In 2011, I said goodbye to both the stress and stability of my 9-to-5 when I quit my corporate career of 18 years. Inspired by the freedom and excitement of the entrepreneur lifestyle and truly needing a change for my personal wellbeing, I was ready to jump right into starting my own business. However, I was so eager to begin and confident in my abilities that I overlooked some essential questions. Questions that, had I asked them, would have helped my marriage and my finances.


Well, the good news is, my marriage survived! But, would I want you to have the conversations that I had? No way. As they say, hindsight is 20/20, and I am putting my clear vision to work to share my journey, my lessons, my hindsight—so that you don’t have to figure it all out for yourself.


What is the first tough lesson I learned after setting out on my own? Your success in corporate is not immediately transferable. I spent 18 years in the corporate world and built a rewarding career, even successfully running small startups with the ecosystem of the larger corporation. My corporate role built my passion and wealth of knowledge for my entrepreneurial endeavours, but it did not prepare me for the uphill climb at the start.


Even the great Michael Jordan experienced this lesson when he switched from one sport to another. Being one of the best basketball players ever didn’t immediately translate into being an amazing baseball player. He had to start in the Minor Leagues and work his way up, except in his case he couldn’t progress at a rate that was good enough for him so he quit and went back to basketball.


Your success in corporate is not immediately transferable. Click To Tweet


In your case, the last thing I want you to do—and likely the last thing you want to do—is to quit your own business and go back to corporate. Instead, take some time, think it through, and make a plan. These 8 questions, based on my firsthand experience and what I have learnt from coaching hundreds of other corporate escapees, will better prepare you to take your success in corporate to the entrepreneur world.


  1. Do I have a 12-month runway of savings?

– It will take you 2-4 times longer than what you think it will take to earn a wage. You might be the 1% who creates a positive cash flow faster, but you can’t count on that being the case. When it comes to the financial livelihood of you, your family, and your business it is so much safer to underpromise and overdeliver.


  1. Do I have funds to start my company?

– Depending on what kind of company you’re starting, at least $50,000 will be necessary to cover the essentials. Just starting out you will need accountants for taxes and business setup, lawyers for business registration and drafting any contract documents, web developers to build your website, designers to create your website design and any logos or marketing materials, a coach to guide you through the things you don’t have experience with, and in some cases qualifications to legally provide a certain service. Remember from question 1, it is always safer to underpromise and overdeliver, so having funds to start your company gives you room to breathe assuming you don’t get client revenue in the first 12 months.


It is always safer to underpromise and overdeliver. Click To Tweet


  1. Am I aligned with my partner and children?

– Is your partner and/or your children counting on a certain lifestyle being sustained? What have you promised your life partner for a monthly contribution to? When you start your business, you will possibly have to trim non-essential expenses that will affect your family. If you often go on overseas family holidays, eat takeaway often, or buy a lot of presents, that may change as your finances fluctuate in the transition away from a corporate salary.


  1. Do I have the right company structure in place?

– Choosing the right structure can protect your private assets if things go pear-shaped. This is where consulting with a lawyer or even a business coach can assist you a great deal. It is much easier to set everything up right from the start than it is to dig yourself out of a hole if you should find yourself in one. Some options include protecting yourself by putting assets in your life partner’s name, getting insurance for your business, or getting professional indemnity insurance.


  1. Do I have enough credit cards and variety in my credit background?

– As soon as you start your own business, banks will look at you differently than before. Self-employed people typically end up well down the list when getting considered for credit cards, loans, or anything where proof of income is considered. Especially starting out when your company has no history to show that you will make money, it may be challenging when applying for new credit.


  1. Do I have some mentors who have gone before me?

– Join a community of like-minded people who can help you reduce the mistakes you are bound to make! You will make mistakes, but you don’t want to make too many and a lot can be avoided just by learning from others. Also, running your own business can be very lonely, which makes the hard days feel even harder. Having a like-minded tribe to support you in those times is more important than you can imagine.


  1. Do I have some friends who will ‘throw me a bone’?

– My first paid clients were close friends who had problems I could solve. This helped with cash flow until I worked out what I really wanted to do and how to market to that. Your ideal client will evolve with time, but serving people you already know is a great place to start.


  1. What is my Plan B?

– If your business doesn’t work out as you planned, what do you want to do in 12 months? Having a backup plan creates a safety net that takes the pressure off of you to succeed—it is nice to know it’s there, but let’s hope you never need to use it. It is best to have this conversation up front so that if you do need to go to Plan B, you won’t be caught up in the emotion of failing when trying to figure out what to do.


Whether you are still working through these questions or you’re already hard at work on your new business, consider a community like Build Live Give to take the pressure off you. There are hundreds of other corporate escapees out there going through the same things as you. Build Live Give provides a community connection along with a laundry list of valuable resources and vendors vetted by my years in business. So, connect with me… I would love to hear your personal experiences as a fellow corporate escapee.