How to know when to stay the course

Cassie Widders
5 min readNov 2, 2022

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When I was at school, I was given a choice of 8 subjects of which I could choose 3 to study for GCSE. We were a small school in rural North West Wales, and in my arrogant teenage phase, all I saw around me were limitations.

Limitations on what I could study. For a language, there was only the option of French. For studying abroad, there was no money for me to do it. For my future, I felt hemmed into the shrinking Welsh culture, part of me so proud that we were continuing to speak Welsh as our primary language and keep it and our identity alive, another part suffocated by the small pockets of places I could therefore live if I wanted to continue to hold that baton.

When I entered the workplace, my excitement at climbing the ladder and earning my own money quickly morphed into the same feeling of restriction I had previously felt. No, you can’t apply for that promotion, you haven’t been here long enough…That’s a great idea, but just stick to this and maybe you can explore that project another time.

So starting my own business, I have come to realise over the years, was a way for me to experience the unlimited. Now I’m not talking about the ever-glamourised you can earn whatever you want and work 2 hours a day kind of unlimited. It was just the ability to work on what I wanted to work on, in a way that I wanted to work. Like this morning, I am writing this piece, a piece I wanted to write, in the environment I chose, at the time I chose to write it.

But in my goal of breaking down the limitations I had always felt, the absence of those limitations has opened up infinite choice.

Infinite choice is a privilege, I recognise that. And it is far better than a lack of choice. But it is also a catalyst for restlessness, for dissatisfaction, and for distraction.

We as human being are naturally curious creatures, and if you start your own business, you often have an ambition or vision you want to achieve. Add all this together and it leads to a struggle of knowing when to stay the course, and when to shake things up.

I found myself at this very point recently. Studying to become a digital wellbeing coach was initially something to complement and formalise the work I currently do. But now, my mind is whirling with new ideas and possibilities and directions.

It’s also a combination of ‘I’m my own boss, I can do what I like’, slight boredom with the repetition demanded when creating my content, and a buzz of excitment at embraking on something new. I think we’ve all been here at some point in our lives!

All these choices and opportunities, and no one to narrow the path for me.

So what did I do? How did I know whether to stay the course, or to change?

  • The first thing I did was to go back to my definiton of success.

What do I really want? I worked backwards. I started with my vision of the lifestyle I wanted, and then how the business I was building would facilitate that lifestyle. I visualised and thought hard about what would give me purpose, and what I value in life.

If you struggle with that, start by just throwing a few words out there that mean something to you, and imagine a vision based on those things being in your life.

  • Secondly, I spoke to people. Lots of people.

You could hire a mentor or coach, but I wasn’t in the financial place to do that. I also feel it’s beneficial to get a lot of people’s advice on this. Trusted people (friends, family), people with exertise in what you’re doing/considering (this usually involves a fee as it can be a service, but if you have people like this as friends who are willing to chat informally, or if you can offer a service exchange, it may work out), and people with an understanding of what you’re going through (for me, that’s online business owners who get it).

Get their advice on your thoughts. Even just talking out loud and having someone listen may help you strategise.

But don’t forget to get the advice of your audience. Create a poll on LinkedIn or Stories, ask for DM or Zoom conversations, or even create larger surveys to truly understand what they need, perceive and feel about you and this shift.

  • Thirdly, acknowledge the hard truth that life isn’t a fairytale.

There are times when we just have to do things we don’t want to do. Even living on the tropical island of Borneo, I still have to go food shopping and do the dishes!

Life and business will be mundane at times. And sometimes we have to work when we don’t want to work, and work on things we don’t want to work on.

Something I actually love doing, I can not want to do from time to time.

This does not mean I’ve fallen out of love with my business! Unless it’s a long term feeling, simply acknowledging that this happens and understand that it happens to us all is a big part of achieving contentment on this entrepreneurial journey.

  • Finally, use my SET method of weaving all of those things into this formula:

Strengths: Do I have the strengths/skills to create/ implement this? Can I learn or can I outsource? Are these skills going to be enough to build the vision I have?

Enjoyment: Would I enjoy this shift and all it encompasses in the long term? Would it contribute to my definition of success?

Time: Do I have the time to create/ implement this change right now? Can I make time or can I outsource? Can this be something for the future? Will this shift impact the time I spend on my business in a way that feels good to me and in a way that is actually possible/realistic?

We can dream and have big visions and goals. We can get shiny object syndrome and distracted by new opportunities and options. There is nothing wrong with this. In fact, it’s healthy as it shows a hunger for life and what you’re creating.

But we also need to be realistic. We need to ensure that what we’re doing in our business keeps it here in 5 or 10 years time (in some form). And we need to ensure that what we’re doing is going to pay the bills.

This is what my SET method does. It ensures the sustainable success of the business.

Thinking all these things through helped me understand that my infinite choice can also mean limitations, but that those limitations can actually facilitate choice. The irony! By using these prompts and questions, I was narrowing my path which helped me choose!

So with all those things, I hope this helps you, as it helped me, determine whether or not to stay the course.

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Cassie Widders

Social Media Strategist, Podcast Host, Speaker & Digital Wellbeing Advocate