The Three Phases of the Journey to Working For Yourself

Note: This is a guest post by Michael Hellerslien. He is an incredible coach, rising star and beautiful human being. I encourage you to check out his free video series here on unlocking your genius.

In order to navigate the journey to getting paid to give your gifts, it helps to have a roadmap.

This post gives you such a road map, allowing you to identify the stage you’re in, and see what’s coming down the road.

With a map in hand, you can see what’s coming, anticipate potential challenges, and not waste time jumping ahead.

Knowing what phase you’re in allows you to more easily lean in to it to properly prepare yourself. When you  acknowledge and honor where you are, you can devote yourself fully, and avoid painful backtracking, and constantly starting over in frustration.

Taking this approach, quitting the template and working for yourself is not so much about the external, as it is the internal.

The path to getting paid to be you is an introspective journey that leads to self-actualization. To successfully navigate this path requires an ever-expanding ability to be conscious of and deliberate about why we are doing what we are doing, whom we are doing it for, and how we are doing it.

When done properly, we find ourselves in alignment with our life’s purpose and our creativity is unleashed.

I have broken down this process into three distinct phases:

1. Cultivating an awareness of what is possible. The Curiosity Phase.

2. Testing our theories regarding how we can bring value to our audience. The Play Phase.

3. Integrate and internalize what we’ve experienced so we are able to create from a place of deep authenticity. The Creative Expression Phase.

This post sheds light on the treacherous rocks that commonly shipwreck entrepreneurs (e.g., the sense of being overwhelmed, procrastination and fear).

You are not alone on this journey.

All of us, at one time or another, have experienced limiting beliefs and unconscious holding patterns that have made us fear the blank, white page and blinking curser.

Do not fear, fellow trailblazer. When we fall down, our bloodied knees become an artifact and reminder of our courage.

And inevitably in the first stage, you must get your hands dirty.

Phase One: Curiosity

The first phase in becoming a successful solopreneur is about curiosity. Curiosity is built as we realize and expand our awareness of what is possible. But curiosity is a double-edged sword. The downside is confusion.

We are marketed to by snake-oil salesmen using devious tactics to up-sell us into buying expensive products that rarely deliver value. We are sold strategies that made someone a million dollars without any context for how that was achieved.

Disclaimers are turned into punch lines.

We become lost in a web of daydreams spun by the lure of an abbreviated workweek and location independence. Our dreams are used against us. We get caught up watching sales videos for hours at a time.

The interplay of human passion and technical skill dances in front of our eyes like Whirling Dervishes. Our heads are left spinning.

We start to lose track of reality and can no longer discern between fact and clever marketing. We pull out our credit cards and hit the big shinny “buy” button only to be disappointed, again.

But then, in our darkest hour, we might come across a heart-centered entrepreneurial guide, like Jonathan Mead, and realize that our stumbling around looking for answers was just a rite of passage. We had to go through this phase of development to recognize someone who actually advocates for us by showing us how to turn our dreams into reality.

Our hearts open. A warm feeling comes over us. We take a deep breath, gather our senses, and move forward along the entrepreneurial path.

Phase Two: Play

The second stage along the journey is play. We play both literally, by testing minimally viable concepts on our friends in the form of exploratory FB posts, and figuratively, by building mental scenarios of what it would take to support ourselves.

We start to find traction with our offer to the world only to second-guess our instincts. We experience fits and starts, over and over again. It is our nature to do so.

When I was young, I read Choose Your Own Adventure books. These books present the reader with a decision. If you choose one path you are directed to skip ahead to a predetermined chapter. If you choose another you are directed to a different chapter. The first time I read one of these books I stuck to my first instinctive decision. I was young and hadn’t had enough schooling to know any better. But as I grew older, a thought emerged in me.

The thought was, “Why should I settle for one plot line when I could have them all?” I began to second-guess my decisions, and rather than skip to the directed chapter I would read them all simultaneously. The story became hectic and I would start to get confused. Things would stop making sense. I lost track of what my options were and stopped enjoying the experience.

As an entrepreneur, we start to believe that feeling overwhelmed is an intractable obstacle. We gradually become cognizant of the fact that we need to start whittling down our options. We want to serve everyone but begin to realize the value in speaking to a defined audience.

We start getting coached one-on-one by experienced people. The energetic absorption of wisdom that occurs only through direct mentorship becomes apparent.

We begin to awaken our inner, goal-orientated and laser-focused entrepreneur…

Phase Three: Expression

In the final phase, our “why,” “who” and “how-to” fall into place.

  • Our “why” breathes life into our authentic voice.
  • Our “who” takes shape in the form of a well-defined customer avatar.
  • Our “how-to” turns into compelling blog posts, social media interactions and email opt-in sequences — all of which deliver incredible value to our audience.

This phase is simple, but far from easy.

To complete this phase we have to look fear in the face and laugh at it. To do this we have to overcome our ingrained resistance to breaking from the mold and become successful on our own terms.

Resistance has two fundamental components. The first is our attachment to the outcome, rather than an enjoyment of the process. The second is our fear of being judged, rather than cultivating an unselfconscious expression of creativity.

This resistance to our daily experience should not be taken lightly. Procrastination sinks ships.

However, it’s important to acknowledge and appreciate the darkness. It provides valuable contrast and unexpected opportunities.

Buddhist monk and Vietnamese exile Thich Nhat Hanh teaches us not to pass judgment too quickly. He tells a story about a person who was in a car accident. The person judged the experience negatively but then met the love of his life while in the hospital (paraphrasing). This passage perfectly illustrates the fact that it is not our job to judge, because we cannot understand what is waiting for us on the other side of the present moment. The car accident, in this case, was a blessing in disguise.

The second component, fear of being judged, is really a fear of success. This fear is deeply personal and mostly unconscious. The tools that we’ve learned to utilize when confronting this fear (journaling, morning pages, a morning routine and motivational affirmations) help us get past limiting beliefs, but do little to unearth unconscious holding patterns.

How my darkest moment led to my greatest breakthrough

In 2007, I left the corporate world believing that I had been betrayed by my bosses.

I was working for the fastest growing technology company in Oslo. Then, seemingly overnight, it collapsed like a house of cards.

I thought I was successful.

After all, I played by the rules and did everything right. I never imagined that my professional career would end with me acting as the key witness in a securities fraud case brought by the Norwegian government.

The shock and pain of this experience caused me to hit as close to rock bottom as I would ever want to be. However, just like the car accident story, there were unintended positive consequences of having gone through the ordeal.

I was able to let go of the idea that things should have turned out differently. I surrendered the self-conceited idea that I had been personally wronged. I transcended my ego.

When my day in court arrived seven years later I felt a stabbing pain in my lower back. There was a row of prosecuting lawyers to my left, a row of defending lawyers to my right, and a bench full of judges in front of me. Questions were being fired at me from all three directions.

In my periphery I could see my ex-CEO. I was no longer capable of anything but love for him. He looked like a child being scolded. I saw his humanity.

The stabbing pain in my back was a removal of the thought that success had been taken away from me.

I am aware of the danger of allowing such an experience to cause me to harbor a mistrust of people because I know, on a deep level, that I am already successful.

My inherent value as a human being is unquestionable. Writing a blog post that might be laughed at by self-conscious people no longer seems like much of a hurdle to overcome.

Bringing it all together for the heart-based solopreneur.

We each have our own set of limiting beliefs and unconscious holding patterns to overcome.

As creative, heart-centered solopreneurs it is our job to pay attention to anything that holds us back. In doing so, we find opportunities to learn, once again, how to trust in the flow of life.

We need to accept failure as just another challenge to overcome and to always remember this pivotal truth: it is not important that we fall, but that we get back up again.

The process to becoming a successful entrepreneur starts with unleashing the curiosity of our heart’s desires and continues with an unselfconscious expression of our authentic self to a targeted audience that admires our courage. The “how-to” falls into place now that we’ve learned to allow our path to effortlessly unfold before us.

Want to internally align with your life’s purpose?

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[…] The Three Phases of the Journey to Working for Yourself – Paid to Exist (This article is a wonderful road map of how to plan the journey of working for yourself.) […]


Hi Michael,

Great post. I think that phase one is the most important. If you develop curiosity you will eventually get to phase 2,3,4…. etc.

Funny thing is that most people never get to curiosity stage at all.

Danielle Louise Ross

Michael– Thanks for this post! You break down the incredible heart-based entrepreneur’s journey into digestible chunks that both sequential and true. Risky? Scary sometimes? Yes. But an amazing journey and so much joy and reward are available when we explore the possibilities, play, and express. Thanks again!

Chris Krohn

As an entrepreneur, I feel like I am in phase 3, but circle back to phase 2 from time to time. I see it as a re-visiting of what is possible, and that this is a necessary process for me to bring my evolving awareness to my clients. Great article. Thank you.

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