How to Strategize Your Leap from Day Job to Dream Career   

“My job is soul sucking! At times I feel like I am dead.”  

Yes, those were pretty dramatic statements for me to make to my mentor at the time. I was going through the CTI’s professional coach certification program then, and as I grew my coaching business I was more and more in love with that work.  

By contrast, my work on an executive team for the United States Postal Service was something I was anxious to leave behind as quickly as I could.  

My mentor helped me to see that leaving my job too quickly would be stressful. It might be a temporary relief but the urgency to have income to support myself would not be worth it. I would be so dependent on getting new clients it would be harder to take the measured steps that make a business sustainable.  

I followed this guidance and built up my coaching business over time until I had the business foundation to have confidence I could succeed.  

Building a Business with Confidence and Patience 

Building my business to that point, though, took time to accomplish and there were many ups and downs!  

 In this blog post, I hope to give you some insight into your own journey to a successful career as a coach. AND to answer that much asked question: When do I quit my job?  

I will begin with a golden nugget of wisdom from a colleague of mine whom I interviewed for my book and on my podcast last year. Ann Farrell is as passionate as I am when it comes to our desire for coaches to succeed. We both believe this career is fulfilling and brings a much-needed dose of goodness to this world.  

When I asked Ann if she could offer just one piece of advice to coaches on this topic, her advice was very simple. Stop thinking of coaching as something you train to become. Think of coaching as a profession that requires training AND a career path.   

Here is an example. Let’s say you choose a career path for another profession such as being a doctor or a teacher. First, you decide this is the profession you want to pursue. Something sparks you to want to help people, and you want to do it in a specific way. Doctors and teachers help people in very different ways. 

There is a different kind of training and internship for each profession. The career path will look different. A doctor might want to work for a hospital or have a private practice. The doctor path might be niche-specific, such as a neurosurgeon, or it might be more general like a pediatrician. For a teacher, it might be working in a nursery school or becoming a college professor.  

Can you see how different those career paths would be? You can imagine all the different choices you would have to make about the training needed, the years it would take to put all the pieces in place, the income you could expect, and the lifestyle those different paths would create.  

Variety in Coaching: Choosing Your Path 

A professional coaching career also has its own variety of choices you can make. Here are a few.   

The entrepreneurial path is one where you have your own business. This usually includes choosing a niche and ways of marketing and making sales. There are so many varieties just with this one choice!  

The executive path could be where you want to work with executives as an external coach or contractor. Another choice would be to work as an internal coach — or you might want a bit of both.  

There is also the path where you choose to work for an already established organization that matches coaches up with clients. There are many different ways that you can work for a company that contracts coaches for one-on-one coaching.  

With these choices, you can add in many more options. Do you want to work only with individual clients? Do you want to work with teams or groups? Do you want to create your own coach programs and proprietary intellectual property? Or would you rather focus on training people using another coach’s approach?  

The Big Question: When Should You Quit Your Job? 

Now I want to look at that question again.  

When should you quit your job?  

This is also applicable to those of you who find yourself unexpectedly unemployed, whether because you’ve been laid off or for some other reason.  

You first need to make some choices on how you want to begin this professional career path. Put plainly: How do you want to make money????  

Funny enough, this part of the journey may require you to get some coaching! It can feel daunting to look at the options available for this profession when you are first starting out.  

The coaching community is one of the most generous I know of, so you can also reach out to other coaches for ideas and insights that will help you make this choice.  

Training and Career Building in Coaching 

With some clarity on this aspect, you now want to get the best training possible so that you will have confidence in being able to pursue this career successfully.  

I was fortunate to receive my training through the Co-Active Training Institute, where I now have the privilege of training coaches myself.  

CTI has been called the Harvard of coaching schools, and I have to agree.  

Now you have two important pieces in place: You have an idea of your career path, and you have begun your coaching skills training.  

The next pieces you will want to consider are what you need to have in place for your chosen path. If you are choosing your own business, you will want to create a business foundation just like you would for any other form of entrepreneurship.  

If you choose to be an executive coach, you will want to do some research and find organizations you would like to work for.  

This part of the journey is very individual in how long it takes to get to sustainable income. For most coaches, it takes at least 2 years to replace income from a full-time job.  

Does this mean you have to stick it out 2 more years in a job you hate? No, not at all. I certainly didn’t!    

The Path Towards a Coaching Career 

Similar to many coaches, I got hooked on the joy and aliveness that being a coach can bring.

So, though I took my mentor coach’s advice and didn’t quit my job right away, I did make a plan to make my exit ASAP.   

I did things to ensure my finances would be stable while I made the transition. Some of these things seemed bold to others. But to me, they were all worthwhile.  

I sold my house and bought an income-producing property that cut my monthly expenses in half.

I pulled some money out of savings to invest in my business. This meant I could not only afford to get trained as a coach, but I also got coaching and consulting support to build a business.  

My training included a business-building program that helped me build a solid foundation not only to get started but to be able to continue to grow and evolve. Gaining my Certified Professional Co-Active Coach (CPCC) credential gave me the coaching mastery I was seeking as well as the credibility with the public.    

The Co-Active Leadership Program taught me how to lead as the CEO of my own business and to lead workshops and other types of training. There was other training I got over the years once I was established and able to pay for them with my coaching business income!    

The other thing I did that really made the transition easier and quicker was to get a part-time job. I looked for part-time gigs that would align with my business.  

There were several of these over the years, and I liked them so much I decided to always have some kind of work with an established organization. I like having my own business and working for others.   

Sacrifice for Success 

There was also the sacrifice I asked of my family. I was married with a couple of teenagers at the time. To do my training and take time to build a business took both time and money.  

It meant my family would have to forgo fancy vacations and some other niceties they had become accustomed to. They would have to do more work around the house, and we had to look at their upcoming college expenses in a new light.  

I never felt guilty about this. I knew I was an example for my kids of following a dream and of doing what it takes to succeed in a fulfilling career. I was showing them that going for what you want in life requires discipline and adjusting your lifestyle. It can mean making money and having a lifelong career doing something you love. 

 If I could do it, so could they. So can you.  

The Reward: A Fulfilled Dream and a Flourishing Career 

With these things in place, I was able to quit my job about 18 months after I made the choice to make this my lifelong profession.   

It took me a few more years before I had built my income up to the point that I could support myself and a few years more before I surpassed my income from my full-time job.   

If you are making coaching your new career path, you have chosen a career that is as feasible and doable as any other career.  

Though it hasn’t always been easy — it has had its share of challenges as well as triumphs — coaching has been the most fulfilling career path I have ever had and has surpassed my expectations in every way.