The idea of starting your own business can be a sexy one. I daydreamed often about what it would be like to start my business when I was immersed in my corporate career. All told I spent over 13 years working in a big company, Microsoft Corporation. Now I’m a solo entrepreneur.

Before starting my company I spent 18 months traveling the world and living out of a backpack. My wanderlust ended this year when I decided to be my own boss.

I’m now well into the journey of creating my own business (creatively called “Raman Coaching”). It is a coaching company whose mission is to help motivated professionals in advancing their careers while living high quality lives.


Along the way I’ve learned a lot. I realize that it’s nothing like what I thought it would be. This blog outlines what its been like for me to have left the safety of a salaried corporate job to venture out on my own.

If you are a solo entrepreneur, or dream of being one someday, I highly recommend it. Just be prepared to have your world rocked!

1) Progress is not linear

In January 2015 and I whipped up a business plan. My plan took into account the fact that I was still going through a training to become an executive coach and assumed that it would take a few months to build my business to a sustainable level. Turns out that all of my assumptions were wrong!

I found my first two clients very quickly. Then it was radio silence for months as I struggled to connect with people and face my fears. It wasn’t until well into the summer of 2015 that I started growing my business to the point where I knew it could actually be a viable enterprise. Progress was not linear. Not even close!

Once I identified the things that were holding me back progress was swift. Later in this blog post I will articulate what was holding me back and how I was able to get past it.

2) The possibility of unlimited upside

Unlike my corporate job which was bounded by the trappings of procedure, annual reviews and approved salary bands; my own business has no bounds. Whatever boundaries that exist are my own creation.

This potential for unlimited upside, and the ability to create a business of my own choosing is an incredibly powerful motivator. I get to decide the measures of my success. I get to decide how I wish to prioritize financial gain versus free time. I get to decide the nature of the work that I do. I also get to decide what I personally need to do versus what I want to ignore or delegate to others.

Working at Microsoft I was given great freedom in how I chose to approach my job. However I still felt compelled to act a certain way in order to conform to the corporate structure. Despite the hefty salary and bonuses that I received I also felt limited in terms of how long it would take to climb the corporate ladder.

I’m also less motivated by financial gain now compared to when I graduated from college, and the opportunity to measure success in terms of “the quality of my lifestyle” is super exciting and motivating. This did not seem like a possibility in corporate-land.

As a result, I’m far more motivated to work and work hard running my own business than I was working for a large corporation.

3) Time management and discipline

Companies have their own rhythm and heart-beat. At Microsoft we had regular checkpoints when building new products or crafting new business plans. The over-arching fiscal and corporate calendar also drove a cadence for starting and finishing important projects. The never-ending presence of deadlines meant that even if I was very poor at time management, I still ended up getting things done.

It’s like I was in a river that was always moving, regardless of my own efforts.

Running my own business is totally different. Discipline and time management needs to come from within. Nobody’s getting on my case to deliver results. It’s up to me to figure out the best use of my time, to pick the right goals for my business and to deliver against those goals.

I’ve always considered myself a disciplined person. Running my own business has shown me how much opportunity I have to improve in this regard. If I don’t get things done there’s no one else to pick up the slack. I don’t have a boss to check in with me on how my project is going. There is no Senior VP or CEO relying on my work to reference in their next speech or board presentation.

4) Facing fears head on

Being my own boss has forced me to face my fears head on. I’m amazed at how I was able to get promoted consistently and succeed in my corporate job and still have deep-rooted fears around my own abilities to perform and be successful.

I’m now convinced that everyone has fears like this, particularly those who are successful in a particular type of job. The thing I’ve is that people – including me – have adapted strategies for succeeding that help them get around and compensate for whatever they are fearing deep down inside.

My fear was simple but insidious: the fear of not being good enough.

As an entrepreneur, this fear kept me from reaching out to my friends, my former business partners and even strangers to help build my business and get new clients. Since my business relies on referrals and working one-on-one with people, my fear was killing my business before it even started. I was afraid of being seen as “not a good coach” and “unsuccessful”.

Instead of reaching out to people to offer my coaching services or request referrals, I would spend all my waking time studying practicing my coaching skills and wasting time fiddling with my website and trying new internet marketing strategies for getting clients. I became an expert at doing everything but the one thing that really scared me which was reaching out to real human beings and offering my services.

When you run your own business it’s like a bright flashlight gets directed at all the dark corners of your personality that you’ve been able to ignore or dance around while working in a large team environment. As your own CEO, you no longer have this luxury. You need to face these fears and if they are holding you back from succeeding in your business, it’s up to you to do something about it.

Next I’ll explain exactly what I did to overcome my fear.

5) Asking for help

During much of my time at Microsoft I was a people manager. Most of the projects I worked on were also built around large virtual teams. There is something awesome about working with a team, particularly a high-performing one. A high performing team has regular conversations about what’s working what’s not working and how to overcome challenges. Team members are willing to help each other.

Running my own business there is no built-in structure or team to have these conversations with. If I’m missing a skill or I’m struggling with something it’s up to me to figure it out or ask for help. I’ve learned to get really good at asking for help!

It all started in May 2015, as my wife and I decided to settle down in Golden, CO (outside of Denver) and I found myself struggling to find new clients as my coaching business was getting off the ground. I was spending all my time doing everything but what I really needed to do, which was have conversations with real people who could either benefit from my service or refer me to someone. Instead, I was spending all my time running passive social media updates and trying learn more “skills” by taking coaching training classes.

I was letting my fear of “not being good enough” run my business!

My struggle got the point where I almost threw in the towel. I absolutely loved coaching but was hitting a wall with growing my business. Luckily I met someone who helped me face my fears and get over that.

This person’s name is Andrew, and he’s been coaching me for the past five months. He created and sold his own software company, and has coached execs and leaders for two decades. Without his support I would’ve given up and run back to the corporate world. I am certain of that!

My experience in working with Andrew is further validation on the power of coaching. Andrew asked me hard questions to help me get clear on my motivation for starting a business. He helped me focus on the things that are holding me back. Since working with my coach, my business has steadily grown and I’ve thoroughly enjoyed the process. I now see what is really possible in my business and lifestyle.

This doesn’t mean things are “easy”, but it does mean that I now know what it takes to make progress and face my fears.


I’m now 10 months (as of October 2015) into this journey of building my own business. Happily, I can say that I don’t regret leaving the comfort of working for large company. Wherever this new journey of being my own boss leads me I’ve already had enough learning to make it all worthwhile. It helps that revenues are growing and I now can see my new venture as not only personally satisfying and fulfilling but financially viable and affording me the lifestyle that I truly want.

Have you made the transition from corporate life to Entrepreneurship? What have you learned?  Let me know in the comments!

P.S.: Interested in learning how I can help you advance your career and build a high quality lifestyle?  Click here to apply for a free “Rapid Results” strategy session with me! During this conversation I can help you identify and work towards solving a big problem in your life or career. Apply today.

Published by Ravi Raman

Executive Coach + Yogi + Endurance Athlete

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