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.

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?

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.

How I Reduced Stress, Increased Productivity, and Made Myself Happy Again

“His palms are sweaty, knees weak, arms are heavy.
There’s vomit on his sweater already, mom’s spaghetti.
He’s nervous, but on the surface he looks calm and ready…”
-Eminem, “Lose Yourself”

This was me.

No, I’m not Eminem. And no, I’m not walking around with spaghetti on my sweater. I don’t really even wear sweaters.

But I was dealing with constant feelings of stress and anxiety. Starting a company is fucking hard. There’s no manual for first-time founders.

On the surface I looked and acted as normal as I could. But truthfully, I was overwhelmed.

I was a swelling balloon that never popped. But rather I began to deflate gradually. You don’t recognize it at first. After a while though, you notice something isn’t right.

Me^

It was the way I worked that enabled the worst in my obsession with productivity. An OCD-like infatuation that resulted only in self-sabotage.

It had created an unhappy person obsessed with all of the wrong things about work. An unsustainable modus operandi.

And so I needed a fresh start. I began to embark on a complete reinvention of my operating model. A full reset of the mind and the creation of a new system for doing things.

Fast forward to now…

I’ve gotten more work done this week (it’s Tuesday at 4:30pm) than I would have previously in a 7-day week.

And — I’m not stressed, or anxious, or even close to burned out.

I’m happy. I’m energized. I’m fucking excited.

Here’s how I did it…

1. Start Fresh. Question Everything.

I used to read non-stop about productivity. I still read and experiment with it — only now I have a clearer picture of what it looks like.

Do this, try that. Schedule this, snooze that.

I ended up with so many productivity hacks and exercises that I spent more time on them than actually getting shit done… you know, being productive.

So I dropped it. I dropped it all.

The reminders. The apps. The tasks. The bullshit.

I looked up the definition of productivity. Here’s what I got:

And since I’m not a crop farmer, I decided to define it myself…

Getting shit done that moves things forward

That’s what productivity is.

And with that, I began to build a personalized productivity system from the ground up, with a focus on moving things forward.

For everything I was doing, I would stop and ask,

“Does this move things forward?”

It’s a healthy exercise to do, even if you aren’t struggling the way I was. Audit what you do and ask why you do it. Over time things tend to pile up. It’s important to do some housecleaning once in a while.

So I cleaned house and focused on my new system. One designed to get important things done before dealing with anything else. One designed to optimize my time and my mind.

The rest of the list are the actions that followed…

2. “The Post-it System” and The Death of Digital To-Do Lists.

By questioning everything I did, one thing became abundantly obvious: I needed to stop using Google Inbox.

The reasons are detailed here: “Why I Quit Google Inbox”. And the most common question I’ve gotten since writing that is…

“So what do you do now?”

I use a Post-it note. Just one.

My new system

Digital To-Do lists can be endless. You can put thousands of tasks and reminders in there and have room for millions more.

On a Post-it, I can fit 3.

And so I write on it the three most important things I can do that day. They are prioritized based on their impact; #1 being the most impactful.

“Impactful” meaning it move things forward for the company or for me personally.

In my situation, these two blend…
Company success = personal success
Taking care of myself personally = I perform better for the company

I’m aiming for tangible progress. For movement forward. The Post-it provides the tactics to achieve this.

And notice the list is prioritized. Something digital To-Do lists tend to fall short on. Throwing reminders and tasks into an unordered list makes them all appear equal.

Sure you can call that important client -OR- you could quickly post a photo on the company Instagram. Either way you get the gratification of crossing something off the list. So you are actually incentivized to do the thing that is quick and easy. The reward is the same.

But the results are drastically different.

This mindset compounded over time derails your goals or, at the very least, significantly delays them.

The Post-it System has you force-rank the top three things that you need to get done. It provides focus. It advances your goals. It moves shit forward.

I create it at the end of each day.

And the next morning it sits on my desk, staring judgmentally until I cross off item 1. The visual cue is powerful.

I’m happy when I get to cross something off. It’s gratifying. Pursuing that gratification hungers me to start my day.

This strategy yields incredible results. Rather than trying to “build the wall”, I stay focused on laying bricks. I feel happy and accomplished each time I do. And soon — you start to see a wall forming.

3. The Morning Routine.

The Post-it strategy frames the entire system. Now let’s backtrack to the start of each day.

The first thing I do after getting up is make tea. I switched from regular coffee. While tea doesn’t give me the immediate energy spike, I’ve found it’s a more sustained charge and doesn’t make me crash.

This, coupled with some minor physical exercise (stretching, maybe pushups or squats), wakes my body up and gets my mind going.

Next I meditate for 10 minutes.
(Don’t ignore meditation. I’ve done it for a while and it was important to keep in my routine. I recommend Headspace to start.)

And immediately after that — I write.

I don’t write long but I force myself to get those early thoughts out. Some of the clearest, most creative thinking comes first thing in the morning, when you’re waking up, getting ready, or taking a shower.

It can be a blog post draft, a journal to myself, or some new idea related to work… it doesn’t matter. I want to get these thoughts down.

After all of this, I typically have about an hour before our regular team check-in. I’ll use this time to start, and maybe finish, item 1 on the Post-it.

4. Digging Into The Work.

Now it’s time for our meeting. We try to keep it to 15 minutes or less. Perhaps I’ll have another cup of tea (hardcore, I know).

I take notes during the meeting and catalog any needed followups. If I’m blocking someone — I do that immediately.

This is an important note.
Yes, in this case I am spending time on something that isn’t on the Post-it. But it’s important to get the team mobilized before working on my own tasks. The meeting already forced my mind to switch contexts. So it’s more efficient to stay in that context, take action, and get others moving forward.

Then it’s back to the Post-it.

Now I’m caffeinated, I’m intellectually stimulated, the team is mobilized, and I’m more than ready to tackle my list, one at a time.

Notice — I haven’t checked email yet. It used to be the first thing I did.

That comes only after item 1 is complete. At that time I will check email, take a walk (coupled with scheduled calls), and eat lunch. The afternoon is dedicated to items 2 & 3.

Don’t underestimate the power of walking

After those are done, I check with the team, look at email again, and use all of those inputs to create tomorrow’s list.

This email philosophy is very “Four Hour Workweek”, of course. That book is almost 10 years old but the principles are as sound and relevant as ever.

5. General Rules.

Stop procrastinating. Make decisions and take immediate action. Don’t “snooze” things that need to get done. Force yourself to be decisive — moving important things forward and cutting ruthlessly things that are not.

Prioritize yourself. Make happiness something you work on. It’s a state you achieve, rather than one that magically comes and sustains. Work at it. Take measures to do things that you enjoy and eliminate things you don’t. Be honest with how you feel about doing certain things. Cut out the ones you dislike. Make time for the ones you love.

Get rid of the negatives. This bears repeating. Stop doing shit you hate. Especially unnecessary shit. It can be people, tasks, or activities. Get rid of any that are negative. Any that make you feel bad. Ask yourself if it moves things forward. Ask yourself if you like doing it. It should only be done if the answer to one of those questions is “yes”. And if it does move things forward but you dislike it — perhaps someone can help, or even do it for you.

Set macro goals, create micro systems. My weekly goals became the end of me. I set too many. And many I set were unimportant but existed due to my necessity to be busy. They consumed me. Instead, I now set goals for the year. I then implement systems (a chain of behaviors and actions taken daily or weekly) that further those bigger goals.

Don’t suppress yourself. If there’s something you want to do or an idea you’d love to pursue — try it. Stop any thoughts that come about saying, “you can’t do that because of XYZ.” Stop that. You can. If it’s meaningful, make time for it. Prioritize it. Don’t suppress ideas… explore them fully. Let them run their course. That’s the only way they evolve and grow.

Most of this is simple but eluded me for so long.

I’m glad I’ve made these changes. They’ve had a profound impact on my life, both personally and professionally. But it’s all a work in progress. I’ll always try to improve myself — living in “permanent beta”.

Of course not everyone has the same commitments, goals, or life circumstances. Try your own version of this and see if you have similar results. When it comes to being happy and being productive — there isn’t one true answer. Pick out things you like and ignore things you don’t. If you’re self-aware and always strive to be better… you will.