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Entrepreneurship

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?

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.

Screw my ego

Something strange happened a few days ago: I felt a little twinge of resentment.

In the moment, I was frustrated with my own inability to take ownership over a new project.

However, after taking a few moments to look inward, I realized I was projecting my own insecurity onto someone else.

As someone who worked for myself for almost a decade, I got used to taking 100% ownership over any project I started.

As great as this may sound, this isn’t how things happen in corporate America.

People work in teams and those team members are collectively responsible for the overall success of the project.

Unfortunately, people tend to forget (like I did) that everyone on that team has something to learn from everyone else, whether it’s directly related to the project or not.

Like most people in a professional setting, I feel a need to prove my value.

However, I care way more about creating successful outcomes than I do about stroking my own ego.

At the end of the day, I’m part of team which means sometimes taking a back seat and learning from others.

Make less commitments

At this age, I take commitments very seriously.

When I give someone my word, I try to do whatever it takes to back up that word with action.

Sure, there are times when things get in the way. After all, part of being human is being imperfect, which means we take on too many commitments, set unrealistic expectations for ourselves and others, and we let our optimism get the best of us.

As long as this is the exception and not the rule, I’d say this is just fine. We should strive to either keep all of our promises or focus on the quality of our commitments instead of the quantity while knowing full well that we will sometimes fail.

No matter how much we learn, no one actually enjoys failing. It’s messy, uncomfortable, and it forces us to admit we were wrong.

The thing is, it’s OK to make mistakes because that’s when we learn the most.

Most people would probably agree that the one thing we shouldn’t do is to continue making the same mistakes. Not only is this disappointing, it means we aren’t learning.

Moving forward, I’m doing my best to make fewer promises while also making new mistakes. This way, I can devote my time and attention to fewer commitments and learn from the past.

Taking a break

I’m sitting at my kitchen counter, thinking about this long Thanksgiving weekend, and I can’t help but notice a huge difference.

In the past, each day of this break has felt the same. When I was freelancing full-time, I was never able to fully appreciate each of these days with loved ones - I always felt as if I should be working or making progress towards something bigger.

This year, I’m thankful for stability. It has always been an abstract idea that I strived towards, but I never really knew what it looked like until now.

It means the peace of mind to spend quality time with the people you care about. It means not letting stress infect every part of your life. It even means being able to show the people you love how much you care about them.

I will always strive for something greater, but during this long weekend, I am able to pause and give thanks for the fact that the people I care about are safe, happy, and healthy.

I can’t think of a better way to take a break.

A significant shift

There has been a tangible shift over the past few years.

As I catch up with friends who live in different cities, I’m noticing that more and more of them are dipping their toes into the worlds of freelancing and entrepreneurship.

I’m hearing origin stories that include turning a previous employer into a first client, partnering with a significant other, and even catching a big break after sharing some work online.

I don’t really believe in blanket statements, but if you think this is simply a fad, you’re dead wrong.

At this point, over 43% of the U.S. workforce is subcontracting and that number is only getting larger.

Sure, the gig economy plays a large part in all of this, but there is also a huge shift in mindset.

People are tired of working their asses off for companies that don’t appreciate the value they bring to the table.

I’ll admit - I was extremely lucky to find a progressive company like Slalom Consulting that embraces everyone’s individuality while working towards a collective goal.

I feel like this sort of progressive mindset is rare, especially in the Midwest.

Whether you’re working for yourself or looking to align with a company, think about the things that matter most to you in the long-run.

Otherwise, you’ll probably remain unsatisfied and uninspired, no matter where you work.

Me versus we

I met someone new for coffee last night and, as we both agreed, it wasn’t weird.

This might be an unusual way to look at it, but even as an extrovert, I sometimes feel uncomfortable meeting new people.

In this case, I met with someone who has also been in the St. Louis design/marketing industry for a while. We shared our stories, talked shop, and touched on some of the problems St. Louis is trying to solve.

One of his biggest questions right now is, as an independent professional, should he brand himself as a one-many army or an agency. In his words, he was debating on “me versus we.”

For many independent creatives, this is one of the toughest hurdles to overcome in the beginning. The thought of a potential client not taking you seriously because you’re on your own can be paralyzing.

I dealt with this same question when I was first starting my full-time freelance career.

Since radical transparency has always been a core value of mine, I decided to brand myself as the individual I am instead of “hiding” behind a brand that seemed bigger.

When tackling this question, the most important question to ask yourself is what matters most to me?

Is your goal to scale and work with others from the get go? Then maybe a bigger brand is right for you. Do you want to communicate a more person, one-on-one relationship with your clients? Then create a personal brand that reflects what matters most to you.

At the end of the day, there’s no silver bullet to any of this. You have to make your own decisions (and mistakes) and learn from them.

When it comes to solving the problems of others, it doesn’t matter if it’s “me” or “we.”

The focus should be on “us.”

MBA the hard way

There have already been so many opportunities for learning and growth at Slalom.

One of the newest is a series of talks called “MBA the Hard Way” where consultants share their entrepreneurial experience with other consultants.

Last night, we heard from someone who made the hard choice of leaving his start up in order to join Slalom. Like many of us who have worked for ourselves, he had to make a personal sacrifice in order to provide for his family.

I don’t have kids (except for a little fur baby), but I do know what it’s like to give up complete autonomy in hopes of a better life in the future.

Before I came to Slalom, I was a decade into a full-time freelance career and honestly, I wasn’t really sure why I was still doing what I was doing.

Thanks to a series of conversations, I realized I could still create my own path as a consultant, but I would be able do so in a more intentional way

This didn’t make the decision any easier.

As a freelancer or entrepreneur, it can be way too easy to attach your identity to your work or your company. When you have to give it up to do what’s best for you or your family, it can feel like a part of you is gone.

The hardest and probably most important realization is that you are not your work. You’re also not your company. These things are byproducts that come from your actions and efforts.

It’s important to remember things will always change and new opportunities will always come.

What one decision can you make now in order to impact your future the most?

Asking for permission

I don’t know about you, but I’ve always been somewhat of a people pleaser.

Growing up, I would do whatever it took not to make people like me. I couldn’t stand it if someone had even a tiny issue with something I was doing. Sometimes, I would even refrain from sharing my ideas just to avoid stepping on the toes of others.

As an adult (some would argue this), I can confidently say this is no way to live your life.

In fact, I respect others more when they aren’t afraid to share who they truly are with me.

Part of shedding this unhelpful mindset is giving up the need to ask permission.

Luckily, Slalom (my new job) is helping me with this. When someone has an idea or suggestion here, they don’t ask for permission. They ask for feedback.

There is a huge difference between the two. When you ask someone for permission, there is a good chance you’re asking the wrong person. Sure, maybe you need some funding and your boss is the gatekeeper, but ultimately, you are the only person getting in your own way.

Instead, when you develop a comprehensive plan and ask for feedback, you’re taking action. You are showing instead of telling, which communicates that you’re serious.

This isn’t easy. When you share your ideas, there will always be naysayers who jump at the chance to shoot down the ideas of others. That’s usually because they’re too afraid or insecure to share their own.

The more I think about this, the more I’m reminded by a small piece of advice my dad gave me a long time ago:

“It’s always easier to ask for forgiveness than it is to ask for permission.”

My role model

My dad has always been my role model.

Not just for his intelligence or sense of humor, but for his uncanny ability to combine both in order to make things more accessible to others.

I could not have been more proud to see him demonstrate this last night as he accepted the Washington University in St. Louis 2018 Chancellor’s Award for Innovation and Entrepreneurship.

Watching him recap his past 40 years of research (with a hilarious violin accompaniment) really did put things in perspective.

Creating a lasting, positive impact takes patience and help from others who are willing to be in it for the long haul. It also takes a seemingly impossible skill of balancing uncertainty while focusing on a single, clear goal.

Cheers to him and everyone else who has helped build and grow Arch Oncology and YourBevCo from the beginning!

A list of good questions

I’ve always prided myself on asking good questions.

If I had to guess, I would attribute this to my natural curiosity and drive to understand others.

This is probably one of the reasons I recently took a consulting job with Slalom.

At the end of the day, a good consultant has the ability learn about their client and their client’s problems and needs by asking good questions.

A good question isn’t hard simply for the sake of stumping others.

It does one thing above all else: it forces the person answering to think differently.

Here is a list of good questions I’ve been pondering recently:

• What does my future look like in five years?
• What is one action I can take today to live a more intentional life?
• When was the last time I applied critical thinking to my life?
• What are my core values and how am I living them day-to-day?
• What does success mean to me today? Tomorrow? A year from now?
• Why do I still practice unhealthy habits? How can I reprogram them?
• If I had an ∞ in my bank account, what would I do differently? The same?
• How can I help others with my unique skills and abilities?
• How can I make the world a little smaller?