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writers

Insidious little voice

I’ve noticed that over the past few months, I’ve lost some steam when it comes to sharing my writing online.

After taking time for some good ‘ol fashioned introspection, I’ve realized that it’s probably because I’m afraid that I am no longer doing something worth hearing about.

I know deep down inside this isn’t necessarily true, but it’s still a valid concern nevertheless.

Back when I was freelancing full-time, I was doing something that was out of the ordinary.

Now that I’ve been working a 9-to-5 while also working for myself, I’m experiencing a relative amount of stability for the first time.

Because of this, a small part of my feels that my insight may not be as unique as it once was or that it’s not as valuable to others.

If I drown out all of the other noise, I know this is simply that insidious little voice inside my head.

Even though I’m no longer working for myself full-time, I’ve still created my own professional path and this is something I imagine others might find valuable.

The hardest part is breaking everything down in a way that makes sense and is interesting enough for others.

When it comes to creating something for someone else, quieting this voice is nearly impossible.

In fact, the more experience you gain, the quicker you realize it’s not about silencing this voice at all.

Being a professional means learning to ignore it while moving forward anyway.

Indecision is still decision

I’ve been hyper-focused making decisions.

From taking inventory of my current decisions to making better decisions for the future, I’ve been doing my best to become more mindful.

Over the past few weeks, I’ve noticed something about myself that probably applies to many others:

I procrastinate with some decisions and immediately take action on others.

Can you guess which ones are which?

It’s probably pretty obvious - I tend to put off larger decisions that have long-term results and take action on those that are relatively easy and have immediate impact.

For example, I’ve set a goal to open a high-interest, online savings account in order to start a new emergency fund. This was almost a month ago.

Why haven’t I followed through yet?

Probably for the same reason most people use - I’m afraid of making the “wrong” choice.

It’s easy to forget that, in the grand scheme of things, indecision is still a decision. In fact, it’s the worst decision you can make because you aren’t owning the outcome.

Like most things, it’s a matter of simply making a decision and, if needed, tweaking it later.

Once you make one major decision, the momentum carries over to the next and, before you know it, each one becomes a little easier.

A harsh realization

Like most weekend mornings, I’m sitting here in the corner booth of a local coffeeshop, going through the paces of my morning routine.

While journaling this morning, I came to a pretty harsh (yet fairly obvious) realization:

I can’t do everything if I ever want to do anything extraordinary.

I know, I know. This isn’t anything revolutionary, but like most epiphanies, we come to them in our own time.

In today’s world, one of the hardest things to accomplish is focus.

I’m not talking about overcoming normal distractions like email and social media. I’m referring to identifying one long-term goal, breaking it down into short-term steps, and focusing on each one at a time.

Add the crippling, self-imposed pressure of mastering everything you try and it’s baffling that anyone gets anything finished.

Like many “creatives,” I’ve always prided myself on my ability to juggle several projects at the same time. From writing to illustrating to launching my own products and services, I’ve tried a little bit of everything.

If I’m being brutally honest, this is the very reason I’ve never reached a level of mastery with any of it.

At the end of the day, going all-in on any one thing scares the shit out of me thanks to one very real question:

What if I miss countless other opportunities simply because I chose to put all of my eggs in one basket?”

I’ve realized this is the wrong question to ask.

Instead, I should be asking myself, “How can I possibly carry all of these baskets anywhere without dropping them?”

I think I’d rather make extraordinary progress on one thing instead of making very little progress on many.

The one thing

As I’m reading The ONE Thing by Gary Keller and Jay Papasan, I’m starting to realize a hard truth.

Since starting my daily writing routine over three years ago, I’ve identified and written down one specific action for me to take each day. In my mind, this is one action that will make the biggest difference in working towards the future I want.

If I’m being honest with myself, I’ve realized that even though identifying one specific action is better than nothing, I haven’t really been identifying the right daily action.

Instead of looking ahead into the future, identifying a clear purpose, and reverse engineering it into a set of priorities (or dominoes as Keller describes), I’ve been going after low-hanging fruit.

Basically, I’ve been taking action steps that seem productive day-to-day, but in the grand scheme of things, they are leading me into a very nebulous, unknown future.

This has been a great habit to practice, but without the long-term purpose or direction, it’s simply leading me towards more uncertainty.

Thanks to this book, I’m starting to focus on bringing the future into the present.

My argument for freelancing

After reviewing portfolios at a local design student conference, one of the students reached out to ask about how to price her first two freelance projects.

As we discussed charging per hour versus a flat project fee, including taxes, and other important considerations, she mentioned that one of her professors suggested staying away from freelancing right out of school.

I get it. What educator in their right mind would openly advise their students to take such a risky step straight out of the gate?

I’ll tell you who - someone who knows what is actually going on in the real world.

At this point, over 43% of the U.S. workforce is considered subcontracting or freelancing and that number is only going up.

Admittedly, many of these people essentially work full-time for companies that don’t want to give them the status of “employee” and others operate in the “gig economy,” but there are more and more creative professionals who are choosing to go their own direction.

Thanks to the democratization of software like Quickbooks, Stripe, Squarespace, and countless others, freelancers can fill in their gaps for little to no cost, which helps to take some of the risk out of the equation.

Sure, there is still an inherent risk that comes with working for yourself, but there is also inherent risk with relying solely on one source for your income.

Whether you’re gigging on the side or going all-in, laying the groundwork for a freelance career will never be a bad idea.

Clearing the mental queue

Whenever I feel stressed out or overwhelmed, I can usually narrow it down to one main reason:

My mental queue is jam packed.

Imagine your mind as an inbox that is overflowing with outstanding priorities, goals, calls, meetings, errands, and countless other distractions. I’m sure most of you don’t have to imagine - in today’s crazy, technology-driven world, this tends to be the default.

Honestly, this is how I feel a lot of the time, especially when I forget to check in with myself.

Whenever I forget to groom my mental queue, it quickly fills up with outstanding commitments.

How do I stop this from happening?

Like most things, it’s simple (I didn’t say easy).

As someone who regularly suffers from paralysis-by-analysis, I have to actively force myself to make decisions, pull triggers, and push stuff out of the door.

In other words, I have to clear my mental queue.

This involves actively mapping out all of my commitments, deciding next steps, and holding off from taking on anything new.

When I don’t do this, I tend to procrastinate and overthink things, which leads to even more stress and less mental bandwidth - it’s a vicious circle.

If you haven’t recently, make a quick list of every single commitment you have and ask yourself, “Does this belong in my mental queue?”

All-in is all wrong

As someone who was recently on a panel that gave feedback to entrepreneurs, I was asked, “Why are entrepreneurs taking advice from full-time employees?”

The first thing that comes to mind when I hear this is the “all-or-nothing” mindset that continues to permeate entrepreneurship.

Sure, there is no shortage of stories that tout a “rags-to-riches” rise to success for entrepreneurs all over the world, but that is exactly what they are - stories.

Over the past decade of full-time freelancing and entrepreneurship, I learned that living life in the extremes is usually a dangerous place to operate. If you’re not prepared, it can be lonely, stressful, and even lead to harmful thoughts of self-worthlessness.

I’ve always been a trial-by-fire kind of person who does better when there isn’t a safety net, but I’ve gone all-in before and honestly, it doesn’t always have to be this way.

I’ve come to terms with the fact that there are countless ways to create your own path.

Going back to the above question, I truly believe that you can always learn something from the person in front of you, no matter how different they may appear to be.

Why are entrepreneurs taking advice from full-time employees? Because many employees have experience with budgets, timelines, product validation, scalable (and unscalable) business models, bringing products to market, and simply talking to other people.

Just because they choose to work for someone else doesn’t mean that they don’t have relative experience to share. In fact, they may have the missing piece to the puzzle you’re trying to solve as an entrepreneur.

The sooner we can dial down the extremism of entrepreneurship, the better off we’ll all be.

Organizing the chaos

I’ve learned over the years that organizing the chaos of everyday life is one of the hardest parts of being a functioning adult.

Whether you work for yourself or within a larger company, distilling conversations, meetings, and opportunities down into tangible action steps is an art that, unfortunately, isn’t taught in school.

We’re taught how to “think critically” about writing and literature, but not about how we turn long-term priorities into short-term steps.

That’s why if I could create the curriculum for one course taught all over the country, it would be “Organizing the Chaos 101.”

It would be an intro course that presents frameworks, tools, and resources for creating your own accountability system. It might even explore various people and how they approach accountability.

I’m not usually a fan of looking backwards, but I can’t even imagine how much more I would have accomplished by now if I had created my own task management process sooner.

At this point, I’ve meshed my personal and professional lives together by mapping out long-term priorities like getting married or writing a book and breaking them down into smaller, more actionable goals, like booking a venue or finishing the first draft one chapter at a time (all using one Trello board).

As always, I’m constantly tweaking and updating as I come across other processes that work.

How do you manage your long-term priorities and short-term goals? How long did it take to get to this point?

Adopting a "one less" mindset

Like many people who struggle with bad habits, I’ve developed a “one more” mindset over the years.

Without even thinking twice, I’ll have “one more” drink, stay out “one more” hour, or try to squeeze in “one more” task while I’m working.

What’s the harm in this?

Like most things, it wouldn’t be that bad if it was just once in a while.

Unfortunately, it isn’t just once. These moments of “one more” compound on each other and end up biting me in the ass. One more drink + one more hour out with friends = one less productive morning.

Instead, what would things look like if I focused on developing a “one less” mindset?

I would probably feel a little better if I had one less drink, I wouldn’t be as grumpy if I spent one less hour out, and I definitely wouldn’t be as stressed out if I took on one less obligation - I would have way more mental bandwidth for the things that matter most to me.

The question is: how does someone adopt this “one less” mindset when they’ve built up a series of unhealthy habits that make it easier to say, “I’ll have one more…”?

I’m not exactly sure yet, but this is a question that deserves at least one more minute of my time.

Altruism and profit

Last night, I had the opportunity to be a panelist at a pitching event where local entrepreneurs present their businesses and ask for feedback around one specific question.

When it came to the final pitch, an interesting conversation popped up.

The entrepreneur mentioned they were including an altruistic component to their business model and one of the other panelists responded by saying, “You can focus on being altruistic once you scale up. As a startup, you need to focus on making mountains and mountains of big, ugly money.”

Maybe I’m just naive, but I couldn’t agree less.

Sure, if you want to eventually become a fully-sustainable company, you have to (eventually) have revenue coming in, but the idea that altruism and profit are mutually exclusive is ludicrous.

One of the smartest things you can do when starting a company is to focus on growing a community around your company.

Can you guess one thing people care about when it comes to the brands they support and the products/services they purchase?

A cause.

In today’s world, it’s becoming harder and harder to differentiate based on product alone. You have to plant your flag and stand for something when others may not.

If you ask me, doing good will always be good for business.

Customer service no-nos

I don’t care what industry you work in. If it involves working with people, you’re in customer service.

When meeting or talking with a potential customer or client:

  • Stop asking leading questions simply for the sake of appearing smart as you reveal your answers. They trap your potential client and make them feel dumb. If they knew the answers, they probably wouldn’t be talking to you.

  • Stop waiting for your turn to speak and start listening with the intent to understand the person in front of you. They’re talking to you because they have a problem and you (might) have the solution. Let them tell you what they think the problem is.

  • Stop using industry jargon and buzzwords that confuse people. If you truly understand what you’re talking about, you will be able to break it down and make it accessible to anyone. Even your grandmother.

  • Stop making assumptions even if they are only your mind. You may think you know the person you’re talking to, but in reality, you don’t. They are different from every other potential client you’ve met in the past. Treat them as such.

  • Stop focusing on short-term results during the conversation. If you do your job right, they’ll come back, even after talking to others. When you’re narrow-minded, it shows.

The 85 Percent Solution

I recently finished reading I Will Teach You to Be Rich by Ramit Sethi.

I know what you’re thinking, “Wow, you got suckered into buying and reading a book with that title?!”

First of all, it was gifted to me after accepting my first full-time position and second, I honestly wish I would’ve read it a decade ago.

After moving past the seemingly shallow title, I learned so much about:

  1. Optimizing credit cards

  2. Setting up no-fee, high-interest bank accounts

  3. Opening investment accounts

  4. Creating a conscious spending plan

  5. Automating the entire process

  6. Learning how to pick the right investments

Outside of these six steps, one of the most helpful insights I learned was “The 85 Percent Solution.”

In Ramit’s words, it’s basically the idea that “getting started is more important than becoming an expert.”

After reading this, I realized that this not only applies to finance, it can be used in any area of life.

Whether you’re a writer, a freelancer, or a new entrepreneur, putting something in place that works is much more important than getting it “right.”

Your idea doesn’t have to be fully fleshed out in order for it to be valuable to someone else.

In fact, I bet there are plenty of people out there who need an imperfect solution now instead of a perfect solution later.

85 percent isn’t 100, but it’s better than zero.

Clear and concise

When it comes to the ability to be clear and concise, some people are born with it and some people are me.

I’ve never been the most straightforward.

Instead of getting to the point, my point usually arrives within the last 5% of any conversation, which means I (usually) have to fumble my way through logic and reasoning until I, after thinking out loud, can put two and two together.

I’m not exactly sure why I’ve always been this way, but it’s something I actively try to improve upon.

Speaking of improving, I can confidently say that writing has made the single greatest difference in becoming more clear and concise.

I’ve been writing (almost) every day for over three years now, and I’ve realized something interesting - Communicating with others has become easier because I’ve already had many of the conversations beforehand with myself.

Thanks to this unexpected side effect, I’ve already thought about many of the responses I give. It doesn’t mean they’re polished and contrived - they’re just a little more clear and thought out.

This is one of the biggest reasons why I urge other people to consider writing, even if no one else will ever read the words they write in a journal.

Practicing leadership

At this point in my life, I’m ready to be a leader.

You might be wondering, “What makes you qualified to lead others? The fact that you’re yet another white, entitled male who feels as if he deserves it?”

I promise it’s not this simple.

From freelancing full-time to co-founding companies with others, I’ve spent the past decade fumbling through the process of creating my own path and I’ve learned a few things along the way.

First and foremost, I’ve learned that leadership isn’t about dominance or having the right answer - quite the opposite.

Some of the best leaders take a much different approach.

Instead of telling others what to do, they lead by example. They know their actions speak louder than any of their words and they do their best to align these actions with the things that truly matter.

Instead of taking credit for the accomplishments of their team, they know that credit for one person depletes ownership by many (Thanks Scott Belsky for perfectly capturing this idea using these words).

Instead of being the first and loudest person to talk, they listen first with the intent to understand. They are self-aware individuals who strive to be empathetic towards everyone, especially the people on their team.

These are just a few of the many ways in which great leaders facilitate great teams and honestly, I’m ready to roll up my sleeves and show that these things truly matter to me.

Being an ally

I’m lucky that I get to work with a company that values having intentional conversation around what it means to be diverse and inclusive.

Each month, some of us meet at a different coworker’s home for an event called Homecoming where we discuss specific topics and share personal stories.

Last night, we talked about what it means to be an ally.

As someone who usually falls into the privileged majority in almost any situation (a straight, white, cisgendered male), I want to be an ally for individuals and groups who aren’t so lucky.

Admittedly, I don’t do nearly enough, and usually for one reason - I struggle not with what to say, but how to say it.

Sure, I understand that in the real world, you don’t get a gold star for doing the right thing. Speaking up for others (when that is in fact what they want) should be a given and we should just be able to do it.

The thing is, I also understand that we’re human, which means we’re messy, imperfect creatures that fall back on habits when shit hits the fan.

I’ve learned that if you really care about making a change, you have to consider the habits that drive (or don’t drive) your actions.

In my case, I’m focused on developing the habit that when I hear or see something that could be considered discrimination or injustice, I first ask the person being discriminated against, “Hey, are you OK? How do you feel right now? What do you need?”

As we talked about last night, not everyone wants or needs to be saved. As someone in most majorities, I’m sure it can be much too easy to default to a savior complex.

I’m looking forward to continuing these conversations and doing what I can to become a more effective ally.

Culture is inevitable

I’ve been thinking a lot about culture over the past few months.

From joining a larger company culture early on to helping shape it on a smaller scale within my own company and a cappella group, I’ve noticed something that is probably self-evident to most:

Whenever you have two or more people working together, culture is inevitable.

From the tone and topics of conversations to the way in which you make decisions, culture simply happens.

In the same way that indecision is still a decision, not intentionally crafting your culture will still give you a culture, it will just be one in which you won’t have any control.

That is why I’m learning to pay more attention to my actions and how they affect the people around me.

Ultimately, these actions contribute to the collective culture.

Believe it or not, when I respond to a Slack comment with a specific GIF or an emoji, this becomes part of the documented culture.

When I have certain conversations within earshot of others, this becomes part of the undocumented culture.

It’s easy to forget these things when we prioritize our work over the people doing the actual work.

In my mind, mindfulness should be just as important as margins, more urgent than email, and prioritized just like profits.

How are you contributing to your company culture?

Content with being content

I was lucky enough this weekend to grab coffee with a friend who was in town for a wedding.

Whenever we get together, we have great conversation that leads to more questions than answers and enough ideas to fill a notebook.

Our conversation was based around my friend leaving St. Louis and his realizations since then.

He shared how even though he was looking for a professional change, he missed how his days were filled with things and people he cared about.

In other words, he wasn’t content with being content.

This is something a lot of us deal with, especially in our professional lives.

We feel pressure to “do more” and “be better” all while searching for something that fulfills us.

It’s no wonder social media can be a blessing and a curse.

It allows us to share our story and stay connected with the people we care about, but it also sets unrealistic expectations.

Not everyone has to travel the world, vlog every second of their life, or share an endless stream of filtered selfies. We don’t always have to strive for perfection.

In fact, I’m learning that being imperfect is far more interesting.

In a world where anyone can be anything, the people that stand out are one thing above all else - themselves.

Luckily, I have friends who help remind me of this.

Pleasantly surprised

We’re only five days into the new year and I have to say I’m pleasantly surprised.

Usually, it takes a few weeks to really feel the effects of a new year: the high you get from working out, the sense of accomplishment from creating a morning routine, the wicked hangover you get after celebrating a little too late the night before.

In this case, things are already taking off.

If I had to pinpoint one reason, it would probably be thanks to last year’s decisions.

Instead of focusing on quick actions that provided short-term results, I did my best to look further ahead and prioritize things that would have a better long-term effect (all while dealing with a cornucopia of shit).

Now, I’m not saying everything is falling into place - far from it.

In fact, I have yet to draw out my priorities for the new year.

I’m just noticing that for the first time in my life, I am actually OK with where I am.

I’m not complacent or apathetic - I’m simply content for the time being.

For all of you out there who are your own harshest critics (like me), take a moment and think back to the last time you felt this way.

I’m assuming these moments are few and far between.

When they do pop up, bask in them because, as you can probably guess, they tend to be fleeting.

Dragging my feet

It’s January 2nd and I don’t have any of my priorities written down for 2019.

Normally, I would be kicking myself in the ass for dragging my feet, but this year, I’m trying this new thing where I give myself more of a break.

I’m not exactly sure why, but I tend to have unusually high self expectations.

I know what you’re thinking: “Great, just what the internet needs! Yet another (bearded) white dude bragging about how he is special.”

I promise it’s not like that. In fact, instead of a badge of honor, it’s more of a curse.

With me, I’m either productive or lazy. Happy or sad. Driven or complacent. There really isn’t much gray area.

In the past, I’ve found myself frustrated and disappointed far too many times simply because I wasn’t able to meet every single goal I put in place.

This year, I still want to set goals, I just want to create them within larger priorities and make them more realistic and sustainable.

With this combination, I’m hoping this year will be less frustrating and even more impactful than 2018.

The highest of highs...

It’s the last day of the year and, like many people all over the world, I’m reflecting on 2018 while also thinking ahead to 2019.

After doing some thinking, I can’t deny that 2018 was the most defining year of my life (so far):

Highs: Traveling abroad with my girlfriend for the first time, proposing to her in Ireland, surviving my first year in business with Viabl, getting Dobby (our little fur baby), taking my first full-time position with Slalom Consulting, and finally reaching some amount of financial stability.

Lows: Financial issues due to higher freelance taxes than expected, multiple hospital visits while in Ireland, prolonged health issues likely due to stress, the failure to manage that stress because of an inability to consistently work out (thanks to the health issues), and losing some part of my old identity.

As you can probably guess, this year was filled with the highest of highs and the lowest of lows.

One of the most impactful lessons I learned was that health affects every aspect of life. When your health is in jeopardy, you also lose the peace of mind that allows you to think and live intentionally.

Now that I’ve reached a point of relative stability, my focus for 2019 is on helping others not only reach this point but to also thrive.

I’m still figuring out what this looks like, but all I know is that as hard as this past year was, it forced me to take a good, hard look at myself and make some hard realizations.

I lost my identity as someone who was freelancing full-time but found another one as someone who is piecing together their own path in their way.

I’m not sure what 2019 has in store, but I know that whatever it is, I’ll be ready.