Archive for Entrepreneurship – Page 4

Entrepreneurship is …

You Have 137 Days Left in 2016: Make The Most Of Them

Numerous times throughout the year (and quarter) I look at the calendar and see how much time we have left to make progress on our goals.

Today, Aug, 17, 2016, you have 137 days left and about 20 weeks to make the most of.

I just put my process in this post but the four steps are simple:

  1. Take an inventory of your time left. You’ve got 137 days left in 2016!
  2. Get clarity on what you want to accomplish.
  3. Identify obstacles to blow up. Obstacles are really opportunities.
  4. Pinpoint the key steps to make next.

This can be used for personal, business, or career or a combination of it all for maximum goal achievement.

Download the PDF Worksheet Here

Finish 2016 Strong: Here’s An Exercise To Help

What Are The Top 3 Things Affecting Your Happiness as an Entrepreneur?

If you’ve been reading my blog for a while, you know for the last year or so I’ve been sharing details about my journey with maintaining good mental health as a entrepreneur.

I’m working on something bigger as part of that. And I’m interested in knowing what other things get in the way of your health and happiness of my fellow entrepreneurs.

Please take a second to share (at least) the top three things you battle as an entrepreneur. 

My New Business Leadership Podcast with Matt Danner

For a couple of months or maybe years, my business sidekick Matt Danner (COO of iThemes) and I have been talking about sharing the lessons and experiences we’ve learned leading and growing a team and business at iThemes over the last 8+ years.

This morning, we finally made actual progress on that dream and recorded the first two episodes this morning of a business podcast called Leader.Team.

In the first episode aka The Pilot, we talk about our backstories and background to where we are today. IN the second episode, we talk about our current roles and responsibilities, how we got here and why we think our unique, distinct personalities and strengths have made for a very successful leadership team.

Here’s some details about what we’re hoping to do with this podcast series:

Goal — To post a short (15-25 minute), easily digestible, practical and applicable podcast, from our experiences, twice a month on topics that young leaders and managers are interested in.

Purpose — To share our experiences and expertise as leaders and managers at iThemes in order to help others who want to lead, grow and care for teams, while also making purpose and profit.

Significance — We’ve learned a lot about leading and managing people as well as growing a business, often the hard, painful, costly way.

Prior to starting iThemes, I was a journalist, having “managed” only a part-time person before starting iThemes.

Matt was a college student when he started at iThemes, initially handling our sales emails, now managing 25+ people, many of whom are older than him.

Now, after 8+ years, we have a team of 25+ people, some in office, some remote, and thousands of customers around the world.

We want to share the stories, lessons, values, beliefs, philosophies, tools and experiences we’ve gleaned over the years to help you learn and grow … from each of our unique and different perspectives.


Go signup to be the first to know when we launch the Leader.Team podcast series here. 

Confessions of an Entrepreneur

This post has been brewing in me for a while, especially since I shared the Iceberg of Life.

This isn’t a rant. It’s not meant to engender sympathy for me. And it isn’t a confession of my own thoughts, doubts, worries, insecurities for therapeutic reasons.

It is meant to help other entrepreneurs know one thing: 

You’re not alone. 

Most everything on this list has been something I’ve struggled deeply with at one time or the other in my time as an entrepreneur, and/or heard numerous entrepreneurs talk about consistently.

I’m not saying any of these are valid or right. I’m just saying they are part of the experience.

Entrepreneurship is tough. It’s lonely. It’s a roller coaster. Sometimes it’s just awesome and other times you’re ready to puke and get off the ride. Overall, I can’t imagine a better gig for me.

So rest assured if you identify with any, or all of these, you’re not alone.

You’re just a human doing a very tough job. 

Confessions of an Entrepreneur

Old wooden confession booth

  1. “I got really, really lucky because I’m definitely not this good or talented.”
  2. “I’m carrying the weight of the world right now, and I’m crumbling under it.”
  3. “I’m anxious and worried all the time. I might have an ulcer.”
  4. “No one really knows or understands what I’m going through or dealing with.”
  5. “No one understands me.”
  6. “No one really cares about me.”
  7. “When people rely on me, I feel good. I want to feel relevant and valuable. But now, everyone actually is relying on me and I don’t have any time for myself and I’m drowning.”
  8. “I’m angry and frustrated all the time.”
  9. “I’m worn out, burned out, and just tired and weary.”
  10. “I feel alone, empty and lost.”
  11. “I’m not worthy of this.”
  12. “I’m unhappy and unhealthy. In fact, I’m quite miserable and most of it is self-inflicted.”
  13. “I loathe criticism. I could close a huge deal, have 3 others closing soon, get 500 accolades from my clients, but that one stupid person’s comments has consumed me all week and I can’t get past it.”
  14. “I’ve got problems and they are huge, and unique, and I’m the only one dealing with them, or who even knows about them.”
  15. “I’m not sleeping at night because I’m worrying too much.”
  16. “I’m the most insecure person in this room.”
  17. “If I fail, what will people think and say about me?”
  18. “What am I anymore if I’m not doing this?”
  19. “Juggling family and business responsibilities is so tough that I just want to crawl under my desk and hide.”
  20. “Sales are down today. Oh God, the world is ending!”
  21. “Will I have a heart attack at 50?”
  22. “This new competitor just entered my space and is younger, better, faster and cheaper. Is this the end?”
  23. “I’m a fraud. I suck. It’s hard to look at myself in the mirror.”
  24. “People think I’m successful. I have it all. But they have no idea of the true cost of it, and that I’m miserable.”
  25. “What surprise B.S. issue or problem or challenge will happen today to me?”
  26. “My back hurts so bad it’s tough to sit in a chair, but I have to work or I don’t get paid.”
  27. “I’m so stupid … I can’t believe I didn’t see that problem or issue until today. And now it might be too damaging to fix.”
  28. “The mistake that I or someone else just made could doom all of this.”
  29. “I need help, but I’m too prideful to ask for it.”
  30. “Everyone on my team should work just as hard and be as committed as me.”
  31. “I’m jealous of everyone else. It’s eating me up that so many other people are doing better than me, even though I’m busting my butt.”
  32. “My friends and family still thinks I should have done X, instead of this. I have no support.”
  33. “What if this doesn’t work?”
  34. “If everyone knew what really goes on inside my head, they wouldn’t want to know me.”
  35. “I don’t have any friends.”
  36. “Would these people be my friend if I wasn’t doing this?”
  37. “Is this as good as it gets?”
  38. “Sometimes I wish I just had a 9-5 job. And could clock in and clock out, and leave all of this at the office, for someone else to deal with.”
  39. “I’m so ready to quit.”
  40. “Someone I trusted deeply betrayed me. I’m pissed. And now I doubt everyone I know.”
  41. “I don’t know how I’m going to pay my mortgage this month, let alone salaries.”
  42. “Sometimes I really can’t stand people. Business would be awesome without the people.”
  43. “All I do is put out fires all day, every day. It seems like problem after problem after problem.”
  44. “I have absolutely no clue that the decision I just made is the right one.”
  45. “I’m down, life sucks, but I have to put on a happy smile for everyone else and act like nothing’s really wrong.”

OK, these are the Confessions of an Entrepreneur, so far anyway, as I’m sure there are more.

Again my goal isn’t to rant or get sympathy or to hurt anyone’s feeling, I simply hope it resonates with those entrepreneurs who might read this and be right in the middle of a tough time.

For you, I hope you can say because of this: I’m not alone. 

And if you’re one of those people in a low time, check out this post I wrote detailing 5 Ways I Deal with Lows in Business here. I hope it helps you wade through to the other side.


If these confessions resonate with you … it might be time to join an entrepreneurial peer group.

I’ve been a part of four entrepreneur groups over the last 6 years and they have had a profound impact on my life.

Check out my new collaboration with Dr. Sherry Walling at ZenFounder called ZenTribes today!

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?