it is an asset. I have learned that when I become obsessed with strategy, my tendency is to do nothing at all. I start to ask too many “why” questions, which creates a cycle of analysis paralysis. Perfectionism sets in. I become paranoid about ways that things could go wrong. My motivation drops off. I start to feel overwhelmed. It becomes a vicious cycle.

Since 2011, I have started and stopped my writing practice many times. I can force myself to get my writing done when it is required for a paying client. When it comes to my own writing (my book, my blog, my next talk), no one is going to come knocking. I can delay endlessly. I’ve learned that I need to create a different type of strategy: a way to guarantee that I will consistently stick to the discipline of writing and putting it out there, rain or shine, good mood or bad mood.

Easier said than done — or is it?

I recently decided not to make any big promises of radically new behavior. I am making no bold promises or declarations. I have found that using accountability to motivate myself is, at best, temporarily useful. Instead, I asked myself a question: do I actually want to write? The answer is yes. Then, the next question is: if I want to write, why am I not doing more of it? The answer is complicated, but it led to a useful insight.

I decided to start writing what I want to write, and to stop caring if anyone reads it or not. That’s when I do my best writing, and ironically, that’s when I’ve gotten my best readership.

Do we still need strategy?


Here’s the thing I’ve come to realize about strategy. Strategy is a mechanism for steering a ship. It is useful for deciding which direction to go, but it is not useful for generating momentum. We do need a strategy, but it is important not to put the cart before the horse. Knowing what direction to go is really not all that useful if you can’t get the car to start. But then again, driving 100 miles in the wrong direction is not productive, either.

There are two common sources of burnout. One results from too much emphasis on strategy; the other from too much excitement. I know what it feels like to think of a new idea and immediately want to dive right in. If you fall into this trap, you’ll burn up your resources before you get the chance to accomplish anything. If, on the other hand, you decide not to pull the trigger and wait, you’re likely to never start.

The happy medium begins with time limits.

Strategizing is great, but at some point, you have to either execute or decide not to. Personally, I’ve found that I need to limit the amount of time I spend thinking about strategy. If I decide not to move forward with something, then I need to stop thinking about it and turn my attention to something else. If I decide to execute, I need to do it within a limited time frame. I can’t spend all day revising and perfecting a blog post or editing a photo. There are too many other things that need to get done.

There is no magic formula and no perfect way to do this. I do not have a 4-step process or a checklist. It’s messier than that. That’s the thing about life. It’s always morphing. As soon as you think you’ve got it figured out, something happens to break the mold. That’s part of why I generally resist the idea of making New Year’s Resolutions. It’s all fine and good to say that I’ll do something every day, but I know myself too well for that. When life throws different things at me, I’m going to change course. What seems like a great habit today may not necessarily turn out to be a great habit three months from now.

Don’t “just do it.” Do think about it. Bounce it off other people and weigh your options. But once the starting gun goes off, it’s time to go.

Resist the Temptation to Re-Launch

As I close out the year, I reflect on the fact that my writing stalled out in 2016. This is not the first time this has happened. Since 2007, the year that I decided to make my writing the focus of my professional efforts, I have experienced several ups and downs with my writing practice. Sometimes, the words come easily. Other times, I feel like I’m pressing against a brick wall. Creating content and sticking with it is not easy.
At times like these, I used to try to fire myself up. In years past, I might have tried to psych myself up by vowing that “next year is going to be different!” Now, I’ve come to understand that this way of thinking is simply another trap, another way of setting myself up to fail. This year, as the New Year approaches, I’m asking myself a series of different questions.
What can I realistically change about my habits from one year to the next, and make it stick?
Last year, I gave up meat on New Years and went vegan a month later. That change stuck like glue. Why did it work, and how do I capitalize on the same principle to better myself as a writer, artist and subject matter expert?
In what ways might I capitalize on the cultural momentum of the season to give myself a slight edge during the month of January?
These are all great questions, and I don’t claim to know the answers. But one thing is for certain; I’m not doing any big re-launch. I am making no big bold promises. If I can find the current, I’ll ride it for all it’s worth. But force of will is insufficient to jumpstart a new endeavor. Excitement doesn’t win marathons. Slow and steady wins the race.
If you’re thinking about your goals for 2017, I would encourage you instead to think about simple and unexciting ways to improve on your core disciplines. What can you start doing a little bit better each day, beginning right now? What time-wasting activities can you make a better effort to catch yourself doing? Can you cut out that extra afternoon snack, that third cup of coffee or reduce your dessert intake by one per week?
I didn’t stop smoking until 2009, when an inner nudge told me it was time. I didn’t plan on giving up meat last year until I woke up on the morning of New Year’s Eve. Each time I’ve ever made a major change in my life, I was guided to do so by a quiet voice that I cannot explain. It doesn’t always happen on New Year’s, but this time of year can be a convenient time if you are truly ready to molt your next layer of skin and upgrade your internal operating system. But you cannot force this to happen. There are things you can do to speed it up a little, but usually not a lot.
Contrary to popular belief, public shame is not an effective motivator. If you want to do a good habit more often, find a way to enjoy it. If you can’t, pick a different habit.
In my experience, re-launches are short-lived, and so are New Year’s resolutions. The bigger the promise, the sooner it is broken. Keep it simple and take it one day at a time.

My First Sales Job—14 Years Later

The Stereotype of SalesIt’s been 14 long, hot summers since I first cut my teeth in my first “real” sales job (unless count my days as a nine-year-old kid pushing a wagon down the street peddling overpriced crap to my neighbors while I still had a couple years of cuteness to exploit for commercial purposes). I was a starry-eyed wet-behind-the-ears freshly-minted salesman working for a certain kitchen cutlery company. During my short-lived and unsuccessful foray into kitchen knife tycoonhood, I learned some fundamental lessons that would ultimately guide me onto my path to becoming The Introverted Entrepreneur.

The Problem

At first, the experience of selling was a horror show. I had to force myself to dial the phone after long periods of procrastination. I would drive out to a remote corner of a parking lot and hope that no one was watching as I scrolled through the contacts list on my cell phone, looking for any excuse to delay the dreaded dials for just a moment longer. When the line started ringing, I would hope for an answering machine.

I didn’t realize this at the time, but the source of my dread and anxiety was not what I thought it was.

See, we were given very specific instructions about how to make our sales calls. The sales trainers had provided us with a script, and in the training sessions, we were told not to deviate from it at all. It was a proven formula, they said. It went something like this:

“Hello (first name), I’m just calling to tell you about this awesome new job I got!” (Wait for congratulations) “Yeah, so I get to tell people about these awesome products that I’m really excited about. I’d love to come over to your house and show you these amazing products! How about 10:00 on Tuesday or 2:00 on Wednesday?”

(Note: we were specifically instructed not to reveal what the products were unless the prospect would not agree to an appointment otherwise.)

Sound awkward? That’s because it was.

To take things a step further, I was advised to call the parents of every kid in my graduating high school class and invite myself over to their houses as well.

For an introvert like me, this job was a living hell.

The Inspiration

I hung up my hat as a knife salesman at the end of that summer, but a seed had been planted. I had made two important realizations: 1) I was capable of much more than I realized and 2) There had to be a better way to sell than what I’d been taught.

It wasn’t until 2007 that the final piece fell into place. I joined a network marketing company and spent six months attempting to sell vitamins and protein shakes. This company used a similar cult-like approach to sales training—insisting that we follow a script to the letter and pitch our product to everyone with a pulse. The seed began to germinate: I would one day create a sales training program for introverts like me.

That was nine years ago. Since then, I’ve been experimenting with numerous ideas, concepts and methods. I’ve tested countless business ideas and spent a small fortune on personal development programs. I’ve worked for a dozen companies and over 70 different clients. It’s been a long, slow evolution that’s led to the first of a line of training products.

The Mission

Currently, I’m co-facilitating the Sharpen Your Video Speak workshop, a training program designed to help entrepreneurs improve the delivery and impact of their marketing message or elevator pitch. On the surface, it looks like a way to learn the skill of talking on camera. In reality, it’s a personal development workshop. See, I’ve learned that it’s very hard to sell abstract ideas. People need something tangible. I decided to use a practical and easy-to-recognize skill as a way of packaging what I was doing. But all along, I have had only one goal: to equip people with the tools to learn to sell effectively without having to endure the cult-like high-pressure sales training rituals that I went through in my days of selling knives.

It’s been an exciting journey with plenty of ups and downs—and I’m looking forward to the next phase. We’re just about to announce our second workshop, and I’m tremendously grateful for the support of my community that has made this possible. More details to come soon!

Adventures in #Podcasting

Over the last month, I’ve been steadily working to build up a personal marketing funnel and an audience. In 2007, I realized a core passion of mine: creating tools and resources to make it faster and easier to introverts to successfully build their own businesses. I have also been studying and experimenting with a variety of business strategies that play well to the natural strengths of introverts. Here is the most recent project I have been working on along these lines.

Thanks to the help and encouragement of Dan Scala and Martin Brossman, I have kicked off a new podcast interview series that I intend to grow into something big. The podcast has a Facebook page and a Youtube channel. Dan, Martin and I decided to do a 6-week series on starting your own business for new entrepreneurs. After we shot the first episode, I quickly came to the conclusion that it made the most sense to focus the overall theme of my podcast on introverts in business. This is consistent with the personal brand I have been building since 2007. I plan to interview a number of different experts and strategic business allies on the show.

Hidden Benefits of Podcasting

Anyone can put together a podcast for next to nothing. A YouTube channel is free, and all you need is a computer with a decent microphone. In a pinch, you can use the webcam on top of a laptop (although this will limit your range of motion). There are a couple of other cool things about doing podcasts that I thought it would be useful to point out:

  • It gives you an easy way to stay in touch with people in your network. Often times, we tend to meet people in networking groups or make one-time contacts at events with folks that we would like to stay in touch with. If you have a podcast, you can invite people to be guests on your show. This creates an easy opportunity to keep the lines of communication open with someone you otherwise might not see again until the next blue moon.
  • It alleviates the pressure of having to present yourself as an “expert”. If you interview other people on a podcast and draw on their expertise, it takes a lot of the pressure off. Don’t get me wrong; it’s still not easy. You still have to be cognizant of your presentation, tone of voice and body language. You also have to watch out for the tendency to use filler words and phrases like “um,” “uh,” “you know,” or “so.” (In episode #4, I noticed that I was using “and” as a filler word when I watched the video.) All that said, though, it gives you a perfect opportunity to focus on improving your delivery without having to come up with all of the content on your own.
  • If you don’t like to write, this provides a different avenue for creating content. Blogging is not for everyone, nor is any other outlet. That’s the beauty of the internet; there are plenty of different tools and platforms.

Podcasting is versatile and flexible, and you can use it in an infinite number of ways. Personally, I plan to focus on bringing a variety of different guests on my show, but you don’t have to do it that way. There are a number of podcasts that function like traditional radio or TV shows, with two co-hosts that appear on every episode.

If you want to follow my podcast, subscribe on Facebook or YouTube. There is plenty more to come!