Usually I bring in the New Year with a glass of champagne while dancing at a house party. It feels like the most appropriate way to celebrate another year gone by. You sweat out the challenges from the previous year and invite new opportunities to make dreams happen. You wake up the next morning hungover, grab some greasy food, and start what should be the best year of your life.

But this year was different.

I travelled a little bit more than usual this holiday season and ended up catching a cold. Not the cute sneeze here or there kinda cold. This was a hacking cough, runny nose, “will you make me chicken soup” kinda cold. So for the first year since high school, I stayed in on New Years Eve.

I had more than enough time to watch the ball drop, read 100 pages in my new favorite young adult fiction series,, AND start my annual planning session for 2016.

Now planning is perhaps the most important part of my life as a creative entrepreneur. I come up with 3-4 new business ideas every week and have my hands in quite a few different projects, so its incredibly important for me to map out a plan to make these visions into reality.

Ideas are meaningless without action.

I’ve developed a process that is surprisingly straight-forward. It’s also pretty practical. You set intentions and then plot out what it takes to make that intention a reality.

1. Clarify the big picture and find your intentions.

First I like to look back at the previous year and define what were my successes and what were my failures. This tends to be a combination of work and personal goals, but I like to think from the highest top level.

What did I enjoy?

What made me feel the most proud?

Where did you drop the ball?

When were you the most afraid?

What did you do to find inspiration?

What experiences did you learn from?

How did you balance work and personal life? What could you do better?

If you’re a freelancer, plot out your revenue month to month and the clients you worked with.

After answering these questions, I had a pretty good idea of where I want to go with my next year. I call this setting an intention. As in, “I intend to…”

Intentions are like goals, but they speak to higher aims. Goals are meant to be specific, while intentions make sure that we ground ourselves in principles despite where our career takes us.

My intentions:

  1. I genuinely value work/life balance and intend to make space for enjoying everything that life has to offer. For me that means being available to work 6 days a week, but also making time throughout the day, every day to recharge and do the things that make my household run better, like errands, grocery shopping and appointments.
  2. Traveling out of the country for the first time was one of the best parts of my year. I intend to visit new places regularly, so I can feel inspired.
  3. One of my biggest challenges last year was feeling overwhelmed by the amount of client work that I took on. While I was proud to have the opportunity, I intend to work with happy clients that respect my talent. This is non-negotiable moving forward.
  4. I want to foster stronger relationships with my partner, family and friends and overall could do a much better job of communicating regularly. I intend to make facetime calls, send letters, and make friend dates a priority in 2016.
  5. I intend to make location independence a priority, so that travel can always be a part of my work. For me this means creating passive income streams and moving more of my business online.

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2. Find 4-6 big projects that you’d like to take on. Then map out your overarching goals of the year.

Regardless of if you work for yourself or for a company it’s very easy to find the 4-6 big projects that you’d like to take on for the year. These can also be personal or professional, but they should be things that directly align with the intentions that you’ve outlaid for yourself. They also should be things that you genuinely want to achieve in 2016. Be as realistic as possible, but don’t be afraid to have one or two goals that push you outside of your comfort zone. That way when you succeed, you will have stretched your capacity.

5 Big Projects for 2016

  1. Productizing my service based business. One of my major goals is working to create better systems for my graphic and web design business, so I can better plan my revenue. Specifically, I am aiming to make $8500 per month.
  2. Plan and execute the second annual VenturePOP Conference. The first year of the conference was incredible and I want to build on that momentum with an engaged audience, amazing speakers, and a beautiful new venue.
  3. Find speaking engagements. In 2016, a few speaking engagements found me. I want to be much more proactive in finding opportunities that match my brand and goals.
  4. Make writing and illustration a priority. I’ve decided that I want to work on developing my skills by consistently creating content for all of my businesses ventures.
  5. Launch Curious Tribe, a subscription based digital magazine for creative entrepreneurs. Publishing is genuinely my passion and I want to build a platform for tangible next steps for creatives and their business growth. This is probably the biggest and most daunting of the goals, but in conjunction with VenturePOP, it is the most exciting.


3. Plot out a month by month list of objectives and tactics that will make your dreams happen.

I suggest only planning for the first 4 months of the year (January-April), then revisiting this document in the beginning of April to readjust. I tend to do my planning on a quarterly basis, because it allows space for you to reprioritize and forces you to think on a granular level on what it takes to push the needle forward on your goals.

This will be an extremely long list of things to do because it will include all of the baby steps that it takes to make that goal a reality.

Your objectives paint the picture of what your completed task looks like.

Your tactics are the specific group of tasks that you need to complete in order for the objective to be completed.

Here’s a brief example:

Objective: Launch new packages for Creative Lab.


  1. Write a list of 5-6 potential packages
  2. Define the specific delieverables and map out the process for each of the packages
  3. Create icons that represent each of the packages
  4. Compile this information into a beautifully designed PDF
  5. Design a landing page for each of the packages
  6. Write a 1000 word ebook that promotes each of the packages.
  7. Compile this information into a beautifully designed PDF for each ebook
  8. Create a landing page for the ebooks
  9. Create separate page for each of the ebooks
  10. Create Pinterest graphics for each ebook.
  11. Schedule posting of each of the ebook graphics to Pinterest using Bufferapp.
  12. Promote the individual services pages through Facebook and Twitter scheduling on Bufferapp.
  13. Promote the individual ebooks through Facebook and Twitter scheduling on Bufferapp.

4. Do the Work

This I actually the hardest part. You’ve set your intentions, made some goals, and gotten down to specific objectives and tactics. But the only way to actually make your dreams a reality is to do the work you’ve laid out for yourself. This requires a dedicated resolve and a good to-do list.

I’m personally subscribed to TeuxDeux, an online To-do list that helps you assign tasks for the day. What I love about the system is that whatever you don’t complete gets pushed to the next day. This helps make sure that nothing ever really falls off your list.

While I like that system, for me the easiest way is to print out the master do list in a big 16 pt font (2 columns) and staple it together. Then every day, I make it my mission to knock 5-7 things off the list. I currently use this simple notebook for day-to-day planning. If I finish all of the tasks for the day, I usually reward myself by leaving work early.

At the beginning it will feel impossible, but as you complete the tasks, you mark them off on your printed master list as well. Every week as you see the tasks disappear you will feel inspired to put in more work to make your visions a reality.

What are you planning to accomplish this year. Let us know in the super secret Create & Conquer Facebook group.



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