My decision to change my career and start my own business was huge, but it was something I had always wanted to do and was passionate about. In those initial months, the words “You will fail” did often play in mind, on repeat, like a bad 80’s song. However, in leveraging the skills and knowledge that I had developed in my former career, plus learning from my support network, I was able to navigate my way to a solid first year plus reflect on the key Lessons that got me there!


Lesson 1: Fear will not pay the bills

In the first couple of months, the fear of failure was intense. It often kept me up at night and consumed many of my thoughts and conversations. It is hard to focus when your subconscious is playing out a horror movie for an audience of one.

While most people were supportive; I placed more weight on the people who told me how many businesses failed at the start-up stage.

However, fear does not pay the bills (or grow a business). To overcome this, I faced that fear by scenario planning potential areas of failure or weakness and rationally considering the probability of each failure occurring. Then logically create a contingency for each.


Once I had faced my fear in a rational way, my mind went from a state of worrying to strategising.


Lesson 2: Visualise success


When you start out, it is hard to see the forest for the trees. That is where a vision is critical. It must be something that you believe in. Something that will drive you through the tough times and remind you of why you started in the first place.

A vision does not have to be complicated, consider these core elements when building one…

  •  Define what is the core outcome or benefit that people will derive from your business
  • What is your businesses unique selling point
  • Who is your business targeting?

Use this information to create a short, simple, clear and ambitious vision (one sentence if possible) that is unique to your business and aligns with your businesses values.

I brought my vision to life through a vision board for the next 12 months and from this a 3-year plan with the major focus areas and objectives.


Lesson 3: Create a plan 

A vision without a plan is a dream. Our team converted our vision into a three-year strategy. Which we reversed engineered to work out milestones and targets for each year. We kept ourselves accountable by meeting every 60 days to determine the key deliverables for the next 60 days. We also take a day out every six months to review our 3-year strategic plan and make course corrections.

 Lesson 4: You will make mistakes 

If you truly want to succeed you will make mistakes in the game called life. You will (occasionally) fall flat on your face.

My mistakes came early. For example, I paid a lot of money to have my logo and website professional designed and built. Looking back on it, I did not love the result, but given my bias for action, I launched with it. It was not till some months later that a trusted advisor told me my logo and website were not fit for my business!

I was gutted. Then I reflected on the advice, reassessed and rebuilt it with help from people I trusted.


Lesson 5: Find trusted advisors 

When I was a graduate, I had an incredible mentor, who told me that in life and business you need a board of advisors. Like how a company has a board of directors. Each person’s role is to give you a different perspective or bring a skill set to the business that you may not possess.

When I started my business, I thought I could fly solo, but I realised I could not! So, I ended up asking those around me for help. From my amazing wife who brings a thorough understanding of project management, through to accountants and other business owners. All of whom have challenged me and guided my decision making based on their knowledge and skill sets. The key is to find people who will tell you what you need to hear, not what you want to hear.


Lesson 6: Outsource your weaknesses


I am confident of my strengths and over the past year have also become more intimately acquainted with my weaknesses. When it comes to administrative tasks, I tend to procrastinate. Which means that jobs that are essential to running my business pile up, get missed and cause me anxiety. Also, time spent on this means less time focussing on my clients and building my business.

So, I decided early on to hire an assistant (check out Vicki is the backbone of the business. She describes it like this, “You are the guy on stage, and I am the manager that makes sure everything else runs to plan”.

With Vicki’s support, it also frees up time to spend with my son and my wife.


Lesson 7: Take calculated risks 

When I started out, it seemed everyone had the perfect solution to grow my business by x10. All I had to do was sign up to some expensive course, web program or software package.

It was tempting to place all my bets on black. Instead, I decided to take small, calculated risks. For example, instead of paying upfront for services, I used trials to see what worked and what didn’t. With a finite budget and time, you need to determine where you will get your best bang for buck.


Lesson 8: Just because you are alone doesn’t mean you are lonely


Having to leave my fantastic team in corporate was hard. On top of that, embarking on a new career initially felt like I was starting from ground zero. I found that by joining relevant associations, in my case International Coaching Federations Victorian Chapter and meeting other Coaches, gave me a great sense of belonging.

Reflecting on and writing about my experiences and publishing them on social media has also meant that I have connected with a raft of interesting and knowledgeable people plus received helpful feedback which has contributed to growing my business.


Where to from here?

My first year was amazing, scary, exciting and nerve-racking, and I cannot wait for an even better year ahead.

If you have any tips or lessons for people starting out, I would love to hear them. Either email me or leave them in the comments.

About the Author – Rajiv Jayarajah is the Founder of Bare Inc, a consulting and professional coaching firm specialising in creating clarity for business owners and leaders so that they can achieve their goals faster. It’s easy to connect, find me on LinkedIn, Instagram @bare_coach or

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