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Entrepreneurship is …

Confidence Is Comfort

Confidence is defined as “the feeling or belief that one can rely on someone or something; firm trust.”

But simply put:

Confidence is comfort. In your own skin, in your knowledge, in your experience, in your strengths and abilities, and in your resources and relationships.

Whenever I see those things clearly and start building a “firm trust” in them, I see the positive, I see the opportunities and I am more comfortable to step into the unknown and uncertain because they become less so.

Naturally, I then start acting more confident. And my chances of success increase dramatically.

Think about it.

When you’re asked to do something new or unknown, whether it’s a public talk in front of 10 or 1000 people for the first time, or tackle a new project that you’ve never done before or don’t routinely do, you often likely lack comfort, and then confidence.

Uncertainty hits. Fear sets in. And you shrink and stall.

According to Dr. Theo Tsaousides in his excellent book “Brainblocks: Overcoming the 7 Hidden Barriers to Success,” as humans, we actually have four possible reactions instead of just two: “Freeze, Fight, Flight, or Fright.”

“Freeze” is what happens when we hit an unknown, uncertainty or potential threat. We stop and assess the situation.

Then the next sequence according to Dr. Taousides is our “fight-or-flight reaction.” Do we engage or do we run?

And then finally, “Fright.” For a lot of animals in a deadly situation, they will simply play dead. In humans, he writes, “it means doing nothing, taking no action, and just waiting passively for problems to go away.”

For a long time, I thought of this reaction as the “Lettermen’s Jacket Syndrome.” The star high school athlete who has since graduated is stuck forever in the “glory days.” The days when things were so comfortable and confident, he refuses to move on, signifying it by continuing to wear his lettermen’s jacket. Life was so awesome back then, he had mastery, support, and accolades, and the motivation to become better risks all of that comfort.

Success got really cozy, too cozy. New success doesn’t seem as easy, in fact, it’s daunting. Anything new became a threat, unknown and unfamiliar, casting huge doubts, and rather than take new chances or risks, he choose to “Refreeze” in his jacket.

See how it’s all about comfort in the situation?

We lean on our knowledge, our abilities, our experiences, in which we were successful in the past, and if we come up short in the new situation, we are uncomfortable because we don’t know how it’ll all pan out.

Those experiences are so often painful it freezes us.

Think about the word Comfort for a moment and what it really means to us ….

Comfort is: freedom, a sense of security, a sense of knowing or knowledge, familiarity, feeling ready, having assurance, and boundaries with a situation.

Now look at Discomfort.

Discomfort is: pain, unease, awkwardness, unfamiliarity, danger, threat, dread, fear and uncertainty.

And we know it from experience, when you’re comfortable in a situation, you’re naturally more confident. And I would argue, more successful.

Why do sports teams often play better in their hometown stadium, with their familiar hometown fans, then on the road?


When you’re not comfortable, you’re often not at your best. You don’t approach that girl on the dance floor. You hesitate to walk into a room of your peers boldly. When you go for that pass, you’re unsure what lurks on that side of the field. Or you doubt yourself and don’t make the bold ask that would close the deal.

We don’t like to be uncomfortable and so we stall, or retreat, because it’s naturally wired in and identified as a threat.

So the question becomes … in any new situation, any new goal, in any new experience …

How do I become more comfortable in pursuing new goals, projects or tasks?

Here’s how I personally approach it getting comfortable and confident for any situation, and thus answer that question:

1. Clarify the Goal.

The key starting question is:

What goal or objective am I seeking or have I been given?

Clarity is essential here. You’re not seeking to give yourself more reasons to lack confidence, you’re simply assessing the situation so you can get a plan.

Zig Ziglar said: “Lack of direction, not lack of time, is the problem. We all have twenty-four hour days.”

We need to know at least a general direction before we can get there.

Sometimes, I’ll admit, this doesn’t happen as fast or clearly as I’d like. Sometimes I just know a general theme, or direction. But the summit is cloudy. And as time passes, I’ll start to see the peak in between the clouds, and know where I’m going more fully and clearly.

2. Mind the Gap.

Once you’re as clear as possible on where you’re going, you need to figure out who you need to become to get there. It’s time to identify the gaps so you can start the bridge and build comfort and confidence so you can achieve your goal faster and better.

So ask yourself:

Where are the gaps in my knowledge, experience, strengths, abilities? and How do I bridge that gap?

Gaps aren’t bad. I believe anything that stretches you, builds you.

Although seeking your gaps doesn’t  feel good at first, they are opportunities to create a new you.

“Every next level of your life will demand a different you.” –Leonardo DiCaprio

Like building software, I’m always seeking to improve myself, one iteration at a time …. and that only comes with building and releasing new versions of myself.

New challenge, projects, tasks help me to do so.

Without gaps, I’m just sitting still. I’m plateaued. And yet, I’m not satisfied to stay in one place, and hope you aren’t either.

Sitting still only builds in comfort for the present and status quo and erodes confidence. And there’s no progress happening if you’re eternally at a stop sign.

3. Affirm What You Have.

Start by reaffirming what you do have. Reassess and reaffirm the unique experiences, knowledge, strengths and abilities, resources and relationships you currently possess to help achieve your goal.

Let’s take them one by one …

Your Own Unique Skin

Who am I? What makes me awesome?

This is foundational. If you’re aware of who you are, and comfortable in your own skin, you’re going to be more inclined to feel confident as a starting reaction, instead of retreating. Self-awareness, then self-respect and affirmation are critical to progress.

I’ve found the book The 6 Pillars of Self-Esteem, and the sentence-completion exercises in it, to be invaluable for this foundational starting point to build my sense of self-worth and confidence.

Your Knowledge

What do I know already? What training do I have? What have I learned already to build on?

Your Experiences

What have I already done? Where have I gone before? What is applicable to this goal or project or task?

Your Strengths and Abilities

What are uniquely gifted to do and what are your strengths?

I’ve used personality and strengths-based tests to help learn more about myself (and often the things I’m naturally good at and thus discount).

The best discovery tools for this I’ve found are (in order): Kolbe Index A, Strengths Finder, and Myers-Briggs (Keirsey Sorter). Know yourself better helps you take inventory of what you have internally to accomplish your goals.

Your Resources and Relationships

What crucial resources do I already on hand that could be used for this?

Who do I already know who can help me?

Merely affirming the things you already possess that can help you will give you some level of confidence boost.

4. Start Learning and Growing.

Now, it’s time to start identifying the most impactful areas where you can learn and grow to become who you need to become to attack and accomplish the goal.

What things do I need to learn and grow to achieve the goal?

And how and who can help me do that?

Make a plan for what you need to learn so that you can become more comfortable and confident.

By the way, one of the ways I increase my comfort and confidence in public speaking is through familiarity. So before almost every talk I give, ESPECIALLY if it’s in a brand new place, I try to sneak into the room before hand and get a feel, or comfort, with the room.

I’ll go to the previous talks in that room even if I’m not interested in the topics. I try to get on the stage and walk around. I envision myself talking, looking into the audience. I see where the boundaries are on the stage. Are their lights shining in my eyes? Where will my laptop be for slides? Where are the cords I could trip over? I find the A/V techs, and I ask to see and test what mics I’ll be using. I ask them to test my slides well before my talk to make sure they work.

I’ll try to cross off and feel comfortable with all the things that could possibly go wrong (or have in the past). I want to be fully prepared, and thus extremely comfortable, when I’m on stage.

I want the whole thing to feel like my home turf. Like I’ve been there before, minimizing the threats, so I can focus on the impact.

Comfort breeds confidence.

5. Act. Go. Start. Begin. Experiment. Launch. Build. Create. Move.

However …

We don’t create confidence in theory. We create it with action.

This is the vital last step in building comfort and confidence.

In order to create new experiences and confidence, you must act.

If you only Affirm and Learn, but don’t Act, you’ve not moved. You’re still stationary.

 For building comfort and confidence, action is rehearsal.

Only action allows true confidence development.

My best example of this is with public speaking. It’s often the top of the list of freezing phobias people have. After years of public speaking, I know nothing helps with my comfort, confidence and success like PRACTICE. Each time I speak, I learn something new. Start with a small group, then get comfortable there. Then stretch yourself again with bigger and bigger opportunities and audiences.

Last March, I spoke to 300 of my industry peers about mental health, being extremely vulnerable and opening up about my depression, my failures, my low times. That one experience is invaluable to my comfort and confidence in doing so in the future. I can safely tell myself that if I can share that openly and honestly about my failures and dark times, then I can do so again and again and again.

I’ll be building on and using that experience to do it again, and share with a broader audience when the time comes.

Without action, you can’t learn and grow. You’re simply assuming you can or can’t do something, with no proof.

Action builds on your existing experiences, abilities, knowledge to create more comfort and confidence. It shows you what’s possible. It helps you discover things you hadn’t considered or thought about and allows you to get better as a result.

Action is a confidence snowball.

The more you learn and do, the more confident you’ll become. Experiences, knowledge and yes, failures and success build the snowball of confidence.

This is one of the reasons we try to get new team members an instant win when they start with us. We try to give them a small win, that they can then build on later with bigger and bigger wins that increase their comfort and confidence.

Yes, you’re likely to hit bumps in the road and have to reassess, regroup and act again, but you’ll have moved forward in the process.

By the way … here’s an important perspective shifting belief to start chewing on for that:

Failure is learning.

Mistakes are learning.

And it’s only failure if you don’t learn.

You act to find out, to learn and grow, to expand yourself. NOT to give yourself another reason not to stretch and try.

But action allows you to transform new, unknown territory into a familiar one. Actions purpose, beyond learning, is comfort. So that the next time you can operate with more confidence and strength.

For further reading and motivation on Action, check out the Click Publish Moment here.

6. Rinse, Refine, Repeat.

Finally, after you’ve taken action, you’ve learned something new, gleaned new experiences, hopefully expanded your familiarity and comfort, it’s time to rinse and repeat.

By repeating it again and again, you build more and more comfort and more and more confidence.

Now, get started on building your comfort and confidence today!

What are you uncomfortable doing? How can you become more comfortable doing it? And then once you’re comfortable … how can you get uncomfortable again and build more and more confidence? 

No Blame Necessary

I don’t like blame.

Blame has such a harsh, negative and unproductive feeling for me. And it too often appears in team or group interactions.

Blame is “assigning responsibility for fault or wrong.”

In a courtroom, blame is essential. I get that.

But in the workplace or in any team environment, where fallible human beings are attempting to work together to ship projects and meet milestones and do good, I’m increasingly ready to stamp it out altogether.

Blame’s gotta go.

And here’s why:

  • It gives us an unproductive focus — We waste time dwelling on failure, negativity, and trying to assign personal responsibility, instead of the action necessary to fix it or remedy the issue.
  • It wastes our valuable time — We take on and are consumed in the negativity, while the fire burns. Mistakes can and will happen. But I’m more interested in using our time on learning and progress.
  • It affirms the wrong mindset — People make mistakes. We’re not perfect. Mistakes are learning. Failure is learning. And when we have the Blaming Mindset, we miss the learning. Let’s instead find the takeaways and move on so we don’t REPEAT those mistakes.
  • It sets a bad tone for our culture — If we have a Blaming Mindset, we won’t take chances or measured risks on new and innovative ways to do things or new ideas and projects. We won’t grow. We’ll wilt. I’ve seen it in numerous organizations where great people, with great ideas, are frozen, instead of freed up to do what they do best.

Let me share a personal experience that could have easily led to needless blame …

Almost 6 years ago, we had a catastrophic server crash. And we didn’t have a backup. Sites were down or lost.

Someone made a mistake.

But as soon as we identified the problem, our team turned their attention to try to find options to fix the problem.

We had two simple choices: Blame or Act. Thankfully we choose to act.

We could have spent time wallowing in the blame, but instead we made progress. Sure, someone owned up to the responsibility. In fact, when we figured out the problem, we knew almost instantly who was responsible. And if no one takes ownership of the mistake at some point, then you might have much bigger problems.

Good, passionate, caring people will always own up to their mistake. Which makes it so much easier to say, “OK, NOW … let’s fix this together.”

But the simple fact is most people will beat themselves up so much that adding to it is just kicking a person while they are down. It’s not productive, or positive, or helpful.

I don’t know about you, but I don’t relish helping someone wallow in their own misery.

What I do cherish is helping them discover and see the lessons they learned from the experience.

And out of that experience, we learned … and we also realized there was a need to have a holistic backup plugin for WordPress that we now call BackupBuddy.

If we didn’t have that painful experience and then learn from it and use it to improve, we’d have missed out on an essential product that has helped thousands of people not make our same mistake, and as a company have enjoyed great success from.

If we’d focused on blame, fostered a culture of blame from that, I’m confident we’d have missed out big time. And we justly should have missed out because we’re more worried about pointing fingers, than solving the problem and learning from it.

By the way … this doesn’t mean I encourage making the SAME mistake over and over again. That simply demonstrates a lack of implemented learning. That’s expensive misery. In that case, someone missed the lesson and repeated the mistake. Someone didn’t show up for class or isn’t a student.

So WHEN, not if, our next mistake, or problem, happens, I try to help us remember:

No blame necessary, just action and learning.

My Time Isn’t Just Invaluable, It’s Irreplaceable

The older I’ve gotten, the more I won’t just give my time to anyone who asks or pushes anymore.

I’m very generous with sharing my experiences and expertise.

When asked to speak, or when I write like this, I’ve sought to be more and more vulnerable and transparent in order to help people. Sharing openly what I’ve learned. With the minimal return of knowing I made someone’s life better or easier.

I’m generous with my contacts and relationships. Likely too generous sometimes. If you’re a friend, and I can help you by introducing you to a mutually beneficial relationship, I’m fast to do so. In fact, I love introducing good people to each other just because they are good people who can do good things together, most often without me.

And for so long I was VERY generous with my time. And because of that, I allowed others to dictate the use of my time.

I got run over. I got taken advantage of. I spent time with people or sat through meetings where I literally felt the life draining out of me. And other times I was absolutely horrified and embarrassed to be in the presence of people who didn’t share my values.

Now I’m greedy and stubborn and insanely protective of my time.

Just because I seek to be supremely generous with so much of my life, doesn’t mean I give you free reign to my time and calendar.

So much so that I don’t have voicemail on my phone any longer. I figure if you need to get a hold of me and have my cell phone, you can text or email me, my preferred method of contact.

I usually don’t take blind appointments, without context and expectations, or those that drip of an obnoxious sales call. Just because you call me doesn’t obligate me to answer or return the call.

And I protect our team’s time too. We do that by locking our office up tight, don’t have our business name on the front of the building and have a doorbell that only rings to our executive assistant, who serves as our bouncer (we call her Painkiller).

You get my time generously if … you’re my wife, my children, my team, my partners, my family/friends, and my customers (in that order).

I prioritize those relationships first, so they get dibs on my time. Anything leftover likely goes back to another group in that list.

I’m not a closed door though … you also get some of my time if you’re a good and decent person who wants to learn and grow, and help others.

Here’s what I’ve learned about those who don’t deserve my time …

  • If you’re only seeking your best interest, and not mine or others, I have no time for you.
  • If you want to filibuster and talk the entire time (in particular about yourself), I have no time for you. I reserve those things for videos, talks that I choose to attend.
  • If you only want to use me, exploit me or others, I have no time for you.
  • If you don’t respect my time by actually showing up and being on time, I’m likely to give you one or two strikes, then mark you off.
  • If you treat the others in my life as trash instead of treasure, I’ll discard you too.
  • If you don’t respect healthy boundaries, I have no time for you.
  • If you’re unkind, rude, hateful, belligerently and unrightfully angry to me, I will boot you.
  • If you’re unkind, rude, hateful, belligerently and unrightfully angry to OTHER people, especially the ones I listed above but also to strangers, I won’t spend time with you.
  • If you don’t share the belief that we’re all created equal but different, I’d rather substitute you for one of other 7+ billion people on the planet who does.
  • And finally, if you don’t give me good expectations for what you want to talk about, what your goals and mission are, for you’re seeking to help, how long you want to talk about it, and then without my consent go over time, it’s likely going to be really tough in the future to have a follow-up with me.

Try to get my time like that and I’ll say: Ain’t no one got time for that.

And this isn’t me saying I’m more important than anyone else, or even trying to rant or complain … it’s merely saying, I possess and am the steward of a limited resource that I don’t intend to squander what’s left of on those who aren’t worthy of it.

It’s also sharing what I value most (the opposite of the ‘Ain’t Got Time For That’ list). And who I’m striving to be as a human being, dad, teammate, leader, entrepreneur, and friend.

And, yes, if you get upset about all of this, then you just self-selected yourself out …

So thanks for saving me time.

For those of you who are on the list, or share my values but aren’t currently on the list, I can’t wait to share my time with you.

How about you? How are you managing the scarcest, non-renewable resource you have? And specifically who or what do you have in your life that’s pirating your precious time? And how do you scrub them/it out?

Carry Your Own Bags

One of the amazing takeaways I’ve had from my experience in the Oklahoma chapter Entrepreneurs’ Organization (EO) is a saying I’ve heard often:

Carry Your Own Bags

The idea is … what you get out of the experience is what you make of it.

Your experience, happiness and fulfillment is your responsibility. Period.

It’s particularly appropriate within a group of successful entrepreneurs, but it applies to the rest of life as well — from your career, your business, traveling, or doing anything new or novel in your life.

And the effect of this advice has been profound for me — revolutionizing my life and business as I’ve actively employed it.

It forces me to say in any experience:

How will I make the most and best of this?

For instance, we have two toddlers. At one point, they were both in diapers. Sometimes, saying no to a toddler is an experience in hostage negotiation.

It’s tough, physically draining, emotionally exhausting work at times.

One would start sleeping through the night while the other was waking up. Or one would get sick. And then the other would too just as the first was getting better. Or it would rain and we couldn’t let them out in the backyard to burn off some energy. Or [insert every excuse to have a bad day and blame it on someone or something else here].

(Right now, if you’re thinking I was acting like my toddlers, you would be correct.)

And through it all, my wife Lindsey would often say … they are only this small for this time, let’s enjoy it.

To be honest, in the midst of a tough day, I didn’t want to hear that. Instead, I wanted to wallow in the misery of it. And ultimately, deep down, I wanted someone else to carry my bags, my responsibility and fix everything instantly so I could be happier.

But slowly I started realizing how right she was … and I said to myself: I must own my experience. I must make the most of it. Indeed, one day they will leave our nest and I’ll crave having them sit in my lap while I read a book to them.

My thinking, my attitude changed. For the better. And so did my experiences with them.

Now that doesn’t mean we don’t have bad days still. But it totally reframes my experience of it and seeks to move the needle from negative to positive.

Barbara Bradley Hagerty says, “Your thinking is your experience.” And she writes that experts claim 30-40 percent of our experience is what we think about it.

With a slight tweak, this is how I think about Carrying Your Own Bags now:

Your Attitude Is Your Experience.

I’ve done numerous things with a poor and negative attitude and made it worse for myself. I clouded my thinking to only see the bad. And in turn, I’ve spoiled countless experiences in my life as a result.

Bring a terrible attitude into the experience and the likelihood of you having a bad experience is pretty high.

You get what you put into it.

In fact, I’ve written before about how I changed my thinking and approach to attending an annual conference for WordPress entrepreneurs changed from terrible to awesome in one year.

It was all my attitude and approach.

It was completely my responsibility and fault that I previously had a bad time. No one could (or should have) made me happier, because that was totally on me.

So I took a step back, realized if I was going to keep going (my choice by the way), I needed to make some major adjustments.

Since doing that, now I thoroughly enjoy the event and it’s on my “Don’t Miss This” list every year.

Night and day difference … just by my attitude and approach.

So now with any experience (new or otherwise) I seek to switch my attitude from negative to positive. I try to reassess how I could be happier in the midst of a formerly bad time or event. I seek to be more open and flexible. I set aside my bias, past bad experiences and frankly, crankiness, and look to the brighter side and be productive and positive with my time in any experience.

I say to myself: “This is my day. This is my time. How do I make the most of this?”

This is my life. This is my time. And I’m going to carry my own bags through it.

What experiences are you expecting others to carry your baggage through?

What attitudes and approach could you change today to make your experiences better?

And then think how changing just a one thing — your attitude — could drastically make everything look and feel better.

It’s a better way to live.

What To Do When Business Sucks

Just wrote a long post sharing the mental processes I’ve used over 8+ years of entrepreneurship for dealing with the lows, the downtimes of business (and life) titled “5 Ways to Better Manage the Lows in Business.”

  1. Know You’re Not Alone.
  2. Acknowledge Your Brain Distorts Things.
  3. Reset the Defaults to Hope, Optimism and Confidence.
  4. Be Lucky and See Opportunity.
  5. Now, Get Back to Working Your Tail Off.

Read the full post 5 Ways to Better Manage the Lows in Business at the iThemes blog.