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Going All In On the Family Biz: If I Knew Then What I Know Now…

If I knew then what I know now, I may have hesitated for a little while longer…

I may have decided to wait – to take more time to top up our emergency savings account, to really figure out our five-year plan.

The last two years haven’t been easy. There have been months when we struggled to pay all of the bills. Weeks when our work would come before our marriage. Days when we questioned whether we made the right choice.

But if there’s one lesson I’ve learned over the last few years, it’s that goals and plans are merely a guideline. While they certainly serve their purpose, it’s rare that all of the boxes get checked, that all of the steps fall gently into place.

Making big life decisions is hard. And when you tend to overthink everything (like I do), they weigh heavily upon your shoulders.

But I’ve learned quickly that action is better than inaction. It’s better to take a step in the wrong direction than to not move at all. It’s better to learn and grow from your mistakes than to miss out on an opportunity you never knew was there.

The truth is: You aren’t supposed to have it all figured out.

You aren’t supposed to know exactly when the right time is.

You aren’t supposed to know exactly what the results will be.

You aren’t supposed to know where the path will lead you, and how it will all turn out in the end…

All you can do is focus on the elements within your control.

Do your research, talk to others who have been through similar experiences. Don’t be afraid to ask for advice.

And in the end, listen to your gut. Your intuition often knows where you need to be before your brain does; you just have to slow down long enough to pay attention to it.

Two years ago, Luke and I made the decision to go all in on the family biz.

If I knew then what I know now, I’d tell those two kids sitting at the kitchen table in front of their Excel budget and list of pros and cons that it’s all going to be okay.

You are going to figure this out.

You are going to make it work, and it’s going to be a great success.

You’re going to face some major challenges, but each one is an opportunity to prove you are willing to do whatever it takes.

You’re going to have to put new boundaries in place, while also gaining a sense of freedom you never knew was possible.

You’re going to learn things about one another that you hadn’t yet discovered, even after nearly a decade of being together.

You’re going to experience growing pains, and many stressful days, but you get to do it together.

If I knew then what I know now, I’d tell myself: you’re making the right choice.

One day you’re going to sit back and reflect on how far you’ve come, and realize it was all worth it.


Charlotte Ottaway

Charlotte is the founder of Web of Words. She helps solopreneurs and small business owners create real human connections online through blogging and social media. Her work has been published in Maclean's, Canadian Business, Zoomer, The Globe and Mail, The Huffington Post Canada and other Canadian publications. Better known by family and friends as Carly, she currently resides in Newmarket with her husband and fur-babe. To learn more, check out her portfolio at charlotteottaway.com and follow her on Twitter @charlottaway.