30 Days of Clicking Publish Business

What Do I Want?

This is the question I’ve been asking myself for the last two years solid, or since I officially entered mid-life.

And it’s been a struggle. 

A couple years ago, I felt like I had hit the mountaintop. The summit.

Seemingly overnight, I felt like I had checked off all the most important dreams I had in my early life and way more.

And in a shroud of guilt, I was asking myself:

Is this as good as it gets?
What’s left? 

I like to always be striving toward something. I’m an achiever. And I had a hard time thinking how life could be better.

Then I left the company I founded and embarked on my next adventure.

Which exposed the fact that I didn’t have a CLUE what I wanted.
I just knew what I DIDN’T want.

And so I have been on Search for my next Wants.

It seems like there are a couple of options about Wants … with definite pros and cons, and appropriate times for both:

  • Knowing what you want
  • Knowing what you don’t want
  • Not knowing what you want

But they seem to go hand in hand …

Some Benefits of Knowing What You Want

  • Confidence
  • Clarity
  • Focus
  • Energy

The Takeaways of Knowing What You Want

  • We are wired to want and crave certainty. Certainty and confidence in that certainty feels safe.
  • Knowing what you Want is contagious. Having confidence in what you want gives others confidence in you. We all want to follow others who have clarity of vision and mission and alignment with our beliefs, values and mutual Wants. It’s energizing.
  • Heading in a Direction without the precise destination gives flexibility and allows serendipity. I did not know I would love running a software company that did backups, security and maintenance. But I loved leading a team and making people’s lives awesome. I followed a direction and found an amazing adventure I couldn’t have dreamed of. I adored the Serendipity. It was better.

But as I’ve shown I don’t always know what I want and have had to go in a search to find this new round of Wants.

A Word on Knowing What You Don’t Want

I seem to be good at knowing some of what I don’t want. But it’s something and they provide some good clues.

Knowing what I don’t want is at least a starting point to knowing what I really want.

Some Takeaways of Not Knowing What You Want

  • Knowing requires a Struggle of Time and Testing. So many times I wanted to say it requires suffering because I’ve felt like I’ve suffered through Not Knowing.
  • In the moment, Time and Testing feels sucky. I’m not very patient. I have built up an aura of expectation that things just come to me (with hard work). And with hard work, I can speed up time. But I’ve had to learn to BE when I can’t DO any more. To just sit. To do what I can, and then at the end of what I can do … wait. I have a whole bag of cuss words to describe my feelings of that.
  • When I look back, I HAD to go through the Journey of Struggle. It’s true of every hard time I’ve ever had to go through in my life. The Struggle, the Storms were what made me … prepped me … for the next Journey, the next significant Life Upgrade and the next level of Wants. I had to go through them in order to get here and go there — where I Want to go next. I had to be seasoned, I had to sit, walk, sit, walk, sit, sit, sit, walk a little. The universe was seasoning me. I had to sit on simmer for a while. (Just don’t tell me this while I’m in the Struggle!)
  • The Journey requires being OK with being Uncomfortable. It means acceptance. It requires the beginner’s mind. It requires feeling exposed and raw and vulnerable. Feeling like you have no control.
  • As we get older, we crave certainty and comfort more and more because we feel we already PAID our dues. Our expectations change because we’ve gotten through to the other side. For example, 10 years ago or so, I did the 7-day, 80+ hours a week work. Early mornings, late nights, waking up in the middle of the night. I did the grunt work, the shit work. I made crap for pay. I took orders. I answered emails. I responded to support inquiries. I made all the embarrassing mistakes and slip-ups. I’ve spent the time with egg on my face and gotten dirty in the trenches. Something inside me goes, “You earned the right to NOT do all that crap.”
  • Thinking you have Paid Your Dues will hold you back from your Next Best. It causes all kinds of issues, but it stunts your growth. It warps your expectations. And it further prolongs your Journey and the Sitting, Simmering, Waiting.
  • Bonus: That thinking is also selfish, arrogant and elitist. You’ll find yourself thinking and doing things that aren’t you. It’ll poison your dreams, decisions, progress and most importantly relationships. Reminder: You have not arrived, Cory. You’re always in motion and growth.

I don’t like to have or even acknowledge regrets …. but I have regrets about this season of my life in the Journey of Struggle.

Every part of the journey has a takeaway.
Even the sitting, waiting times have a gift inside for your Next.


This post is part of my 30 Days of Clicking Publish

30 Days of Clicking Publish Business

Deciding What Game to Play

Not everything is a game but it’s how I think and approach business and work.

And business is the best game I’ve found to play.

This week I’ve been thinking deeply on how to decide when to keep going or quit related to my various business projects.

And I had an epiphany:

I don’t play games I can’t win.

I only play games I have a realistic and reasonable chance of winning at some point. Even if I lose a lot. Just the prospect of knowing I could win. I could break through. Seeing and tasting that I have the chance is so key for me.

I also don’t play games I don’t understand.

I don’t play games that involve primarily luck or chance.

I want skill and strategy games where I’ll likely be changed and transformed through it.

I also only want play my own games.

And play by my rules.

As you can see, I’ve been spoiled rotten by entrepreneurship that way.

Business is indeed a game with a steep learning curve. But clarifying all of these things about myself has been so key to prioritizing tasks or staying with something, or quitting.

Because when the game becomes someone else’s game, played by their rules, with little chance of winning, I am absolutely miserable. And make everyone around me miserable too.

(Even if the game creators and keepers are super nice and it’s a well paid game, like after my company’s acquisition!)

So I must play my own game to be happy and fulfilled and ultimately successful.

Additionally and most compelling to me are the Game Tokens required to play the game:

  • Time
  • Focus and attention
  • Energy and effort
  • Money

All games have an opportunity cost.

To help clarify the games I should be playing, here are some criteria for creating my own game and win:

  • Can I make a deep impact and transformation in peoples lives?
  • Can I make money doing it?
  • What’s the investment/cost to play? See Game Tokens above.
  • Can I clearly see how I can contribute? Can I uniquely use and leverage my experiences and expertise, strengths and interests? And can it be seen and effectively measured?
  • How intrigued and fascinated am I by it?
  • Can I continuously learn and grow? Will it stretch me?
  • Do I have a healthy dose of hope and optimism about it?
  • Does it have numerous benefits? Meaning can I use learning and the work for other things outside this project?
  • Do I like and care about who I’m playing with and for?
  • Am I excited? How much?
  • In the whole scheme of things, how much do I really care about this?

What is your ideal game? What’s your criteria?


This post is part of my 30 Days of Clicking Publish

30 Days of Clicking Publish Business

Help Your Clients Eat the Elephant Too

Over the last couple of years I’ve gotten to reengage with agencies and freelancers for key services for my projects.

And that’s given me a renewed and updated perspective on client services type work.

I have all kinds of empathy about those who do professional services. Truly.

I served a huge group of you for 10+ years and now do so through Post Status as well.

But I have a big suggestion/recommendation for you ….

Tthe other day, I was interviewing Jennifer Bourn, who preaches and teaches on her Profitable Project Plan, and she was sharing her impressive onboarding process alone (9 days of emails prepping you for a bigger ask).

I saw how good the Client Experience could be. (Wow, Jenn, wow!)

And it made me think about today’s post and urging to those of you doing client services ….

Be sure you’re helping and coaching your clients to eat the elephant too.


It’s important to remember … most of us are juggling 15 other “internal” projects and tasks.

We’re choosing you because we think you can take a load off of us — not put a gigantic one BACK on us.

We are in essence seeking to pay a premium to delegate work TO you, not vice versa.

Now, before you flame me … I readily acknowledge there is SOME work, no matter how good your process is, that we as clients HAVE to do. Totally get that.

From logins, to goals, to context and vision and more.

But it’s likely through your client work, you see your clients getting tripped up or held up, not returning your emails or finishing what you need to move forward.

In this context, these are the Big Client Asks.

There are likely some key things but big things that you need from us that would g0 10 times better for all of us IF … you helped us eat that elephant.

COACH us. Educate us. Walk us through it.

AND most importantly, give us bitesize chunks

That could mean …. jumping on a quick call or sending emails that prep us to start thinking about the Big Ask (think Jenn’s 9 emails before the form).

Chunk it up.
And coach us up.

Promise you everything will be better because of it.


This post is part of my 30 Days of Clicking Publish

30 Days of Clicking Publish Business

What’s Your Next Step?

It’s almost comical to say but I’m busier than I’ve been in years. Each week I’ve got multiple live webinars, partner/team meetings, coaching meetings and connecting with others in the gaps.

But that was all intentional when I left iThemes as I knew I needed to “keep myself out there.”

I knew I’d have the tendency to not reach out and talk to people so I built all of it in.

The problem is I now need more margin in my calendar for deep work. Also I’ve dropped some balls and procrastinated on some thing going from Zoom to Zoom.

In my need to get more efficient while ensuring important things aren’t dropped, I’ve been working on my Trello board with my wrangler Karen, who is an insanely organized professional, which is why I hired her.

I’ve had a to-do list for work as long as I can remember. It’s essential for any professional to keep track of tasks.

The past couple of weeks as Karen has essentially been coaching me on optimizing my personal board she mentioned a great tip/hack I’ve added to my workflow:

When you put an item on your to-do list, put a semicolon after it and list your next step.

For so long I’ve been doing step one:

Record my to do’s so I get them out of my head.

But this second step is really incredible.

Too often when I’d return to my list to gauge priorities and tackle them I’d have to do more thinking.

Sometimes I’d just be overwhelmed.

But taking a brief moment to ask, “what’s my next step with this item?” has sped me up, helped me prioritize and truly “eat the elephant.”

It’s one new upgrade that I think is going to stick for the long term.


This post is part of my 30 Days of Clicking Publish

30 Days of Clicking Publish Business

Competing Against Amateurs

If you’ve been in business for any length of time, particularly offering your services as a freelancer, you’ve undoubtedly heard a prospective client say something like this:

I know someone [typically a young relative] who can do [what they think you do] for [less money].

As someone who once offered services as a web designer and served freelancers for over a decade, I’ve heard this story hundreds of times over the years.

A startup entrepreneur I know recently shared a similar response from a prospective client for her services (which we’ll say is web design services), which prompted this post.

My QUICK reply back to her was ….

  • Does “someone” know and keep up with HTML, CSS, browsers, devices? Website and SEO best practices? (Skills, Knowledge)
  • How long has “someone” been doing this work? Who else do they work with? (Authority, Credibility)
  • Will “someone” be there when software needs updating, or you have a problem and need help? (Trust, Dependability)
  • How does “someone’s” process work for getting your desired outcome for this work? (Confidence)

I did not recommend she actually say those things to the prospective client …. but it serves as a good exercise to help you answer these questions:

What sets you apart?
Why are you different?

Which is really another way of saying, Why should I pick you?

Although it’s frustrating to think we are competing against amateurs or even have to go through this, it can be used as a good exercise to further understand our positioning, our strengths, etc.


This post is part of my 30 Days of Clicking Publish