I remember the day I decided I was no longer going to be an employee. I had worked in startups my entire life and I felt like every time I would start a new job it was one more time I was missing the boat – the boat on which I was, once again, not the captain (cue images of Gilligan’s Isle right after the shipwreck).

Business ownership seemed, to me, to be the ultimate adventure, and the only way to really be completely satisfied with the results of your efforts. Sure, I could do well on my assignments at work, or we could have a big win as a team, but at the end of the day I was still going home empty-handed. The results didn’t mean as much as they could.

So, within a month or two I had taken out a loan for the equivalent of a small country’s GDP (or so it seemed at the time), quit my job and bought my ticket on the Entrepreneur Express. And everything was smooth sailing after that – we made lots of money and had gobs of success and now I use dollar bills as packing paper when I send my $1M watches to get serviced.

Hahahahaha! I just laughed so loud I woke up my kids (they had to get up for school anyway).

OK, look. The first part is true. I dove in without a second thought when an opportunity presented itself. Here’s the rest of the story: I was 7 months pregnant with my first child, in the process of renovating our home, still in debt from student loans, playing landlord to my tenant in the city, and I had exactly no contingency plan, or plan in general.

To say the next few months – heck, the next few years – were easy is like saying that Tiffany just gets by making jewellry (I’m redesigning my site right now to be Tiffany blue – it’s on my mind).

Dear reader, it was really, really tough.

While we did pretty well building our business and grew it into a respectable boutique consulting agency, all the things that it took from me to do so, while contributing to my household and being something more than a deadbeat mom, and keeping our financials afloat, and and and…. it nearly killed me. I never caught up, financially, and ended up handing my business back to my partner after 8 years with no winfall and no great claim to stake for all my efforts.

Was it worth it? Absolutely – I learned SO much that allowed me to do it right the next time, and the next time after that, and to transition into a coach for others who were going through the same thing.

Would I recommend this approach? Nope. Not in a million years.

I had no Turning Point.

I had not given thought to the implications of diving in head first. Nor had I planned for what would happen if I did. I had no financial analysis or considerations for how this would impact my health, my family, or what I would need to have in place to be able to support this lifestyle.

Now, had I given this some serious thought, and mapped out a plan for when I might be comfortable or able to transition into a full time business owner, it might have impacted my outcomes significantly. Sure, I may have had to wait for a little while longer before I became a business owner, but the outcomes, I think, would have been very different.

[bctt tweet=”To successfully transition from your 9-to-5 job, you need to know your Turning Point.”]

You need to know what life looks like at that point in time that you feel ready to transition into entrepreneurship full time. Your Turning Point will look different to mine, and different to the nice old lady next door selling Tupperware, and different to the 18-year-old self-taught web developer hacking away in his parents’ basement.

Your Turning Point should include considerations from the four pillars of a business owner’s transition – Financial, Operational, Personal and Your Job. When you’ve mapped all of these out, you can look at this plan as a guide post to fulfilling your dream. You’ll learn more about the Four Pillars Plan in my 9-to-5 Transition Plan Workbook.

Without a plan, you’ll continue bobbing along in the life raft, waiting for Ginger to bring you an oar. So, get out your pen and paper and start brainstorming what your Turning Point is. Better still, download my free 9-to-5 Transition Plan Workbook, which will walk you through creating a plan of your own.

Tell me in the comments…

What does your turning point look like? When will you know that you’re ready to fly free?