Do you have a really challenging goal you want to accomplish either in your career or personal life? If so, I want to help you by sharing a story and putting you on to some reading I know will help you.

I coached an outstanding associate who, at the time, was eligible for promotion to partner in three years. He was with an entrepreneurial law firm, so he was be expected to be bringing in business by that time. I asked him:

I want you to honestly answer this for me, ok? Assuming you make your very best effort, do you honestly believe that you can bring in $500,000 in business in the year  you will be considered for promotion? Be honest with me.

He answered: Yes.

I then asked him to share with me what it will feel like to have succeeded in attracting $500,000 in business in 2017. Yes, this is the year we set out with the three year goal.

Then, I asked him to share with me, the first obstacle he sees to achieving that goal. Then, I told him to share with me something else positive about successfully attracting $500,000 in business. Then, I asked for the second obstacle he saw to achieving that goal.

I was using an approach called “Contrasting.”  This process can be both motivational and helpful in that it forces you to face the reality and be prepared for the challenges you will face.

I first learned of this approach reading Dr. Heidi Grant Halvorson’s book Succeed: How We Can Reach Our Goals. I recommend the book. She also discussed the idea in this Psychology Today article: The Motivational One-Two Punch for Overcoming Bad Habits. In the article, she says:

Daydreaming about how great it will be to land that job can be a lot of fun, but it won’t get you anywhere. Mental contrasting turns wishes and daydreams into reality, by bringing into focus what you will need to do to make it happen.

After going through the contrasting process, I asked the lawyer to set up intermediate goals working backwards. To get to $500,000 in 2017, what did he think he would need to generate in 2016? 2015? Then we focused on what actions to take the rest of 2014 that will start him down the path of success.

What do you suppose I plan to do at the end of this year? Yes, I want to find out if he achieved his goal. A lot of it will depend on if he made the same efforts after the coaching program that he made while we worked together.

Try the contrasting approach. Think of a goal that achieving would be really important to you. Then think about obstacles.