On Journaling

If you do any research on how to increase productivity or how to “win the morning”, you’ll no doubt come across the benefits of journaling. I journal myself — it has incredible benefits.

However I fell victim to an all-or-nothing mentality. For some reason I felt I had to journal at least once a day — the ideal being once in the morning and once at night. As someone with a busy schedule, it quickly becomes clear how that’s not always realistic.

Of course there’s the “you don’t have 5 minutes to spare?” argument. But a question like this requires a simplistic view of life. Sure, I could carve out 5 minutes. But often those 5 minutes are better spent on something else.

Taking that a step further … if you were to carve out 5, 10, 20 minutes for every productivity hack out there, you wouldn’t have any time left in the day for actual work or relationships.

In 2018 I’ve been working on my focus. And, as a consequence of focus, I’ve been working on ridding myself of that all-or-nothing mindset. Of the pursuit of clean perfection.

That’s taken form with my blogging. With my reading. With my work. With my relationships. It’s a reality that I couldn’t bring myself to think of in the past. But now that it is my reality — I’ve seen how freeing it is.

You don’t have to finish that book. Had enough of it? Put it down and pick up the next one. You don’t have to write the perfect blog post. Get your thoughts down and publish. You don’t have to journal everyday. When you do, you’ll find it’s great. And when you don’t — that’s okay too.

I love to journal but I now love to journal even more because it no longer feels like a chore. Something that I have to do or otherwise I haven’t “won the morning”. Now it’s something that I choose to do. Something that I enjoydoing. And you know what? My day can be great regardless of how I spent those 5 minutes. It’s a matter of how I spend the rest of it and my outlook on it all.

Ironically I started writing this blog post about journaling and how I’ve found it beneficial when I do it. Then it morphed into something completely different. And you know what? That’s perfectly fine.

This Question Will Immediately Improve A Company

Each Monday I have 1-on-1s with members of our team. We each have a list of topics to cover, discussing what we need to focus on and accomplish that week. There’s often a lot of crossover.

After that, I’ll dive into broader questions to better understand where their head is at. I’ll ask things like:

What are we too focused on?
What are we not focused enough on?
Are you getting enough direction from me? Too much or too little?
What’s one thing you’d like to change?
How can I better support you?

The questions vary from week-to-week. And there’s one I asked recently that’s proved to be incredibly useful.

Background: Our operational focus for 2018 is optimization. We’re working to streamline the process of how we do everything. How we serve customers. How we build product. How we communicate with each other… everything.

Aimed in this direction I asked the following question.

“What do you ask for or get asked for repeatedly?”

This question, and the ensuing conversation, has massive benefits. Let’s list them out.

1) Context.

Creating a strong communication architecture is about enabling people to share their context. It’s why, at Moved, we have weekly All-Hands meetings and monthly “State of the Move” meetings. In those I’m sharing my context as CEO — putting the “why” behind the “what”. This question accomplishes the same thing but in the opposite direction. It allows me to better understand the context that team member is working within.

2) Empathy.

Understanding their context is a prerequisite for empathy. I’m showing that I give a shit about what they’re doing and want to help with any problems they’re facing. This creates trust — followed by an open, honest conversation.

3) Identifying Blockers & Time-Wasters.

A blocker is something that stands in the way of someone getting their job done. They’re unable to complete a task without waiting on someone else. That “someone else” then has their own work interrupted because they need to unblock their teammate. If this same request comes in constantly it becomes an annoying time-waster.

Asking the above question will quickly identify the biggest blockers and time-wasters in the company. They won’t be difficult for the team to surface. But they can only be identified if the question is asked and the platform is provided.

4) Automate & Streamline.

Once identified, the blockers and time-wasters typically aren’t difficult to get rid of. Build a feature, create a process, train somebody on something new… the solutions are easy to see. And they have a compounding impact.

By breaking down the barriers and distractions, the team is able to be more efficient and effective in their roles. On top of that, it’ll be appreciated that the company listened and quickly made changes to empower them.

5) Autonomy & Mastery.

I’m a big believer in building a strong culture. I believe you create it by giving the team 1) a sense of purpose 2) autonomy and 3) mastery. Those two sentences are an incredibly simplistic view of what could be a book (or multiple) on culture. But, for the purpose of this post, let’s focus on #2 and #3.

By identifying, automating, and streamlining the things that the team repeatedly asks for or is asked for — a certain environment is created. An environment where they can work independently and get shit done. Where they can leave others to focus on their own work and get more shit done.

It makes everyone increasingly independent and also provides them the ability to master their work. To be specialized and go deep on what they do. It’s a positive for the organization and it’s a great feeling for the individual.

Dealing With Stress

Stress is something we all encounter. And it’s not talked about enough.

We’re forced to figure out how to handle this burden by ourselves. Some are proactive about it. Some deny it’s there. Others know it’s there but decide to ignore it.

You don’t have to be at a startup to experience stress. It pops up often in our personal lives and day-to-day interactions. How you deal with it is important. I’m far from perfect in that regard, but here are a few things I’ve found to be helpful.

1) Acknowledge It

This is something I’ve discovered through meditation. Recognizing when you’re feeling stressed or anxious is the first step to minimizing the impact it has on you.

It’s okay to feel stressed. It happens to everyone. When it starts to come over me, I’ll pause, breathe, and think, “okay, that’s stress”. I acknowledge it’s there and that it’s a normal feeling. Categorizing it as such will immediately make me feel better, emotionally and physically.

2) Keep Perspective

Okay, I’m stressed… now what? I find it helpful to put perspective on it. Is this the biggest problem in the world? It’s certainly significant in my world, but how does it compare to what else could be wrong? Better yet — what do I have to be thankful for? While I may be stressed about a problem happening now, there are plenty of positive things in my life that I have to be grateful for.

Looking at stress through that lens is helpful. It allows you to express gratitude for the things you might otherwise take for granted. Often stress is a result of a narrow perspective. Widening it helps a lot.

3) Reflect With Time & Space

Take a walk. Get fresh air. Go to the gym. Just get away and do something else. Bonus points for something physical. This helps me to think and achieve #1 and #2 above.

I find I need to create space between me and what’s causing me stress. That space is created through the time away from it, and by focusing my mind on something else entirely. It enables you to come back to the problem with a fresh outlook.

4) Take Responsibility

The blame game is easy to play — but it gets you nowhere. Regardless if this problem is your fault or not, use the time and space to think about what you could have done differently.

It’s not easy but, by operating from a place of “this is my fault”, I find that I’m more able to deal with the issue at hand. When things are out of your control, they’re more stressful. By taking responsibility you can change the conversation around the stress and give yourself the power to change it.

5) Move Forward

I use the above to make myself feel better, both emotionally and physically. But that doesn’t solve the problem or completely shed the stress. It does put me in a better state to address it, but it doesn’t do the job for me.

The problem still exists. The anxiety is still there. But now I’ve put more thought into it, I’ve had time to reflect, and I’m ready to face it head on. Running and hiding from problems accomplishes nothing. They might be scary but the only way to get passed them is to push ahead. Accept them for what they are and move forward.

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This is how I deal with stress but I’m always looking for new ways to tackle it. How do you deal with stress?

The First Step For A Startup

I was recently answering the question, “What is the best first step for a startup?”

My answer is simple. The best first step for a startup is to identify your customer’s problem. That’s it.

To do this you’ll need to talk to customers. A lot of them. You should be your own customer.

An intimate understanding of the customer’s problem is a prerequisite to actually solving it. Seems obvious but you’d be surprised how often people start elsewhere (I was one of them!).

Talking to customers provides incredible insight. You’ll understand who they are. What problems they have. How they hack a solution today. You’ll emerge from those conversations with a hypothesis on how you can solve their problem(s) and provide them value. Test that hypothesis, learn, and iterate.

If you aren’t solving the customer’s problem then you aren’t building something people value. Something they’ll love and use. Without that, you don’t have much of a business.

The concept is simple. The execution is hard.

Keeping Perspective

Yesterday was the AFC Championship and your’s truly is a big fan of the Jacksonville Jaguars. I won’t get into the details of the game because that would become a post of it’s own and the loss is still raw. Luckily work has been a welcomed distraction today and I’ve had a great, productive day.

It’s been a somber day for Jaguars fans, no doubt. Still, it was a season to remember for a franchise that’s had a rough 10 years. While I believe they should be in the Super Bowl, sometimes things just don’t work out as you’d like them. Such is life.

What’s funny is how much a sports game can impact your emotions. In the grand scheme of things, the game means very little. But sports have an incredible way of bringing people together. I was lucky enough to watch the game with a great group of people and had a Sunday afternoon I won’t soon forget. While the loss sucks, it’s helpful to keep that perspective.

Also — watch out for the Jaguars next year. They’ll be back 😏.

New Opportunities

Early stage startups are busy. It’s not difficult to fill your schedule each day. I’ve talked on this blog before about saying “no” to some of those things and clearing your schedule to focus. Clearing space to think and create.

But this doesn’t mean you should completely cut yourself off. Thinking and brainstorming alone can only get you so far. You need other inputs. You need to read things. You need to meet with new people. You need to learn about other businesses and emerging technologies.

Doing this opens you and your business up to new opportunities. Keeping pace with competitors isn’t enough. You need to innovate. You need to create new efficiencies. You need to find ways to provide value to customers.

You do that by taking yourself out of the industry and out of the assumptions of the incumbents. Learn from the outside and innovate on the inside. Above all, put your customers first and provide them with a great experience.

Cut The Fluff

Last year I signed up for Audible. I listen during my commute and, as a result, have dramatically increased the number of books I consume.

The majority of what I read is non-fiction. One theme across many (not all) of these books is that they could be much shorter. There’s one or two strong arguments and the rest of the book is filled with stories of how that argument was applied by somebody.

Examples are useful up to a point. After that, it’s fluff. Extra filler chapters to make the book longer and pricier. I don’t need the fluff. Give me the good stuff. Cut the fluff. It’s useless and repetitive.

Now as I start to see signs of this I’ll fast forward a bit and eventually drop the book if I feel I’ve gotten the point. That’s what makes services like Blinkist popular.

In general I’m not a fan of fluff. I try not to consume it or produce it. Writing without fluff is stronger. A product without fluff is more effective. Life without fluff is just… better.

Cut what doesn’t matter. Keep what does.

The Power of Deadlines

I learned the power of deadlines when I was beginning my career as a product manager. A core responsibility of a PM is to ship product. It seems obvious but it’s easier said than done.

Shipping earlier means getting value to your customers and learning faster. Beyond that, setting a release date provides a deadline for the team. This deadline acts as a forcing function. The constraint of time forces you to focus on the task at hand, rank what’s most important, and cut what’s not.

I’m seeing this now with a big project we’re working on at Moved. Not only are we shipping new product but we’re making big changes to the way we operate internally. The project involves everyone in the company, making communication and coordination essential. Each person has their role and we’re all focused on getting to the finish line. Even after the “finish line” (launch) there’s a lot of work to make sure all goes well into the future.

Deadlines can be stressful but they can also create moments of magic. Seeing everyone rally and execute in crunch time is a thing of beauty.

There’s more work to do but it’s useful to take a step back and appreciate the big moments as they’re happening. Thanks to this blog for allowing me a few minutes to do that. Now back to work.

Focus, Focus, Focus

Last week I tweeted this.

My 2018 theme is Focus

— Adam Pittenger (@apitt24) January 5, 2018

A friend asked me to elaborate on this. Why is that the theme? What does this mean for me?

My Answer

To me, focus is more of a mindset than a verb. It’s a way of operating that guides your actions and decisions.

It’s a mindset of prioritization. Setting a goal and creating a prioritized list of actions that will cause you to achieve it.

It’s being relentless in pursuit of that goal. Delegating more and understanding how to best use the resources you have.

It’s force-ranking everything. Eliminating anything that distracts from achieving the end goal.

What This Means For Me

This means changing how I spend my time. There’s a lot of calls and meetings I would have said “yes” to that I’ll now say “no” to. It means being protective of my calendar, rather than at the mercy of other people’s schedules. It means structuring my day in a way that optimizes my time and moves the company closer to our goal.

Nothing great in life gets accomplished without focus. So focus.

Structuring A Day

I didn’t publish a blog post yesterday. An urgent request upended my morning. It took me until 2:30pm to finish before doing any other work (or eating).

This is not the way I like to start my day. Unfortunately, it happens in a startup. It’s the nature of the beast. On all other days I have a specific day structure I like to stick to.

The optimal structure of one’s day depends upon who that person is and how they operate. I’ve designed mine to take advantage of the creative thoughts I have in the morning. I then batch my meetings, phone calls, and “manager time” in the afternoon.

If you’re not familiar with the idea of a maker’s schedule vs a manager’s schedule, I recommend this post (and/or this one). If those are too long, here’s a great video that I showed our team this morning when discussing this very topic.

The Structure of My Day

I like my mornings to be for making. I write. I work on product. I think and problem-solve. I try not to check email until I’ve completed at least one big “maker to do”. I’m not always successful in that but I’m getting better.

Around noon I switch from maker to manager. The rest of my day breaks up into 30 and 60 minute blocks of calls, meetings, and administrative work.

Each week I audit how I spent my time and adjust from there, optimizing for the highest yield activities. I break those activities into inputs and outputs.

My highest yield inputs = talking to people (to gather information), reading, and research.

My highest yield outputs = talking to people (to deliver information), writing, and product work.

I work to structure my day and my role to optimize for these as much as possible. It’s an exercise of continual iteration and improvement. Time is a finite resource. It’s the most precious thing we have. How are you spending your’s?

The NFL Playoffs

From time to time I’ll write about sports in here, especially when it’s top-of-mind like it is today.

The NFL Playoffs are an awesome time of year. While the series format (e.g. NBA) has merit, the “win or go home” nature of the NFL Playoffs raises the stakes. It makes each game that much more important.

Today my team, the Jacksonville Jaguars (I was born in JAX) are in the playoffs for the first time since 2007. They’re hosting a playoff game in Jacksonville for the first time since 1999. Needless to say… I’m excited.

Content Begets More Content

On January 1, 2018 I started writing this blog with a specific goal in mind. The goal is to “write everyday and/or publish 300 posts”.

I phrased the goal in this way because “write everyday” isn’t a well-structured goal. While that is what I’m doing and it’s a habit I’m working to form, it doesn’t set me up for success. If, for whatever reason, I have to miss a day and can’t publish a post — I’ve failed and missed that goal for the year.

By saying “and/or publish 300 posts”, I give myself room to have days where life gets in the way. And should I miss that day, that’s okay. I’m still on pace for the 300 mark and the daily ritual of writing will get me there (and likely above it).

Today is the sixth day of this ritual and I’ve already found an interesting side effect. The more I write and publish, the more I have ideas for other things to write and publish.

I wrote in the initial post (of writing)…

“It allows me to offload the top-of-mind thoughts and make room for the interesting ones hiding below the surface.”

Not only has this proven true, but it feels phenomenal. I’m more energized and stimulated mentally. It’s having the desired effect, which only motivates me to keep it up.

Do You Shovel or Do You Wait?

After yesterday’s snow day, I noticed something during my commute home. Some businesses had their sidewalk shoveled, while others didn’t. A gesture like this, although minor, tells you a lot about a business. About how they operate and treat their customers.

In the world I live in (software startups), the snow is harder to see. But have no doubt — every business has snow at their storefront. Issues arise and impact the customer’s experience.

When your customers run into an issue that wasn’t cause by you (the business), how do you respond? Do you go out of your way to make it right? To clear a path and make sure their experience is positive? Or do you throw up your hands and force the customer to deal with it?

Hospitality is hard work. Putting customers first isn’t always easy. But it is the right path. Customers notice when businesses go out of their way to provide a great experience. And they express gratitude for that through loyalty and referrals.

Don’t wait for the sun to melt the snow. Shovel, shovel, shovel.

Snow Day

Here’s a glimpse of the Northeast today.

weather.com

And my walk to work.

Snow Day commute

4 Likes, 2 Comments - Adam Pittenger (@apitt24) on Instagram: "Snow Day commute"

As a kid I loved snow days. It was an anomaly. A day that interrupted the regular routine of school. A day to go play outside with friends. A day with a hint of chaos as the “adults” always seemed to be a bit panicked and unsure of what to do.

To me it was all a welcomed change. No class was great. Playing in the snow was fun. Warming up inside with soup and TV was (and still is) one of my favorite feelings.

Now, as an adult, snow days are less fun. It’s not the precipitation I mind. Rather, business closures and transportation issues can make life more difficult and potentially dangerous.

With that, to my friends here in Northeast… stay safe, stay warm, and enjoy your snow day.

Getting to sleep

I’ve always had issues getting to sleep. Without a doubt — I’m a night owl. When it’s time to go to bed, I struggle to shut my mind down and get the rest I know I need.

In the past I’ve always had the TV on and/or been messing around on my phone. Clearly not effective. I’ve tried a number of tactics and hacks throughout the years to fix this. The only one that seems to work for me is reading.

Everyday I read on my commute via Audible. But that’s not effective at night because, if I fall asleep, I completely lose my place in the book. A physical copy is the way to go.

The next issue to get past is the light. My fiancé goes to bed earlier than I do. She puts her head on the pillow and is out. It’s almost as if she has an “OFF” switch… a true gift. I don’t want to put on the bright lights because 1) it may wake her and 2) I don’t want to have to get up to shut them off as I’m falling asleep.

So I’m going to try the Phillips Hue lightbulbs. The ability to dim is a plus because it won’t wake my fiancé and the different hues you can set will allow me to “set the stage” for sleep. Finally, when I’m primed to drift away into dreamland, I can turn them off completely via my phone.

At least that’s the plan anyway… I’ll let you know how it goes.

Investor Updates

Yesterday I wrote a company update to all of our investors. This is something I send each month on the 1st. It outlines where the company is at, what we’ve accomplished, what we’re focused on, and what we need.

I’ve come to appreciate these updates more with time. They serve a number of useful purposes.

1) Reflection.

Looking back at the previous month (or year) allows me to gain perspective about all that we accomplished. It’s easy to get lost in the weeds and continually push towards the next goal. While that’s not necessarily a bad mindset, it’s important to look back and celebrate wins. Not just because it makes you and your teammates feel warm and fuzzy inside (it does), but because there’s valuable learnings in that reflection exercise.

Each month, while setting goals, our team reviews that last 30 days. What did we do well? What didn’t we do well? We take those learnings and create specific actions that reinforce the positive and embed those learnings into our company.

2) External Communication.

Keeping investors updated is a good thing. First, it can save you redundant check-ins because curious investors know they’ll be getting the email soon anyway. Second, it establishes an open line of communication. It’s an email overview of where the company is at (often with an “Ask” in it), not only providing an update, but also creating a thread that they can reply on top of — if they can help with something or have a question. It also makes investor meetings easier because nobody is in the dark about what’s happening with the company. There’s no multi-month lapse where they’re not sure what’s been going on.

Finally, if your updates are thorough and forthcoming, they can serve as an excellent sales tool with new investors. You can forward last month’s update to an investor who is interested in the company. Not only is it a great overview but you can illustrate what it’s like to work with you as a founder and how you’ll communicate once they’re on the cap table.

3) Internal Communication.

This takes form in a couple ways. When creating the email, it’s necessary to get updates from colleagues throughout the company. It’s an opportunity to dig into the numbers, learn more about projects in progress, and hear what’s working and what’s not.

Perhaps even more important is sharing context. In my job as CEO, I have a more holistic view of our company than anyone else. I’m a bit of a curator in that way. I receive inputs from everywhere (customers, sales, marketing, product, operations, investors, other founders, lawyers, research, etc.) and my output is synthesizing and prioritizing those to create a direction for the company. It’s crucial that I share my context with our team internally. Providing them not just with the “what” but also with the “why”.

This takes shape via our weekly all-hands meeting but also through these investor updates. Each employee at our company is on the distribution list so they too can see the holistic picture and understand how our progress and status is being communicated to investors.

Perhaps I’ll share the template I use for our investor updates in a future post, if people find it useful.

New Year, New Blog

I imagine I’m not the only one starting a blog today. It’s January 1st. A day many kickoff new habits, routines, diets, etc.

I’ve also blogged before. I’ve written a number of posts for different publications over the last few years. So what’s different now? Why am I doing this?

1) To flex the muscle.

My main objective is to write more. I love to write. It’s cathartic for me. It allows me to offload the top-of-mind thoughts and make room for the interesting ones hiding below the surface. It’s also an exercise for me to better understand myself and make sense of all the information I take in on a daily basis.

2) Increasing frequency.

To achieve the above, I need to make this a habit. Something I do everyday. And to do that, I need to change my style.

3) A new style.

In the past I’ve spent way too much time editing and revising posts before publishing them. No more of that. I’m pushing outside my comfort zone and spitting in the face of the need for perfectionism. No individual or blog post is perfect. Accept that and publish.

What this also means is that my posts will vary in length. Some will be a paragraph or two. Others will be 1,000+ words like most of my previous posts. It will depend on the day, the subject, and my schedule. I’m not committing to a certain style — I’m committing to the frequency. Making the exercise a habit and forcing myself to hit ‘Publish’.

So, no, this blog isn’t for you. It’s for me. It’s to get myself in the practice of writing everyday and ridding myself of the debilitating search for perfectionism. And if, along the way, some of the posts prove to be valuable to others… then great. That’s my new definition of perfect.

How A Properly Set Goal Can Change Your Life

The Formula I Use to Be Happier and Achieve More

I want to be successful.

Who doesn’t? Ostensibly everyone is working to be successful. Which begs the question… how is success achieved?

This question has dominated my headspace throughout my life and career. Eventually I realized — you can’t start answering the ‘how’ without first answering the ‘what’.

In retrospect, the chronology is obvious. It’s frustrating to think how long the obvious eluded me. I knew, inherently, I wanted to be successful. I just never took the time to define what “success” meant to me.

Wanting success is great but “I want to be successful” is not a goal. It’s an ambiguous phrase with different meaning to different people.

Without defining success, how can you understand what it looks like? How can you tell when you’re making progress? How can you ever be successful? You can’t.

Following this realization, I created a process for myself. One designed to push me in the right direction and, if followed, would force me to “be successful”. Thus far, the results have been astounding. I’ve learned even more than expected.

This process now influences everything I do, both personally and professionally. It’s helped me to lose weight, accomplish business goals, and become a happier, more positive person.

The process is five steps — they are:

1. Define Success

If we’re being literal, the dictionary definition of ‘success’ is: “accomplishing an aim or purpose”.

Okay, so what is my aim or purpose? What is it that I’m trying to accomplish? The answers to these questions define my vision of success.

Be clear — this vision isn’t always easy to define. It may be top-of-mind or it may require serious introspection to nail down. A good practice is to identify other people who you would qualify as “successful.”

What about them is successful? What aspects of their lives do you wish to achieve in your’s? Any successful person you speak to or study will tell you they had people they were emulating and chasing at the start.

The vision of success can be anything. A raise or promotion. Buying a house. Working one less day a week. Spending a certain amount of time with friends and family. Anything.

Two Rules

1) Don’t be ambiguous. “I want to have a popular podcast” or “I want to be a successful investor” are not good enough. You need to define what ‘popular’ and ‘successful’ mean. Otherwise they are unattainable. Be as specific as possible.
2) Create inevitability. Don’t express the vision as “I want to”, express it as “I’m going to”. Definition without action is meaningless. A decision must be made. Decide not what you WANT but, instead, what you’ll DO. Definition becomes decision when action is taken.

2. Set Goals

Once the vision is defined, it becomes clear what “success” means and what it looks like. The next step is figuring out how to get there.

I start by working backwards. I keep working backwards until I have a concrete next step. That next step is my first goal.

Ask The Following: What are the prerequisites (milestones or credentials) for this vision? How have others accomplished it (or something similar) before? Can I achieve the same result in a more efficient way?

Let’s use an example and say my vision of success is: “I’m going to have a podcast with one million downloads”. Working backwards from that, the first thing I need is… a podcast. And if I want a podcast, I’ll need recording equipment and something to talk about. And working backwards once more — I’ll need to save up money for the equipment and brainstorm potential podcast topics.

At this point I can’t work backwards any further. I’ve peeled back enough layers where I now have two things I can take action on immediately. These are my goals. By accomplishing these, I’m making real progress and moving towards my vision.

Taking this a step further — once I’ve saved up money and figured out what I want to cover, I’ll have my equipment and my topic. Then I’ll set new goals. For example, recording the first season of the podcast. And after I do that… I’ll have my podcast. I’ll keep iterating until my vision of success is realized.

This, of course, is an oversimplification. But it illustrates how you can work backwards from the vision and set the appropriate goals.

3. Create Habits

Goals aren’t accomplished on their own. Identifying what needs to get done doesn’t mean it actually gets done. Goals are only accomplished by taking consistent action. Let’s continue with our podcast example...

If I need to save up for equipment, then I’ll make regular deposits into my “podcast fund”. Or I’ll get a loan. Or ask for a deferred payment plan. I’ll take action relentlessly until the goal is complete.

Now I have the equipment and my next goal is to record an 8-episode season within a month. For this, I’ll schedule time each week to record 2 episodes. It must become a habit. I’ll create rewards for succeeding and consequences for failing, to incentivize myself. With my new habit in place, I’ll have an 8-episode season by the end of the month.

Again, the example is basic but the concept can be applied to any goal. Define your vision of success. Set goals that will cause you to realize this vision. Establish systems and behaviors that make achieving those goals an inevitability. Next…

4. Track & Measure

This step is crucial for a couple reasons. First, it allows you to see how you’re progressing, what you’re learning, and if you need to correct the course you’re on (see #5).

More importantly — it informs your happiness and motivation. The truth is, many people feel unfulfilled because they don’t define and track their goals. I was one of these people for a long time.

Without defining success and tracking my goals, there was no way for me to see if I was actually making progress. By not seeing or feeling progress, I felt stagnant. Like I was running in place. And that’s a horrible feeling.

With clearly defined goals, I know exactly what success looks like. More than that, I can see how I’m progressing towards my goals. If I see positive gains, I’m happy. I know my goals are achievable and, better yet, they’re in sight. I just have to keep going. Keep pushing.

That’s where motivation kicks in. Seeing this progress, being happy and confident, and knowing my goals are within reach… these all push me to be persistent and take action.

Conversely, if I’m not tracking my progress, I’m in a state of limbo where I’m unsure sure what my hard work and long hours are resulting in. Is this actually furthering my goals? Am I doing the right things? Do I need to make a change?

The only way to answer these questions is to track and measure. It keeps you sane and motivated with the knowledge that you’re moving in the right direction and on track to realize your vision.

And that knowledge is directly correlated to your feelings of happiness and self-worth. The more control you feel over your destiny, the more confidence you’ll have and the happier you’ll be. And that, by itself, is reason enough to track and measure.

5. Review & Recalibrate

While going through the above, I’ve found it’s crucial to regularly take time to review the vision, the goals, and the habits.

This review process should not exclusively be completed at the end, but also along the way. Tracking and measuring organically forces this. As you go, it may become clear that a change needs to be made.

When reviewing, take time to celebrate success, analyze failure, and learn from both. If successful, was it the desired outcome? Was it what you expected? Based on everything you’ve learned, what’s next? How has the definition of “success” changed?

I’ve learned an incredible amount through this process. Through pushing myself to accomplish goals. The next step is to take those learnings and reset. Start again from #1. Think about the new definition of success and how it can be achieved.

A Shift In Mindset

You may think, “this sounds like a lot of work”. And I won’t deny that it does take time and effort. But if you aren’t deliberate about the things you want in life, then the things you want will elude you.

This entire process is aimed at changing your mindset and the context you work within. Once I did this, everything changed for me.

If you define success, map goals to that definition, and create habits that force action — you will succeed. As a result, your vision of success will always be top-of-mind.

Everything you do is geared towards being successful. Rather than sitting on the sidelines of a game that’s undefined… put yourself in a game where you determine what it takes to win.

This is a shift in mindset that tips the scales. The shift of being on the sidelines to owning the game. Of making decisions and taking action, rather than overanalyzing situations. Of treating life as something you make happen, rather than something that happens to you.

All you need is yourself. So go — make it happen.

2 Years Ago I Quit My 6-Figure Job To Start A Company: A Letter To Myself Then

It’s been 295 days since my last blog post.

The reason for the gap? I’ve been working.

There’s much beneath the surface of that simple headline. I’ve learned a lot in that time. And as I reflect on those learnings, I think about what advice I’d give to myself back when I started.

[TLDR: If starting a company, make sure 1) you know what you’re getting into 2) you understand your customers and the space and 3) you’ve asked yourself ‘why’. Feel free to jump to any section specifically; I know this is long.]

Rewind: Feb 2015
After entering Startup Land — I went through an acquisition, worked at a big company, and landed an offer at a startup paying me almost triple what I made just two years prior.

It was a whirlwind journey that left me infatuated with this new world; one with a never-ending list of possibilities and things to learn. I was intoxicated by the process of building something from nothing. And became convinced I needed to start my own company.

My conviction quickly turned to obsession. I had to escape my day job and make this my reality. So I took the leap. I quit my well-paid position for the wonderful compensation of $0 per year — but the career I longed for.

Fast Forward: Today
The last two years have revealed how flawed my logic was. While I have plenty of work and learnings ahead of me, if I could talk to myself two years ago, the below would be my advice.

This advice should not be construed as gospel — my views and knowledge on this journey continue to evolve. It is my hope in writing this, that the lessons learned can reach, and be helpful to, an aspiring entrepreneur who may be in a similar headspace to that of mine two years ago.

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Dear Me,

You’re young. And stupid. I come from the future — so let me school you, fool. Don’t interrupt. Just pay attention and take it to heart. You need to think about a few things…

1. The Decision To Start

I’ve heard you say, “I want to start my own company”. And I get it, I do. But let me tell you — this is extremely misguided thinking.

This thinking is derived from the romanticism surrounding startups and entrepreneurship. With success stories being glorified in movies, pop culture, and daily TechCrunch articles.

Newsflash: startups are fucking hard. Those massive success stories, while attainable, are nonetheless anomalies. Read about the power law of venture capital. Even if you go into it knowing it’s hard… I promise you, it’s harder than that.

Don’t take this pursuit lightly. If you intend to be successful (you do), you’ll need to dedicate the next 5–10 years to this single mission. Considering the human lifespan and the finite resource that is time… this is a significant investment.

You’ll need to allocate the majority of your time and, more importantly, mental energy towards this one goal. You’ll need to sacrifice money, relationships, and opportunities in an effort to will your vision into a reality.

And even after all of that… the odds still say you will fail. It’s a daunting proposition. But the brutal, honest truth you must recognize.

2. Founder/Market Fit

As a founder, you need to have an incredible passion and understanding of the market you’re in and the problem you’re solving. This dynamic, referred to as “Founder/Market Fit”, is the single most important question to ask before starting.

Again, this is an idea you’ll need to pursue for the next 5–10 years (the average acquisition is 7+ years, the average IPO is over 8). This is a market you’ll have to dedicate prime years of your life to be obsessed with.

The Takeaway: You must truly give a shit about what you’re doing. Many shits, really.

You need to care deeply about making your vision a reality. About helping the customer you’re serving and improving the industry you’re in. About the company you’re building and the people who join you for the ride.

Don’t start a company because you “want to”. Or because you “think you should”. Or because you think it will “give you freedom and flexibility” (lol).

Don’t start a company just to start a company.

Start a company because there is a problem you understand intimately and you can’t sit around anymore without solving it.

And then, still don’t start the company. Start solving the problem.

Often people fall victim to confirmation bias. They spin their thoughts and the information around them, convincing themselves that starting a company is what they need to do. They tell themselves they love XYZ industry and are obsessed with fixing it. When really they just want to get out of a job they hate or find some work/life balance.

This “grass-is-greener” point of view is easy to fall into. But you need to think objectively at what you’re trying to do and why.

Anyone can start a company. But starting a business you’re not passionate about is setting yourself up for failure. Because…

1. You’ll be thinking through and dealing with the ins-and-outs of this business every day, every minute — for years to come. If you hate it, you’ll be miserable and it will always feel like “work”.
2. If you’re not passionate about it, that means that someone else out there, who is passionate about it, is better positioned to solve the problem. Play to your strengths, favor your interests, and give yourself the best chance to succeed.

Mostly, ask yourself “why?”. Why do you want to start this company? And be brutally honest with that answer. This sort of introspection can open up thoughts and ideas you didn’t know existed before.

If you decide it’s worth pursuing, your next step should be conducting extensive research to understand the industry and the solutions available. And more importantly…

3. Talk To Customers!

I know you’re a product manager and you have great wireframes and the designs look beautiful and… no. Stop. If you’re contemplating starting a company or building a product, this is the ONLY thing you should be focused on.

Talking to customers will be highest yield activity you can spend your time on. At any stage, talking to your customers provides incredible insight, but it’s markedly important when you’re just getting started. The learnings and takeaways from these conversations will guide you on where to start and where to focus your attention.

You need to understand your customers intimately. Ideally, you should be one. Understand who they are. What problems they have. How they solve them today. And, with a big enough sample size, how you can help them solve these problems in a better, more efficient way.

After doing this you’ll wonder how you ever thought about starting a company without talking to customers first.

And lucky for you, you don’t have to quit your job or invest any money to do this. Just talk people. Call them. Write an email. Take them out for coffee or drinks. Talk to as many as you can. Be relentless — like the future of your company depends on it. It does.

Related Note 1: You may want to create a blog, instead of building software, as your “MVP”. This could be a powerful way to dive deep on a topic, understand your customers, and build an initial audience.

Related Note 2: Here is a great list of user interview questions you can use.

4. Have A Co-Founder

I’m not saying solo founders can’t be successful but it does carry unique challenges. While you won’t be subject to co-founder infighting, with a second or third founder you can: get 2–3x the amount of work done (notably in the early stage where everything is manual), apply different perspectives and skill-sets to the same problem, and have a more appealing pitch to investors (some avoid solo founders).

Perhaps the biggest reason is that the emotional ups and downs of the job can be draining. Founder depression is a real thing — something I’ve experienced myself. It’s helpful to have someone in the trenches with you, who understands the details of what’s happening. Someone who can sympathize, support, and work with you to solve problems.

5. Have A Support Network

Co-founder or not, you must have a solid support network around you. This network can take different forms and provide different types of utility. Your personal network helps take care of the emotional layer — the baseline for operating each day. Surround yourself with friends and family who cheer you on, understand the stresses and demands of your job, and can be there to talk when called upon.

A professional network is equally important. This network serves to give you honest feedback. To keep you grounded and provide educated, actionable advice. They can help you brainstorm and solve problems. They can make introductions to people valuable to your business, and help grow the network over time.

Note: Don’t forget to give back to these networks. As a rule, try to give more than you receive.

6. Thick Skin

The support networks help but only you experience what it’s like to be in your shoes every day. So you’ll need to have (or develop) thick skin.

Life as a startup founder is riddled with more downs than ups. More “no” than “yes”. And more caffeine than sleep. I can’t say it’s the healthiest lifestyle choice. Early-stage startups demand a lot of time and sometimes you won’t see immediate results.

Understand that things are never as amazing or as horrible as they seem in the moment. Keep a level head and remain focused on your mission. Be open to feedback but persist on the things you know to be true. Don’t let one meeting get you down, or another convince you that you’ve made it. Take the hits, keep pushing, and hustle on.

7. Understand Investors

Always seek to understand your audience, no matter what you’re doing. Raising money for your business is no different. Understanding how venture capital works is imperative to raising that money. While not as important as understanding your customers and building something they love, if you don’t understand the motivations and incentives driving the person across the table, you aren’t setting yourself up for success.

8. Core Values

Establishing your core values at an early stage is one of the more valuable things you can do as a founder (after research/talking to customers).

It doesn’t matter how small you are. 1–2 person companies should do this. It may seem unintuitive at that size, but trust me (I’m from the future)… take the time to define your mission and core values. The good news is — they should already be inherent to who you are and what you do. You just need to talk it out and write them down.

Not establishing your mission and core values is the equivalent of sailing in a vast, open ocean without a compass.

These will inform everything you do moving forward. Hiring. Product. Strategy. Prioritization. Metrics. Goals you set. Performance reviews…. it’s the baseline for gauging everything.

The culmination of all of those decisions is what creates your culture. And culture is created whether you craft it or not. So you might as well be deliberate about what you want it to be. There’s nothing more important about your company than the people. And culture is what determines the type of people you hire, the talented people you retain, and the success of the product/service you all create. You cannot ignore this.

9. Taking Care of You

We touched on your emotional wellbeing within the context of your business — but there’s more to it. A few points here…

Physical

Seemingly obvious, this portion of personal health is often the first to suffer. For me, I deprioritized my physical health because there was nobody holding me accountable. For everything else in my life there were people who counted on me. My health was my problem, and when days got busy (they always do), I would skip. It wasn’t until I reframed this in my mind that I started making my health a priority.

You need to be at your best for your immediate network. You need to support your family, friends, and colleagues to the best of your ability. And part of that is making sure you’re healthy, focused, and capable of being there when needed.

Reading

Think of it this way… there is an opportunity cost to not actively reading.

New ideas are formed when your brain connects different thoughts, concepts, or experiences together in your mind. Applying a theory, story, or solution that you read about, to a problem in your life… that’s where creativity and innovation live.

Reading is the avenue to get you there. If you can only pull from your existing arsenal of experiences, vocabulary, and ideas — then you significantly limit your ability to solve problems and think creatively. This also applies to organizations. Valuing and recruiting for diverse perspectives makes your team better equipped to solve problems.

Writing

If reading gives you the ammo to work with, and your brain is the weapon — then writing is the trigger. All those creative thoughts and ideas are effectively useless if you don’t get them out.

On top of that, writing has this wonderful compounding effect. It makes room for more creativity. As you begin writing, you’ll find that new ideas start coming to the surface. Getting those top-level thoughts out clears way for a whole new layer of ideas to rise up.

Make sure you write every day (morning is typically best). Challenge your brain with interesting questions and scenarios. And take time to revisit and review ideas. Reading your own thoughts from a different time and headspace can often be the same as reading someone else’s prose. It can help to place you, mentally, back in a different space.

10. Keep Learning

Understanding that you don’t know shit is one of the most empowering mindsets you can take. That’s not to say you shouldn’t be confident, but there’s an important difference between confidence and arrogance. Putting on a false sense of expertise is actually detrimental.

Fuck “fake it til you make it”. Know what you don’t know and seek to keep learning and improving. This will give you all the confidence you need because you won’t be afraid to say you don’t know something. To ask for help. To learn and tackle new challenges in innovative ways. That’s how the best get better, solve problems, and succeed.

Keep on pushing,
You +2 years

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This letter is by no means a comprehensive guide on how to start a company. It’s also targeted at a company’s super early, origin stage. Each of the above could be it’s own post and plenty of lessons simply didn’t make the cut.

The point of this isn’t to delay the action. As a startup founder, all you should be doing is taking action. But those early actions could be this diligence process — helping you understand what you’re signing up for and preparing you for success.

At a certain point there are diminishing returns — where that extra book, blog post, or phone call isn’t going to make the difference. At that point, the only way to learn more is to dive in and keep learning as you go. Entrepreneurship is like a pool in that way. Just make sure you’re not oblivious to the lessons above and you’re making this massive life decision for the right reasons.

After that… push forward and hustle to make your vision a reality. It’s on you to make it happen.

This 2-Step Process Will 10x Your Daily Performance

How To Plan Your Day At Night

Imagine you’re an actor.

It’s opening night of a Broadway play and you’re the star. You’re backstage thinking of all the praise and accolades you’ll get. The illustrious career that lies ahead.

You hear the stage manager yell, “Places in 5!”. And then you realize…

Shit — I never even looked at the script!

This is the equivalent of not planning your day at night.

Every day you have on this Earth is an opportunity. An opportunity to make something happen. Precious time that shouldn’t be wasted.

If you wait until the morning to plan your day, three things happen:

1. You’re asking for stress and anxiety.
2. You won’t be as productive as you could be.
3. You won’t be as effective as you could be.

Let’s break these down…

1. Stress & Anxiety

Take our actor scenario. The curtains go up, the lights shine on you, and…now what?

You’re in a panic. You’re not sure what to say, what to do, or where to go next. In the best case scenario you’re improvising and making up something decent as you go.

Another good example is a football player not knowing the play before the ball is hiked. It’s a recipe for disaster.

2. Less Productive

If you’re stressed and anxious, you aren’t fully present. You aren’t able to focus clearly on the task at hand. Your mind wanders, thinking about what you need to do next and wondering if you’re missing anything.

This mindset makes it difficult to a) get things done and b) handle unforeseen challenges as they arise. You’re forced to adapt, prioritize, and schedule on the fly.

If you haven’t already set priorities for yourself (see #2 here) then it’s likely you won’t get important things done that day. Emails will bury you, meetings will derail you, and by the time you finally getting a handle on things, the day is almost over.

3. Less Effective

Considering the points above, the quality of your work will obviously suffer. You’ll feel rushed, discombobulated, and unable to provide your complete attention to your work.

Perhaps a more important point here is decision fatigue. By not planning and visualizing your day, you are forcing yourself to constantly make decisions throughout. Big or small, it doesn’t matter. As the day goes on this wears on you.

Mentally exhausted at the end of each day? That’s decision fatigue at work.

Although subtle when isolated, the impact of continually using your brain’s processing power for small decisions quickly adds up over the course of a day. Not planning ahead tremendously increases the number of these decisions you have to make.

You’re so tired from the mental energy exerted to go through that day that you say, “eh, I’ll deal with this tomorrow” and the cycle repeats itself.

Here’s What To Do

It’s clear not planning your day has negative impacts. Luckily this bad habit is an easy one to break. It requires two steps and less than 20 minutes a day.Here’s how…

STEP 1: Plan Your Day At Night.

Take 10–15 minutes and do the following:

1. Look at today’s calendar. Take stock of what you did and note any needed follow ups for tomorrow.
2. Look at tomorrow’s calendar. See what calls or meetings you already have on there.
3. Look at your To-Do list. Refer to the “Post-It System” (#2 here) if you need help on this. See what your top three priorities are and block out time for them on your calendar.

I can’t tell you how important this is. One great benefit is a feeling of content as you finish your day. Reflecting on things you did and noting things that still need to be done provides a sense of closure. It becomes a ritual of sorts, signaling the day’s end.

A second benefit is that you feel more on top of your life and the important things you need to get done. Everything feels in order. You’re in control. Sure, unexpected challenges may pop up (they will) derailing your priorities — but you’ll be in a better position to handle and quickly adapt to it.

STEP 2: Stop. Breathe. Visualize.

Once you’ve planned out tomorrow, take a few minutes to visualize what your day will be like. Visualization is an incredibly powerful technique that is used by the highest performing people in the world. Try it.

Think about yourself waking up. About what your morning looks like. A morning routine is a great thing to have (a little more on mine, #3 here).

See yourself walking into that office, taking that call, crushing that meeting. Actually watch it happen as if it’s a show on Netflix.

Go through the entire day. Take a breath. And sign off.

You’ll go to bed calmer and wake up calmer. You’ll feel more confident and prepared as you start your day. And when that meeting comes up — why be nervous when you’ve already seen yourself crush it? It’s just the next thing on the list. An inevitability.

The day will be less stressful and you, as a result, will be more productive and effective. Getting the shit you need done — and well.

So go. Give it a try. Plan your day at night and report back. See what sort of impact it has on your life.