Selfpreneurship #1: This Dream Isn’t Going to Build Itself


No one will care about your dream more than you.

This article is about how you can start taking personal responsibility for where you want to be.

A little while ago I reached out to the Frontrunners community asking how I can help you all better move toward your dreams, goals, and preferred future. I got a lot of responses back covering a lot of different topics, but one area specifically stood out:

There are people out there who are trying to build a business who are running into some serious obstacles: feelings of self-doubt, struggling with internal motivation to make progress, freezing up when they're talking to prospective customers, feeling awkward talking about money, getting too bogged down by day-to-day life, not feeling credible or confident...

Let me tell you, I've been there.

I've done a lot of different kinds of business; from retail selling, to direct sales, being a tiny little piece in a really big corporation, working in small independent agencies, to being a self-employed brand consultant/designer and wearing every single hat at once: creative director, accountant, my own personal assistant, manager, production person, receptionist, tax-filer, financial planner, you-name-it...

And although self-employment has by far been the most challenging, it has been the most rewarding, the most freeing, and has grown me vastly more than I ever imagined. All of my other experience outside of it have informed my growth and given me perspective on the kind of life and priorities I have as an entrepreneur.

If there's one thing these experiences have given me, it's an appreciation of, empathy for, and a passion to help people who are in the process of pursuing a self-designed life, business, or dream.

Whether you want to start your own business, move up in the industry you're already in, pursue a non-business-related dream, or simply are passionate about personal development, the principles for growth, disciplines, and process for development are largely the same. I think the main difference is probably just the level of responsibility you are prepared to take on and the degree of control and freedom you want over your life decisions.

That being said, I'm going to start a series of posts that are focused on this concept:


aka: "Being Your Own Boss"

I'm going to focus on different facets of life surrounding designing a life you find most fulfilling (Freedom: that IS what we all want, right?), with some specific focus on building a business (since financial freedom is a key to most other freedoms).

Grain of Salt:  

I'm in the process too. And I'm writing this because I care, and I want to help – not because I know it all.

Please read this series with these caveats:

  1. I don't want to give myself the title of "Expert". Too many people assign themselves really fancy-sounding titles in hopes that the expertise will come as a result of the title. I believe in the approach of only assuming a title that you have earned through extensive experience.

  2. Experience DOES count for something. I've been a self-employed designer for the past 10 years. I've invested many thousands of hours into not just developing my skill set, but more importantly: learning how to be a business owner. And that's the difference maker between just having a skill set, and having a skill set AND being able to pay your bills and be in charge of your time AS WELL.

  3. I favor the approach of teaching as you learn. Why? Because all of us have something to learn, and should always be learning. Waiting for "Expertise" can be one of the biggest obstacles to starting. You only need a little more experience than someone else to help them. You only need to be one step in front of them to help them take the step you just took. I love coming alongside others. I feel it's a more transparent, relatable, and less-intimidating style of leadership than standing on a mountaintop and shouting directions all the way to people at the base. All of Frontrunners is an experiment in me teaching and sharing as I go. Take comfort in the fact that I'm just as scared, intimidated, and anxious for the future as you probably are. :)

Without further adieu, let's get started!

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Your Dream Isn't Going to Build Itself.

Many of us want the freedom to be in charge of ourselves, our time, our decisions... but given the opportunity, we don't know what we would do once we have it.

Too much freedom can be paralyzing sometimes.

The best part of self-employment is that you're your own boss, and the worst part of it is that you're your own boss.

What do I mean by that? This:

With great power comes great responsibility.
— Uncle Ben, Spiderman

As freedom and independence increases, responsibility increases. It's easy to complain about your manager at work when you're not the one who makes all the decisions, but when you're in charge things can be a lot more challenging. When you're the boss, you don't have someone expecting you to wake up early, or use your time productively, or take consistent daily action, or make progress toward a goal... that comes down to you. – When you're the boss, you can take as little or as long as you'd like to move forward.

  • You have to set expectations

  • You have to find our what kind of motivation works best for you: external or internal, or both.

  • You have to set goals

  • You have to master your time

  • You have to create a schedule

  • You have to create structure

  • You have to be disciplined

Let's face it, if you're self-employed, have a side-hustle (supplemental income), have dabbled in personal-development, are focusing on learning a skill, or are in any number of various pursuits toward something you desire, it's because you have a DREAM. You want to, in some way, shape or form, be better in the future than you are today. And if you can connect with this to even the smallest degree, you will want to stay closely in-tune with this series.

I once had a mentor ask,

"If your dream was your boss, would it fire you?"

Ask yourself this question. 

This reveals a crucial aspect of designing the life you want: You have to treat your dream like it’s your own business.

YOU are the owner. Everything rises and falls on your decisions. Arriving at the destination is fully-dependent on the actions you take. You've got to treat your dream like it's your job. But I don’t mean a soul-sucking job, because it’s not. Your dream is something you WANT, it’s something you ENJOY. It’s something that is FULFILLING. – It may be hard of you to imagine this if you’ve never had a job that was fulfilling before.

Being your own boss means that you have to SHOW UP. You have to WORK IT. You have to MEET GOALS and EXPECTATIONS. And that there are CONSEQUENCES for mistakes and REWARDS for succeeding.

As a business owner, you take more risk than anyone else, but you also stand to make a greater reward than anyone else. You have more responsibility than anyone else, but you also have more freedom than anyone else. You have to make more decisions than anyone else, but also, YOU get to make the decisions that affect your future, not someone else.

A lot of people SAY they want freedom, but is that what they really want?

I think what many people mean is that they want a free-ride; they want the rewards without the work, they want the goal without the process. But you can't separate them, they are inseparable.

If you don't have the right kind of mindset and discipline, freedom can be a dangerous thing.

When you're free to succeed, you're free to fail too. When you're free to make decisions, you're free to make both good and bad decisions. – Some people don't want that kind of responsibility. It scares them. They would rather prefer to stay in a situation where someone else makes all the decisions for them, every day. It's consistent, predictable, it feels safer that way... but it's actually a gamble. 

Our culture has conditioned us into thinking that entrepreneurship is "risky" and working for someone else is "safe", but let me ask you this: which scenario feels "safer"? :

  1. Someone else, whose primary goal is building THEIR dream, is in charge of your decisions and actions on a daily basis, in addition they determine how much money you're worth.

  2. You assume all responsibility for your own dream, make all the decisions you need to in order to get there, be in charge of your daily actions, and are free to determine your own worth and value.

Fear can be a powerful motivator.

It's a big reason many people choose to stay at a job as long as they can: because the thought of leaving to go somewhere else or to forge out on their own seems too frightening.

But I'd like to propose a frame of mind that uses that craving for safety as a positive fuel for action.

From the perspective I described in the previous paragraphs about what feels "risky", it's MORE risky to stay in the same place and hope that things stay the same, rather than taking action to get closer and closer to a life where you are more in control.

For me, I'm afraid of a life where I have no control; where I have to submit myself and my family to the goals and wishes of someone else who may not always have our best interests in mind. I'm afraid of ending up with the same fate that too many other people have: ending up 20-30 years down the road with limitations on my finances, time freedom, mobility, and having made compromises on the basis of survival rather than LIVING. I'm afraid of the possibility that if I don't take action in this season of life, that the future could look dramatically different than I dream it to be.

This isn't to say that I'm spending every day in bed, too stressed to go outside, pulling my hair out, and hiding under a blanket.

It's also not to say that I don't believe in having faith that the future will be bright and that everything will work out for good. I'm not advocating for a mindset of living in constant fear of the future, awaiting disaster, and worry that I have to do everything perfect or everything will crash – that's not healthy.

I'm advocating that we tap into our survival instincts: the type of fear that keeps us alive, keeps us healthy, helps us make decisions. Change our perspective of fear being something to completely avoid, and acknowledge it's usefulness when it's harnessed. And by all means, have faith and hope for the future, but faith must be paired with action in order to be effective.

If we can define a picture of our preferred future (vision), then we can define a picture of what we DON'T want the future to look like. USE THAT as a guide.

Evaluate your life and your decisions and see which "future" your path is pointed towards. If you're pointed toward the nightmare future, then you know to make some adjustments, if you're pointed toward the dream, then you're on track.

Use Your Resources Wisely

Sometimes we expect that because we have desire, time, and ideas that our dream will manifest itself automatically. But sometimes time just passes by itself, leaving you years down the road, no closer to your dream than when you started years earlier. 

The reality is that desire and time and ideas are just resources. Resources don’t act from their own free will, we must put them to work.

And if we don’t use resources, then they go to waste. If you buy lumber and a hammer and nails, it doesn’t mean that a building is going to magically appear in front of you – you have to put them to work. Buying more lumber won’t make the building get done any faster either. In the same way, having more time or desire or ideas won’t get you closer to your dream unless you apply action to it.

Earn Your Results

The payoff from your job is often in the form of a paycheck, the payoff from your dream is moving closer to the goal of the dream, which may be:

  • More income

  • Artwork produced

  • A greater skill set

  • Debt paid off

  • Weight lost or fitness achieved

  • Savings toward a home or a dream-trip

  • or many various other outcomes.

Sticking with this same analogy of treating your dream like it’s a business:

If you don’t show up for work at your job, should you expect to get paid?

No way.

You can’t skip out on work for a month at a time, then come back for a day or an hour and work for a bit and still expect to get paid full-time. But for some reason, we don’t apply this same concept to our dreams. We expect that we will “someday, somehow” get there, but without working for it. Or we have an expectation that we will accomplish it, but no plan: we will get around to it "when the time is right, or “when life isn’t as busy”, or whatever your “someday” reason is, only to find ourselves at that “someday” without anything to show for it.

We look back at our lives, bewildered and frustrated and think,

“How did I get here? Five/ten/twenty years ago, I expected to: have my own house by now, be debt-free, write a book, be fit... fill-in-the-blank”.

But the explanation becomes clear when we compare the amount of work we put toward that goal with the amount of time that has passed.


Put In The Time

It takes thousands of hours to build a successful business. Thousands of hours to make anything successful.

But we tend to give up WAY before we even get close to that mark.

Malcolm Gladwell hypothesizes that 10,000 is the number of hours someone must invest into something in order to master it. And for some reason we expect that spending a few hours every few months each year is going to cut it for getting to our dream.

Do the math:

Working on your dream 2 hours every 3 months. That's only 8 hours a year that you’ve put toward your goal. At that rate, you’ll have it mastered when you’re 1,250 years old! – Seeing as we haven’t yet discovered a way to live that long yet, you need to make a decision: Is this really what you want? And if it is, then you need to start taking it seriously.

It’s not how many years you’ve been doing what you’re doing, it’s how many HOURS.

-Dale Partridge

You have to be consistent. You have to take regular action in order to achieve the result you want.

The consequences of inaction are very real, and therefore very motivating. In the context of self-employment: if I don’t work then bills don’t get paid, food doesn’t get bought, I lose freedom over my time because I have to go work for someone else, I lose the freedom of spending time with my family because I no longer get to work from home, etc...


Too many of us are unsatisfied with our lives, and (at the core) it’s our own fault.

I don't say this to shame you; we're all already pros at making ourselves feel guilty. I know for me personally, sometimes I need to hear something I already know from someone else in order for it to sink in.

Our approach needs to change: 

We treat our dream/goal/business like it’s a test that we’re procrastinating for, and only take action when we feel guilty enough or when we’re absolutely forced to by circumstance.

That’s not going to work.

I was going to say that we treat our dream/goals/business like a hobby, but I didn’t feel like it was accurate enough because I think we dedicate WAY more time to our hobbies than we do to our dreams. If we were honest with ourselves, we spend WAY more time watching shows, playing video games, going out to eat, sleeping, or on social media than we dedicate to our dream. None of these things are inherently bad, the issue is that our priorities are imbalanced.

Americans spend an average of 4.7 hours per day on our phones, which is around 141 hours per month, and 1,692 hours per year. Compared to the few hours every few months we probably dedicate to our dream, if it takes 10k hours to master something, then we’re going to become a “Phone Master” about 200x faster than we will master our dream! – If you’re cool with that, then carry on. If not, then some changes need to be made.

Fill in the blank for your dream:

This ____ isn’t going to ____ itself.

  • This business isn’t going to build itself.

  • This book isn’t going to write itself.

  • This body isn’t going to tone itself.

  • This debt isn’t going to eliminate itself.

It’s up to YOU to take action toward it.

Treat your dream like a business. Become an entrepreneur. Become the CEO of yourself.

These are some reasons we don’t take consistent action toward our dream:

1. It’s hard.

Of course it is, so is your current job – except chances are you don’t even like doing that one as much! Wouldn’t you rather work hard doing something you love? Everything worthwhile in life is a challenge. “Only dead fish float with the current.” – The challenge is a sign that you are alive.

It’s ironic how hard we work at doing things we don’t enjoy because we’re afraid of losing them. But we don’t work hard at the things that could potentially be the most fulfilling to us, and by default of inaction we lose that instead. Work hard at the job that provides for your current needs, work even harder toward the job that you really desire to have, and it could eventually provide for your needs and more.

I’m an advocate for the idea that you can make a living doing what you love. Because if you love something, you will be good at it, and if you’re good at it, you will succeed, and if you’re successful, it will provide for your lifestyle. – It will require an uncommon amount of work, because making a living doing work that is fulfilling is unfortunately an uncommon concept for many people, but the rewards are worth it.

2. We lack personal motivation.

If you're not motivated for your dream then I would ask this question:

Is this thing really your dream then?

If it were, then you’d have motivation. If you’re not motivated, then revisit why you’re doing it in the first place. If you don’t have a heart-rooted reason why, then perhaps you should do something else. Either that, or you’ve never defined your “WHY”. In that case, you need to define the reason why you want what you want, the reason why you’re doing what you’re doing.

  • What will it accomplish in your life?

  • What effect will it produce for you, your family, the world?

  • What feelings will it give you when you succeed?

  • What need/desire will it fulfill inside you?

  • Who are you doing this for, and why is that important?

3. We wish someone else would motivate us to do it.

Some of this comes down to understanding yourself: are you the type of person who needs external motivation and accountability? Then get it.

But you cannot expect anyone else to become more passionate about your success than you, it’s not going to happen… unless you’re prepared to pay them money.

This is why people hire personal trainers or coaches: because they know they need external motivation to meet their goal; so they hire someone to motivate them toward their success. – There’s nothing wrong with this form of motivation, I would venture to say that most of us need external motivation. Just be prepared that it will be an investment.

4. We’re waiting for permission.

You don’t need permission to do what you find most fulfilling. If you really feel like you do, then I’ll give it to you right now: You have my permission to design a life that you love. There! You have it!

You don't need to cross a magical line to start. You don’t need someone else to tell you that you’re going to do great at that thing, or that you have finally ‘arrived’ at a level where you can do it. You don’t need to be part of a club, or have a certificate, or receive an award to be validated for your dream.

Your dream validates itself.

The fact that you have a desire to do that thing gives you the license to give it a go. If you want to write, then write. If you want to sing, then sing. If you want to sell a product, then start learning to sell.

5. We’re waiting till we’re “Good Enough” to start.

This is totally counter-intuitive. How can you become good at something unless you DO it? There is a massive difference between knowing and doing.

The only source of knowledge is experience.
— Albert Einstein

Take the term "Good Enough", and throw out all the other letters except for the first two: "GO". – Cheesy, I know, so just go for it before I have to come up with any more motivational wordplay.


If there's anything you take away from this article, I hope you've begun to form a greater sense of ownership and responsibility for where you want to be  in life.

And I want to encourage you that you CAN do it. And you don't have to have it figured out today, or this month, or in a year. I think the most successful people are those who have become comfortable in the feeling of having no idea what they're doing while remaining confident in what they do know.

I have a saying I came up with to encourage myself when I'm feeling stuck:

"When you don't know what to do, do what you know."

Give yourself grace with your process, and don't run from the process.

Embrace that responsibility, it's scary but it's also empowering once you discover that you're more capable than you thought. Your capacity will grow with experience and practice. I give you permission to take baby steps.

Call it "Entrepreneurship". Call it "Adulting". Call it an "Adventure".

Your dream isn't going to build itself.

be your own boss and build it.