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Something strange is happening.

There seems to be a mass exodus of people abandoning their cushy jobs to reevaluate things and do work that’s more meaningful and flexible to their lifestyle desires.

After many months of endless Zoom meetings, working from wherever you can find a quiet space in your house, and losing track of how many days you’ve worn the same pair of sweatpants, people are challenging their own status quo.

Just this week I saw an article in Forbes highlighting that workers are quitting their jobs in record numbers despite companies offering raises and other perks to show their appreciation and try to retain their employees.

What is going on here?

I think people have had some time to examine their lives more closely and are wondering why they are giving their best energy to something they don’t really care about. 

I also think people are questioning their return to a daily commute, living in expensive and crowded cities, and doing work that feels like a complete mismatch to their soul.

I mean, let’s face it, we’ve all been through a lot. Many are feeling exhausted and traumatized and rethinking their approach to life and work. 

I personally know several people who are questioning the equation of work your ass off, pay your bills, and someday you’ll get to slow down and enjoy your life. 

Here’s my big question for you. What if the work you were born to do is waiting for you?

This is exactly what I was wrestling with nearly 8 years ago when I was laid off from my job as a software sales executive. Fortunately, I had started a side-hustle coaching others on how to find more alignment in their work. 

And as I sit here today, I can happily say that I’ve explored my potential in a way that has given me tremendous joy and replaced my income in the process.

I can also say that you shouldn’t quit your job unless you already have a financial cushion, a solid plan and some really good clarity about how you can leverage your existing skills and experience to make money doing something else.

Becoming a Virtual (Work-from-Home) Entrepreneur

Transitioning from full-time employee to a work-from-home entrepreneur can be a pretty big step for most people to take. This is especially true if you are used to a high income and really great benefits. 

After working as a sales executive in the software industry for 14 years, thoughts about leaving to do something else became harder and harder. It seemed like I had too much to lose by walking away. Then I was laid off in 2013 after a company reorganization. I was (mostly) happily employed one day and told I wasn’t going to have a job the next.

Fortunately, I had started coaching a few people on the side. This helped me create some extra money and build just enough confidence to consider going full time with coaching when I was laid off.

Around the time I was laid off, I was beginning to lose steam with my career and really leaning into the coaching work I was doing. I had been in the software industry for over 14 years and felt I’d done a good job and didn’t necessarily have ambitions to climb the ladder any further. 

One of the glaringly obvious issues with getting laid off was that I was only making $10,000 per year with my part-time coaching business and $150,000+ per year as a sales executive.

And that doesn’t include all of the benefits my employer provided like healthcare, dental, paid vacation, expense account, 401k match, and much more.  

So, I had a choice to make.

Do I look for another cushy corporate sales job or do I pursue the work that makes me come alive and come up with a plan to replace my high income doing something else?

After many discussions with my wife, I chose to do the work that was calling me.

I thought it would be helpful to break down how I did it and what I’ve learned after nearly 8 years as a full-time coach.

The Steps I Took to Transition My Work and Become a Full-Time Coach

It was Steve Jobs who said “You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.”

Here is my best version of connecting the dots nearly 8 years after leaving my career to become a coach.

1) I tested my business idea as a side hustle first.

It was important for me to know that I actually liked (nah, LOVED) my side hustle before jumping into it full-time. This was something I was going to be doing with the majority of my time going forward. 

With this in mind, I tested out my business as a side hustle for nearly a year before deciding if it was right for me. This was a year of ups and downs, failures and successes, and true moments of learning. 

I slowly but surely figured out how to take my idea from a hobby in year 1 to a business in year 2. Those 12 months gave me a taste of what working as a coach was really like. It was exciting, eye-opening and harder than I thought. But at the end of the day, I still wanted more.

2) I built a support network before I needed it.

During the year prior to being laid off, I was attending conferences for entrepreneurs and business builders. I would meet people at these conferences and ask if I could follow up and stay in touch with them.

Almost every Friday, I’d have a virtual or in-person coffee meeting with another entrepreneur or coach and ask them things like; “How did you get started?”, “How did you get your first customers?”, and “What are the biggest lessons you’ve learned along the way?” It’s amazing what people will share with you when you just ask! 

After a year of immersing myself in books, conferences, and networking with other successful coaches, consultants, and entrepreneurs, I had a built-in network of people who were eager to cheer me on and support me as I made the leap to full-time coach.

3) I prepared financially for the leap.

Outside of my wife’s yoga business income, we wanted to make sure this solopreneur venture wasn’t going to put us at too much risk. That’s why I spent the better part of two years saving part of my sales executive income to cover several months of our living expenses. This money in the bank gave me some peace of mind knowing that if it took me a while to grow my coaching business, we’d still be okay. 

I also had a severance package which provided an even longer runway if I needed it. And you know what? I needed it ALL. 

If you haven’t started a career transition fund, do it now.

Healthcare was another area we were concerned about. After researching several plans and options with a local health insurance agent, we realized we could get a plan similar to what I had through my employer. Because we were in relatively good health, we went with a high deductible plan to keep our monthly premiums lower. This ended up costing us close to $12,000 in 2019 when my wife experienced a major health issue but we had really good health insurance when we needed it most. 

Whatever you do, don’t skimp on health insurance.

Last but not least, we focused on lowering our expenses leading up to my career transition decision. We sold one car and got by just fine as a single car household. This reduced car insurance, maintenance, and repair costs. 

We also had a roommate to help pay the mortgage. We don’t have kids and we have a 4-bedroom house so this was an easier decision for us than most. Plus, the roommate was my wife’s brother. 😉

Important Lessons After 8 Years as a Coach and Entrepreneur

1) Owning a business is harder than being an employee.

Now that I’m almost 8 years into my coaching venture, I’ve realized a few things. The first is that when I was an employee, I didn’t realize the amount of benefits and perks I was provided. I definitely took them for granted.

The healthcare, dental and 401k plans were incredible. Now that I’m paying for these myself, I realize that I didn’t quite understand the monetary value as well as the emotional value of not having to worry about them.

Outside of those benefits, there was also the advantage of having the following departments at my company to rely on:

  • Accounts Receivable
  • Accounts Payable
  • Legal
  • Marketing
  • Research and Development
  • HR
  • Accounting
  • Customer Support

Honestly, this list could go on and on. These are all roles that I had to figure out myself as a coach. If a client doesn’t pay me on time, then I’m on the hook for hunting down that money. Or if I need to onboard a new virtual team member, that process is on me too. Same with marketing and selling my services.

Below is a detailed analysis I put together on how much I would need to make as a coach (in my case) to replace the income from my job. I figured out that I would need to make ~1.5X more as a coach to stay even because of all the benefits I gave up and the additional expenses required for running my own business.

As a sales executive, I made an average of $160,000 per year and I would need to be making somewhere close to $234,500 per year as a coach to break even. 

How much I needed to make as a coach to replace my day job income.

Having this level of clarity is important as you plan for your new venture. It will help you figure out how to get somewhere in the ballpark of what you were making at your job so that your lifestyle doesn’t take a huge hit. In fact, I’d guess this one step would either keep many wannabe entrepreneurs in their jobs longer or allow them to get more creative about how they are going to replace their job income.

One of the guys in my coach mastermind left his business and was making $25k-$30k per month within a year of becoming a coach. Part of this was due to his pristine clarity on how much income he needed/wanted to make to replace what he was used to.

2) You can’t do it all.

I knew that someone would need to do many of the roles I listed above (and more), and I quickly realized that it wasn’t going to be me. Unless I wanted to work 80 hours per week and risk burnout and hating my new “job”, I needed to get help. 

One of the first areas I outsourced was accounting and bookkeeping. Having a sales background, I figured I could handle the numbers. But, much to my surprise, business accounting was quite different from putting together my monthly sales projections. Once this task was fully outsourced, I felt much happier knowing it was being handled correctly by professionals. 

The outsourcing continued from there! I hired copywriters, digital designers, and virtual assistants to help with admin tasks. The work quickly became a lot easier, but this ate into my profits.

Now, I’m working on being more strategic with my outsourcing while creating more leverage in my coaching business. I want to be doing more of the work I’m good at while getting the rest off my plate.

3) Pivoting is crucial in times of change.

With the global pandemic still in play, I’ve had to continue rethinking my business model and how to make it work effectively.

What worked well a couple of months ago may not work at all this month. So as industries are changing, I am methodically pivoting my messaging and business model along with it. 

My in-person coaching engagements have transitioned to 100% virtual. I’ve postponed my peer group entrepreneur events since they rely heavily on in-person experiences and retreats. And I’ve started helping executives and professionals unleash their brilliance as high-impact coaches since so many people are re-evaluating their career right now and I can help them.

Is Entrepreneurship Worth It?

You might look at the above and think, “Woah, all that looks pretty risky!” And to that, you’d be right. I’ve worked very hard to learn and grow so that my coaching business continues to evolve and become more successful. 

But I also didn’t really expect to be where I was with my former career salary-wise for at least 3-5 years. To my surprise, I ended up getting there much faster – in about 2 years. All of the knowledge, skills, experience, and connections seemed to pay off. 

It hasn’t all been a smooth ride. There have been dips with income and wondering if I’d made a big mistake. My overall pace of net worth growth has slowed but the peace of mind from doing work I love is completely worth it.

In truth, income is not my #1 driving factor anymore. It’s more about the lifestyle that I’m creating. One that is focused on healthy living, time for adventure, and doing work that I love. 

I absolutely love every minute I get to work on my coaching business. I don’t plan to go back to being an employee any time soon.

Do I miss some of the benefits, perks and a regular paycheck? Absolutely!

Would I trade it for this new freedom and flexible lifestyle I’ve built? Not a chance!

With this rapidly changing world and economy, I hope this has provided you with some valuable insights and a glimpse into my journey from a full-time corporate employee to becoming a full-time coach. 

If you’re curious about the specifics of how I built my coaching business, you can read more about how I started and built a rewarding and profitable coaching business.

In the mean time, if you’d like to discuss how to unleash your brilliance as a high-impact coach so you can do more meaningful work, replace your job income, and enjoy more freedom and flexibility, let’s schedule a 30-minute conversation to explore what that could look like for you.

Until next time, live bravely.


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