Questions to help you reflect and plan for 2020

by Robyn Roste

There are all sorts of positive reasons to spend time reflecting on your business, asking questions and planning.

Things like reducing anxiety, improving clarity and encouraging creativity. But making the time to work on your business instead of in your business? Sometimes more difficult than it seems.

A while back I purchased a self-paced digital course and one of the first tasks was to film a three-minute video outlining things like why I was taking the course, where I was at in my freelance business and tasks I was struggling with.

My first instinct was to skip the video and jump into the actual coursework but I did end up quickly recording something and moving on.

The other day I was cleaning up some digital files and ran across the video so I stopped and watched it. Even though I felt like I hadn’t made as much progress as I had wanted to from the course, once I saw the video I realized I have come a long way. I felt encouraged and motivated to keep going—things I wouldn’t have felt if I hadn’t taken those three minutes to talk about where I was at and where I wanted to go.

If this seems like the kind of thing your freelance business could benefit from, here are some prompts to help you reflect and plan.

Admit where you’re at in your business and dream about where you want to go.

It’s easy to look at other freelancers and think that your business needs to look like theirs in order to be successful. But even if other freelancers look like they know what their next steps should be and always seem to be going in the right direction, the truth is no one knows what they’re doing.

A big part of entrepreneurship is making it up as you go and figuring out your own path. Instead of wasting time worrying about what others are doing or comparing your business to others’, why not spend time evaluating where you’re at and dreaming about where you want to go?

Here are some prompts to get you into that headspace.

Keep record of your successes and failures and reflect on what worked and what didn’t.

Whether or not you keep a formal journal or just create space to do big-picture thinking, take time to review your successes and failures from the past year. While it’s important to acknowledge the wins, it’s also smart to face the not-so-great moments and consider what you can learn from them.

This can be as simple or in-depth as you like. Take these questions as a launching point for running your own SWOT analysis (strengths, weaknesses, opportunities, threats). Make a plan to do more of what worked and less of what didn’t in the future.

Take some time to reflect on your work/life integration and how you can pursue excellence and success while still having a life.

While we love our freelance work and don’t mind spending extra time on passion projects, sometimes our work can take over and send us spiralling towards burnout. It’s important to be self-aware and set boundaries on our time in order to stay healthy and balanced. Here are a few questions to prompt inner reflection and help you make positive changes.

For me and my business, a big part of moving forward is looking back at where I’ve come from. I have an amazing ability to forget about all of my progress and focus on how far I have to go to reach my goals.

In order to dissuade discouragement I’m learning to take a step back from the hustle and consider where I’m at, where I want my business to grow and then break it down into manageable steps for how I’d like to get there.


Robyn Roste is a freelance writer in Abbotsford BC who uses her journalism training to help others share their stories. Her blog was recently listed in The 100 Best Websites for Writers in 2020 by The Write Life.

Posted on January 14, 2020 at 8:31 pm by editor · · Tagged with: , , ,

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