The Top 5 Things To Be Aware of On The Emotional Rollercoaster of Entrepreneurship

Anna Margolis
Transformation Agency
8 min readMar 31, 2017

As someone who left my corporate job as a lawyer 6 years ago, I can appreciate how much courage, consideration and introspection it takes to leave the stability of a regular paycheck and to step out of the Matrix.

After all, freedom isn’t as simple as announcing to the world that you’re on your own now and you’re ready to accept cash or credit card.

As easy as it is to romanticize the idea of freedom, especially if you’re stuck in a rut and are generally dissatisfied with your life, the stark reality is that the day-to-day running of your life and business is likely, at least for a little while, to go through a transition period that may be a long way short of the romantic ideal.

So, in the interests of supporting all you misfits, renegades and mavericks out there, here are the top 5 things to be aware of on the emotional rollercoaster of entrepreneurship.

1. Focus On Yourself

Let’s start where my co-founder James left off in his previous post
Where To Start When You Start Your Business In 1.5 Steps):

“Step #1. If you’re thinking about starting a business, shift your focus from the external to the internal. Focus on yourself.”

In his article James encouraged you to put your attention on what you LOVE, what you’re passionate about and what stirs your soul.

Here’s the truth:

“You can monetize just about any idea these days, but creating a business out of what you LOVE… That’s how you excel. That’s how you find the time and the energy. That’s how you’re going to play instead of going to work.”

2. Be Clear About Your Commitment

To be frank, if you’re looking to create independence by building a successful and sustainable venture, you’re going to need to be committed. As you’ve likely heard many times before, you’ll need to be more interested in focussing on the journey than the destination. And to prepare you for the trip, you’re going to need confidence and self-awareness, resilience and self-reliance, more humility and less hubris.

One thing’s for sure, figuring it all out isn’t easy and it’s inevitably going to feel like you’re jumping into the unknown. You’ll potentially be risking your money, your belongings, your reputation and sometimes even putting a strain on your health, so there’s no way to feel 100% ready, and if you wait until you are, you may never get started.

But if you allow yourself to believe that you’re entitled to do work that you love — work based on your unique gifts, talents, identity and values — work that’s fueled by your passion — you no longer have to live in a world where you are constantly chasing after other people’s ideals.

If you understand who you are and what drives you, you listen to your intuition and question conventional wisdom, set priorities and make thoughtful choices that support who you are and the life you’re creating for yourself, eventually you’ll figure out how to design a lifestyle that suits you.

But, before you remove a perfectly good source of income to pursue a life of liberation, take the time to reflect and be fiercely honest with yourself about your level of commitment, because rest assured that choosing independence is, at times, going to mean walking a high wire with no safety net.

3. Have Support On-Hand For The Emotional Rollercoaster

Once you decide to make the leap, how well you adjust to a life of independence will depend a great deal on your temperament, stamina and flexibility. You can’t really know what it’s like until you’re actually doing it. As such, it’s advisable to surround yourself with friends, coaches and advisers who have walked the path themselves and who have developed the emotional constitution to hold space for you to express your emotions, as and when needed.

Remember, self-reliance doesn’t necessarily entail self-confidence — and self-confidence is by no means a 24/7 state.

Quite simply, you don’t know what you don’t know and this will become rapidly and readily apparent as you progress on your entrepreneurial journey. One of the trade-offs for freedom is that you really have to put yourself out there and sometimes that can be a real emotional rollercoaster ride.

The best you can do is try to anticipate and prepare for the inevitable emotional discomfort you’re likely to face, recognizing that it simply comes with the territory, just as much as business challenges do.

Here’s a little heads up on some of what you can expect:

SELF-DOUBT

One of the biggest emotional obstacles, and possibly the most potentially crippling, is self-doubt. The thing about self-doubt is that you can’t side-step it or short-change it. First and foremost, self-doubt is part and parcel of being a human being; everyone has it and, whether you like it or not, it’s not going anywhere (at least not in the beginning).

The best way to arm yourself against the resistance that self-doubt presents is to recognize it when it strikes, make your way through it patiently and train yourself to function right along with it. Quite honestly, the best and easiest way to do that is with support; by working with a coach who can help you gain perspective and build your emotional resilience.

When you’re fending for yourself and dealing with various crises, sometimes nothing is more important than perspective, so it can be immensely helpful to have someone acting as a non-judgmental witness who can challenge your perspective and help you identify the Truth from the story you might be telling yourself in your head.

Alternatively, if there’s no support on hand in the moment, then you can always remind yourself of all the times you’ve felt afraid and done what you needed to do anyway.

FEAR (PARTICULARLY OF FAILURE)

Fear and resistance are innate responses that are triggered whenever we begin to reach for something that we truly want — especially when the thing we’re reaching for lies beyond our comfort zone.

In all likelihood, there will come a time when you find yourself driving the train without being able to see the track ahead, so ask yourself how confident you are that you can handle the consequences if everything goes off the rails.

In truth, you’re going to need to make peace with failure, because the fear of it — and the reality of it — may never leave you. Every successful business person has experienced their fair share of failures: near bankruptcies, inability to secure enough financing or just good old fashioned lack of customers.

You don’t just need faith in yourself and what you offer to develop the kind of invisible shield that protects you from taking the knocks and rejections personally. You also have to develop an almost forensic ability to view your missteps and failures objectively. If you can use your emotions as a guidance system that’s telling you something valuable, you’ll see more clearly what other variables are at play.

At the end of the day, it’s not the mistakes themselves that help you to hone your skills, rather it’s what you allow yourself to learn from the experiences and the degree to which you’re willing to grow from them.

After all, failure is rarely final; in actuality it’s just as easy to interpret it as a “not yet” or “not quite like this.”

4. Be Prepared To Be Misunderstood

If you’re doing something you love, be prepared (especially if there are other people that are financially dependent on you) for the people in your life to consider your endeavor as being downright irresponsible.

While you are falling in love with your business, unfortunately, to others it often appears that what you’re obsessed with is yourself. You’re so consumed with what you’re doing, and it’s so important to you, that you just expect others to understand and empathize. Yes, your business is the most important thing in your life, but it’s not the most important thing in everybody else’s.

At the end of the day, we choose independence to be more in control of our lives and that means taking full responsibility for it in every sense: professionally, physically, financially and emotionally. We are driven by a powerful guiding instinct; a bone deep need to strike out on our own and to turn our vision into reality.

And there are certainly significant benefits to going all in. When you’re company is well established, it’s a wonderful feeling. You’ve made it! And on some days, your heart will burst with pride watching the company you’ve created or the people you serve, blossom before your eyes.

But you will also have days that scare the living daylights out of you, break your heart and leave you feeling incredibly lonely. That’s why you need to be prepared to go all in on the commitment front — mind, body and soul.

So what if it doesn’t look like everybody else’s life? So what if others judge you for it? Who cares, when you’re building a life of freedom and independence.

The good news is that if you anticipate the emotional and psychological hazards ahead, you can adjust accordingly to avoid some dangers altogether and minimize the impact of others.

5. Recognize That We’re Not Built To Do It Alone

As smart as you are…..

As fast of a learner as you are…..

As diverse as your skillset may be…..

…..the bottom line is that human beings are relational beings, and we’re not meant to do these things alone. If we were then you would have all of the necessary skills and knowledge built into your system and you wouldn’t ever need to pay accountants, strategists, web designers or developers, tech support etc.

As Paul Cooper shared in his recent article the most important question that an entrepreneur must answer (or not) before starting a new business:

“At some point every entrepreneur is faced with the reality that they need support and that means adding more people to the equation.

For most people the answer is simply to hire someone.

But what does hiring somebody actually mean?

Hiring somebody means determining their salary.

Delivering that salary consistently.

It means being clear about what you need from the individual you hired and having the ability to create a healthy relationship with that individual such that your needs can be communicated effectively to them.

It involves creating a culture that inspires them to keep showing up and doing their best work.

It requires a new level of leadership from you as an entrepreneur.”

Whether you hire someone into your business full- or part-time, or you simply engage them as a contractor, no one can get away from the fact that we need other people to get sh*t done.

And given that that’s the case, it’s a good idea to be aware that our personal evolution happens through our relationships with other people. As such, you can EXPECT to come up against challenges in those relationships, quite simply because the challenges are designed to illuminate the places inside you that you still have room to grow.

Again, this is where having a coach can come in handy, because it’s extremely important and healthy for us all to get accustomed to letting our emotions flow freely so that we can start usefully using them as our internal guidance system in supporting us to make wise decisions.

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Finally, just a little word to the wise, creating your own business as a self-created, top-down hierarchical pyramid is tantamount to choosing to communicate with a brick phone over the iPhone 8 in an era when business experts like Gary Hamel, are making it clear that bureaucracy is an outdated hangover from the industrial age and is on the way out.

So, before you choose who you gather together in your team and how you organize your new venture, you may first want to check out Paul’s article.

Wishing you the very best of luck in your new venture.

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Anna Margolis
Transformation Agency

As a former lawyer, Anna merges material world memories, tales of transformation and embodied experience in articulating the future of collaboration