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.

  • What are your business values?
  • What are your long-term plans?
  • Take a few minutes to check if your future plans are aligned with your business goals and values. If not, what needs to change?
  • What are your business offerings? Are they in line with your mission? If not, what can you do to adjust them?
  • Do a skills inventory. Is there anything missing? What are some ways you can continue investing in yourself and improving your skills to help you reach your goals?

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.

  • Looking back at the past year, what are you most proud of?
  • What goals did you meet this year?
  • What goals did you miss this year? What prevented you from reaching your goals?
  • Where are you feeling stuck? What role does fear play in that?
  • When you think about the different experiences you’ve had this year, what are the most important lessons you’ve learned?

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.

  • Consider how you spend your time each day and the ROI of each action—is there an area where you’re spending too much time and energy for the amount of return you’re receiving? If so, what can you do to adjust it?
  • Analyze a typical week. Are you satisfied with your time management? Are you staying in your zone of genius? Could you benefit from partnerships or working with contractors? What does your ideal week look like?
  • How well are you taking care of your body, mind and soul? How can you be kinder to yourself?
  • What is one habit you want to develop this year? What can you do to get started and make it a reality?
  • When you have a big win, what do you do to celebrate? Take a look at a few of your wins from the past year and if you haven’t yet, make a plan to acknowledge and revel in your success.

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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