Two-Year Plans to Chart Your Career as an Entertainer

In For Entertainers & Performers by jcsum1 Comment

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Most self-improvement gurus and life coaches stress the importance of setting a long term goal or a dream. Some even go as far as asking you think what you would like people to say about you at your retirement party (assuming you have one).

While it is important to have a “dream” or long term goal, a long term goal is not particularly effective in creating strategies or tactics in developing your career.

This is because of the speed that the world changes today due to advancements in technology, economic market volatility and geo-political issues.

Setting short-to-mid term goals is a practical and effective way to grow your career as a performing artiste & entertainer, regardless of the level you are at.

Short-to-mid term goals are psychologically more attainable because you are not trying to reach an abstract dream like “be a multi-millionaire” or “headline in your own show in a casino”. You will also find it easier to achieve your long-term goal in incremental progressive steps rather than make one giant leap.

Two Year Plans

I recommend setting a short-mid term goal that is to be reached in two years. The goal must be specific and within reach, but should not be without challenge. The goal is designed to push and motivate you to work smart and hard towards a specific objective.

You should also set milestones at every 6-month interval as benchmarks to ensure you are on track to reach goal.

These milestones are important events in the timeline to ensure you are on course.

With the goal and milestones in place, you will create a plan that involves an overall master plan or strategy as well as the tactics used to execute your strategy.

Let’s look at the following example for an entertainer:

Two-year Goal: To increase your yearly income by 50%.

Your strategy to achieve this goal is to increase your show fee by 20% and increase the amount of shows booked by 20%. At the same time, you will reduce your expenses by 20%.

Your tactics to increase your show fee and number of shows booked may include:

  • Adding new & different material to the show
  • Increasing the scale of the show, Adding new costumes
  • Creating a new set of digital promotional materials to reflect the increased value in the show
  • Executing an aggressive email marketing & social media campaign to promote the new show

Your tactics to reduce your expenses may include:

  • Cutting down on unnecessary expenses
  • Reducing luxury expenses or hobbies
  • Reducing business costs where applicable. For example, moving to a smaller office to reduce rent, reducing mobile plans or website hosting plans that exceeds your needs.

The above may seem like a lot to accomplish but that is why you will not do everything all at once. Some tactics can be executed immediately while others require time. That is where the 6-month milestones come in. You will plan to reach your goal in incremental steps so that you will eventually reach the desired goal at the end of two years.

Your tactics may also change along the way as you will change your tactics re-actively if they do not seem to be working, if market conditions change or if new opportunities arise.

At each milestone, you should review your original goal, strategy and tactics to ensure that you are on course. If you have strayed too far off course, you need to tweak your tactics or strategy so that you steer back on course. If you are still far off from your goal, you may need to change tactics or work harder or smarter.

This is similar to rebalancing an investment portfolio every year to ensure your diversification and weight is in line with your investment goals.

After the two years come to a close, you must review to see if you achieved your goal. Or, if you did not, how far you were from it. It will then be time to think about and chart out another two year plan with your next short-to-mid term milestones in mind.

The process then repeats itself over the course of your career till you reach your long-term goal or retire.

This two-year plan process will help you grow your career and achieve your long term goal or dream in a systematic and focused manner.


If you are looking for a guide for your career as a live entertainer, check out my book “The Showbiz Master Plan” that is a live entertainer’s blueprint to creating a money-generating brand, making a consistent 6-figure income and setting up for retirement. It also includes a whole chapter on how to price and negotiate Big Money shows.

The Showbiz Master Plan Cover


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