How Do I Know If I’m Making The Right Choice?

“If you don’t risk anything, you risk even more.” – Erica Jong

For a lot of career changers and new entrepreneurs, the biggest question in their mind is “How do I know if I’m making the right choice?” The short answer is “You don’t/won’t know” But that’s honestly okay and shouldn’t turn you off – Because staying stuck is the riskiest plan of all!

Starting your own company or networking your way into a new career is not an irreversible move or (just one) decision – Everything is a test and you can always change your mind (AND use your old profession as a cash cow whilst planning your next plan of attack). But if you don’t make a choice, you’ll never know! That’s the beauty of actually making a choice and why it’s okay not to know everything for sure up front. Though there are plenty of ways to get pretty close to knowing.

 The Dating/Love Analogy (and why it’s so relevant)

During my talks and workshops when asked the “How do I know?” question, I always use the analogy of dating and falling in love. How do you know if you’ll love someone and if you’ll live happily ever after? Well, you would definitely want to start by going on actual dates and spending time with the person to find out.  Over a (shorter or longer depending on your preference) period of time you get to know the person better and experience how they make you feel and who you become in their presence. Then, if things are really good and you allow yourself to fall in love, you might move in together or even get married.

Do you know if you are making the right choice by dating, by moving in together or even by getting married? No, you don’t! But you still do it because you are willing to take a chance on something potentially mind-blowingly amazing in return for something that requires a full commitment.

If we were all over-thinking and not physically engaging with the falling in love question, the world would be an unbearably sad place to live in. So why are we doing it with something that takes up just as much of our time?! Do you see where I’m going with this?

 Start test driving (dating) your choice!

You can’t think or rationalize your way through to a career change or business start-up decision – You need to start “dating it” – Feeling with your own body/mind and through lived experiences and interactions what it’s like when you use certain skills, interact with certain people or solve specific problems. In “Rikke World”, I don’t call it dating – I call it “test driving.” The sooner you start putting on a small workshop or event for the company you want to start and the earlier you join that evening class or meet-up group to learn about the subject of your new career etc, the faster you’ll get to the stage when you are ready to make the jump because you will have real life and market feedback to base your decision on. Even though you won’t know 100% for sure it’s the right choice, you’ve had enough consistent, personal feedback over a sustained period of time to feel pretty damn sure!

What you’ve personally experienced and lived through as making you feel amazing AND able to be unapologetically yourself (just like true love;) is the closest you’ll ever get to an iron clad guarantee in this new world of work. And worth making the jump for. 

Remember, everything is a test and you can always change your mind or course correct. That surely beats staying stuck in a soul-destroying job with a predictable outcome any day!


 My challenge to you:

So here’s my challenge to you – Rather than asking “How do I know if I’m making the right choice?” – I suggest that you ask yourself – “What actions can I consistently take to get more real life/market feedback to help test drive my assumptions and ideas?” And for some of you (you know who you are!) who have been at this for a while, the question might be “Do I risk more by not jumping?” Remember, just like with relationships you can always move out or get divorced – Noting apart from death is irreversible. And please live before you die.

If you enjoyed this post, then please share it with two people you think need help with making a decision – Thank you!

On Career Change, Own Business, Self Employment

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