How Creating a Strategic Plan Prepares you for Success

Want me to run SEO for you? 
Apply to work with me & my SEO team. I’ll research your SEO then reach out with next steps. 

We all have goals throughout our lives and yet time and time again we are derailed from seeing them through to the finish line. In this post, I will share with you a simple process for creating a strategic plan that will allow you to keep steady on your path towards the life that you envision.

My Experience as a Strategic Planner

I have been utilizing variations of this method for the past 10 years and I am elated to say that it has led me in the exact direction that I have dreamed of. Granted there are ups and downs, twists and turns that make you reconsider your true purpose, this method has served as a staple to the way in which I plan and approach my future.

If you’re interested in learning more about strategic planning after reading this post, download my free eBook titled Transforming your Dreams into Reality: A Theory to Self-Understand, Strategically Plan, and Believe. The book goes into further detail on how creating a strategic plan can lead to your visions becoming your current life.

Step 1: Understand Who You Want to Become

The first step to creating an effective strategic plan is understanding why you want to become who you are envisioning. It is important to understand the WHY first because it reaffirms the true reason you are creating the strategic plan in the first place. Let’s use an example to best demonstrate this first step.

Meet Mike. Mike is a 25 year old young professional living and working in the big apple: New York City. He has a good paying job, a simple commute to his office, a great group of friends from college and high school, and he shares an apartment with his girlfriend which helps him save on the crazy costs of rent. His life – as one may assume – is going quite well, but when asked the question whether he is happy with all aspects of his life, Mike tends to answer:

“well, yes, but no…I’m learning new things at work, but the culture is extremely stuffy…my boss is easily approaching 70 which makes it difficult for us to relate…and the work, well let’s just say that the work is not fully aligned with what I am passionate about.”

Mike has a different vision of who he wants to become.

From hearing Mike’s short background story and his response to one, quite open-ended question, we have an inkling as to why Mike has been sprucing up his resume and searching for different firms to apply to in the past two months.

When I asked Mike more about why he was beginning to seek alternative positions around the city, he answered:

“When I first graduated from college, I told myself that I wanted to find a place where I had the freedom and ability to creatively contribute to the growth of the company that I was working for. I also told myself that I wanted to find a position and a company where I was not restricted by bureaucratic hierarchies and required years of service before gaining more responsibility.”

Right off the bat, we have a couple of qualities that we know Mike is seeking in his next opportunity and that he is extremely passionate about. Hell, it was a vision that he had as a new graduate two years ago and he’s still been unable to achieve it.

Step 2: Envision your Ideal Life

The second step to creating a strategic plan builds off of understanding who you want to become. It is to envision your ideal life once your goal or set of goals have been achieved. The purpose in taking the time to do this and depict it in specific details is to fully understand where you are headed. With a clear end goal in sight, creating a strategic plan becomes simpler.

For this particular step, I encourage individuals to stick within 3 years so that you are able to be as specific as possible. Remember that you can always return to your strategic plan as you encounter unexpected events and experiences throughout your journey.

After speaking with Mike more about what most frustrates him at his current job, I left him with a piece of paper with a number of questions on it. I told him to give me a call once he had taken the proper time to reflect on and answer each question that I posed to him. Looking at me with a bit of a befuddled look, he reached his hand out and took the piece of paper. He said, “Alright. I’ll talk to you soon.”

Once I was well down the stairs and on my way to the nearest subway station, Mike returned to his kitchen table and opened the folded piece of paper. What he found was a slue of questions challenging him to think about his ideal future.

Iphone 6 Photos 739


I didn’t hear from Mike until three days later on a Saturday as I was finishing my run through Central Park. Mike sounded excited to be calling and he wanted to know when we could meet up again to discuss what he had come up with for his ideal situation. Breathing harder than normal and feeling the crispness of the fall air, I checked my calendar and proposed that we get coffee Sunday afternoon. Before being able to offer any other times, I heard “Perfect! See you then!”

When I arrived at the local coffee shop the following day, Mike was already there sitting at a corner table with two glasses of water and two coffee cups filled to the brim. After a few minutes of small talk, I asked Mike how it went with the questions that I had left him with.

Mike answered, “It was difficult at first because I hadn’t taken the time to think about those types of questions in quite some time. Probably since I was getting ready to graduate two years ago. But then as I got more into thinking about how my life could be instead of how it currently was, it started to get exciting.”

Mike and I spoke for over 30 minutes about the ins and outs of where he saw his career progressing to in the upcoming three years. As he spoke about his answer to each question that I had posed, I continued to ask him “Why?” to make sure that his answers and the envisioned steps forward truly aligned with who he wanted to become as an individual. From our conversation, it was clear that Mike was prepared to step out of his current situation and head in a new direction.

Step 3: Identify Key Milestones

With a clear end goal in mind, it is now time to officially begin creating a strategic plan. The third step to creating your strategic plan is to identify the key milestones that must come true along your path in order for your ultimate goal to become a reality. Milestones usually correspond to monthly or quarterly goals within your strategic plan, but can vary dependent upon the length of time you are providing yourself to achieve your ultimate reality. Milestones serve as a short term focus that you can strive for as you are working your way through the full strategic plan.


When Mike and I said goodbye after our afternoon coffee and discussion, I told him that I would be sending him along a new set of instructions to further develop his vision and that we should get back together in the middle of the following week. He assured me that he would reach out once he had finished the new assignment.

I arrived back at my apartment shortly before a thunderstorm started and I sat down at my computer. I pulled up a saved Word document that I had used in the past and edited it to agree with Mike’s current situation. I sent it to Mike, shut my computer, and headed into the kitchen for an afternoon snack.

This is what Mike received:

Iphone 6 Photos 740


When developing milestones for your strategic plan, it is important that you make them SMART: specific, measurable, achievable, results-focused, and time-driven. Without goals that follow these five criteria, there is a better chance that you will get lost somewhere along the way. Also remember that milestones give you a clear road map to achieving your goal, but they do not specify the actions that you must take to get there.

Step 4: Create Action Steps

The fourth step to creating a strategic plan is breaking your milestones down into actionable steps that you can incorporate into your daily activities. The actions steps that you create will provide you with a detailed answer to the question, “How will I make these milestones come true?” Action steps are tasks that you will perform on a daily and weekly basis to make your milestones achievable.

Mike and I got back together for lunch on Thursday after he had some time to craft his milestones and action steps. He began the conversation by reaching into his backpack and handing me the milestones and action steps that he had created based off of our conversation on Sunday. While I glanced over what he had created, I noticed the table begin to shake from Mike’s foot bouncing up and down. I looked up and said:

“Mike, I think that you’re ready to pursue your new vision. Let’s review your milestones and action steps to make sure that each is easily measurable and can be achieved with your desired time frame.”

He replied: “Thanks, I can’t wait to get started.”

When I got together with Mike in the beginning of this column, the focus on the conversation was his frustration with his current job and he felt as if he was trapped. Just a week later, our discussion became highlighted by the opportunity to achieve the vision that he had in his mind since he was a college student.

As we parted ways one final time, I gave Mike my final piece of advice to ensuring that his vision become a reality through the use of creating a strategic plan…

Step 5: Write a Final Draft and Post it Next to Your Bed

…”type up and print one final copy of your strategic plan based off of the feedback that we discussed today. Then, find a place in your apartment where you will see it everyday and hang it there. The more that you see it, the more that you will believe that it will come true.”

The more that you see and review your strategic plan, the more your mind becomes committed to seeing it through to the end. If you take the time to create a thorough strategic plan and then keep it locked up in a drawer for the next three months, your life can quickly take over.

Once you have a final copy of your strategic plan, it’s time to take action. Schedule action steps into your daily and weekly routine. As your strategic plan becomes a focus within your daily routine, you will witness as your ultimate goal becomes closer and closer each day through the realization of the milestones that you identified.

If you found yourself enjoying this column and the story of Mike from NYC, sign up to follow my blog and share a link to this column with your friends. You’ll receive weekly updates on new content pertaining to becoming an entrepreneur, growing your business, and strategically advancing your professional career.

If you thought that Mike’s initial situation seemed far too similar to your current life and you are interested in hands-on coaching to re-envision your future, reach out to me at Connor@ConnorGillivan.com. I am happy to set up a time to chat and provide as much useful advice as I can.



Want me to run SEO for you? 
Apply to work with me & my SEO team. I’ll research your SEO then reach out with next steps. 

Do you want to
better SEO?

Grab my 50+ SEO & marketing strategies to drive more traffic, leads, & sales to your business.

About Connor Gillivan

In the past 10 years, I’ve started 7 businesses & built two to $10M+ in annual revenue, teams of 30+ & an exit in 2019. Today, I run SEO & growth for my 4 B2B companies while teaching millions how to make SEO simple.

Do you want to
better SEO?

Grab my 50+ SEO & marketing strategies to drive more traffic, leads, & sales to your business.

Unlock the Power of SEO

Join 3,000+ SEOs, marketers, & entrepreneurs. Get actionable tips & strategies to start, scale, & monetize your SEO efforts.

Share this post with your friends

Article Comments

  1. Sheree Agueda

    March 1, 2016 5:03 am Reply

    I conceive this website has got some real superb info for everyone : D.

Leave a Comment

Want Better SEO?

Grab my 50+ SEO & marketing processes for free. Step-by-step breakdowns of how I run SEO for my companies.

Learn my strategies for SEO, content marketing, social media, CRO, partnerships, & more.