Making The Transition From Accounting Employee To Entrepreneur

Have you ever thought about wanting to be in charge of your income, your clients, and your time? Do you ever daydream about a time when you don’t have to answer to anyone else but yourself?

If so, you’re not alone. Nowadays, more and more people are thinking about becoming self-employed, where they can make their own decisions about their careers.

Maybe it’s because of dealing with difficult bosses or because technology has made it easier to work independently, but many people, including accountants, are thinking about taking control of their professional lives.

Instead of working for someone else or with people chosen by someone else, we’re imagining what it would be like to be the ones making the decisions. Many accountants are considering breaking away from traditional ways of working and embracing a more independent approach.

Although there are ways to make traditional jobs work for you, being self-employed has its appeal too.

But there’s something important to understand: Most of us have been taught to be very good employees, not entrepreneurs.

The truth is that our education system was designed to train people to work in factories and follow instructions. It’s been teaching us to be obedient and to accept the authority of others for over 200 years.

The problem is, it hasn’t taught us much about being our own bosses. Transitioning from being an employee to being in charge can also be tough because our jobs become a big part of who we are.

Most people, especially those who have been employees for a long time, aren’t ready for this challenge. The idea of creating a new identity as our own boss can be scary and daunting.

The thing is, when you make the leap from being an employee to being your own boss, it’s like building a new version of yourself. But as I’ve shared on this podcast before, our brains prefer the familiar, so stepping into the unknown can be unsettling.

That’s why managing your brain is crucial when making this transition. Today, I want to talk about brain management and why it’s one of the most important keys to successfully becoming your own boss. Whether you’re already an entrepreneur or thinking about it, understanding how your brain works is essential.

The Importance of Brain Management

Whether you’ve heard me say this or not, this is the podcast where brain science meets accounting.  If you haven’t listened to any of the previous episodes, I suggest you go back and listen to episode #1 – “What It Means To Be a Smarter Accountant” and episode #2 – “The Place Where Brain Science Meets Accounting.”

In those episodes you’ll get a clear understanding of how your brain works and the two main systems that you need to get familiar with.  The truth is that your success as an employee or an entrepreneur will depend on how well you understand how your particular brain works and how to be the boss of it.  

Basically, your brain is like the control center, and when you’re thinking about making a big change in your career, your brain needs some special attention. Think of it like this: If your brain is a team, you want to be the coach. 

You need to guide your team through the game, making sure everyone is on the same page and working towards success. In the world of career transitions, managing your brain is the key that can make the difference between a smooth journey and a bumpy ride.

In fact, brain management is the key when you:

  • Feel scared to take a big step
  • Want to leave your job
  • Worry about what others might think
  • Can’t figure out how to organize your time
  • Feel overwhelmed by all the choices you have to make
  • Miss having coworkers to talk to about problems
  • Doubt yourself
  • Feel like you’re not good enough
  • Have a client who isn’t happy
  • Don’t have enough money
  • Are afraid to ask for more money
  • Feel like giving up.

The reason why brain management is so important when making the transition from accounting employee to entrepreneur is that your brain has its own way of doing things. It likes patterns, familiar routines, and avoiding anything that seems like a risk. 

But becoming your own boss involves stepping into uncharted territory – and that’s where the challenge comes in. It’s like convincing your brain to play a different game, and that’s not always easy.

The truth is that when you think about making a big change – leaving the job you’ve known for something new – your brain will throw up warning signs. It’s like a friend saying, “Are you sure about this?” 

That’s where brain management comes in.  As I mentioned, you have two main systems in your brain – one that reacts quickly and another that can look at the big picture.  Managing these two systems is key to a smooth transition.

Honestly, more than any other start-up tip or suggestion I can give you, managing your brain is the single most important thing that will determine your success, or not.  Again, you are actually going into business with your brain, so it’s super important that you understand how to manage and master it in order to make a smooth transition from employee to self-employed as well as continuing to be an entrepreneur.

Understanding Brain Management As An Entrepreneur

Like I said before, I’ve shared this in a previous episode of the podcast, but in order to understand brain management, you first have to get familiar with the two parts of your brain – System 1 (the Toddler) and System 2 (the Supervising Parent). 

While they work together, they have very different roles. Understanding how they operate is like having a playbook for your brain management strategy.

System 1 is your primitive brain and I refer to it as the Toddler because it wants what it wants, it gets scared easily, and it often throws temper tantrums like a toddler.  It is motivated by three things – seek pleasure, avoid pain, and conserve energy.

This part of your brain is like the autopilot that runs your life more than 80% of the time. It’s job is to keep you safe and alive and it takes its job very seriously.  

In essence, it loves things that feel good, hates things that feel like danger, and prefers everything to be in a familiar, comfortable routine.

Here’s the issue: When you decide to switch from being an employee to being your own boss, System 1, the Toddler is not onboard.  It wants you to stay in your familiar job, where everything feels safe and known. 

To this primitive part of your brain, the journey to becoming self-employed is not in its comfort zone. Think about it – the early stages are typically not immediately pleasurable, there will be discomfort, and everything will seem a bit confusing.

Thankfully you also have an advanced part of your brain that I refer to as System 2, the Supervising Parent.  This part of your brain is the prefrontal cortex. 

It’s the part of our brain that’s unique to humans and gives us the ability to think about what we think about. This is the part that can guide and manage the primitive brain of System 1.

In other words, the Supervising Parent can step in and manage the Toddler when it’s acting up.

For example, when System 1, the Toddler sees challenges like new experiences, possible failure, and confusion as big warning signs, almost like life-threatening situations, System 2, the Supervising Parent can step in and say, “Hold on, let’s think this through.” It has the power to override System 1’s alarms and help you face and conquer any challenge that comes your way during this transition.

The key is understanding that the Toddler part of your brain doesn’t want anything to change, but the Supervising Parent part sees the long-term, big picture and wants you to succeed.  Using System 2 to supervise and take charge of System 1 will make your transition from employee to self-employed much easier and much more manageable.

Making the Transition From Employee To Entrepreneur Smoother

So now that you know the roles of your lower, Toddler brain and your higher, Supervising Parent brain, I want to point out something very important – you do NOT want a toddler running your business.  In other words, you do not want your Toddler brain in charge when you transition from accounting employee to entrepreneur.

You’re going to want the Supervising Parent part of your brain in charge as much as possible if you’re going to have any chance at sustainable success.  You want to tap into your higher brain’s ability to see the long-term vision, to make better decisions, and to plan.  

When the Supervising Parent part of your brain is in charge more often than the Toddler, you will have the opportunity to make your transition from employee to self-employment much smoother.  

As I’ve coached many accountants making the transition from accounting employee to entrepreneurship, I want to share the three things I believe you need: 


The first thing you need is commitment.  To create the powerful feeling of commitment, you need to find your compelling reason for wanting to be self-employed. This compelling reason will serve as your North Star.

During challenging times, this compelling reason becomes your anchor, grounding you in your  purpose for becoming an entrepreneur. This is when the higher, Supervising Parent part of your brain can step in to reinforce your commitment, ensuring you stay on course.

You need to expect that the Toddler brain is going to freak out and try to convince you to not make a change, but have a compelling reason that helps the Supervising Parent do its job.

It’s having a gentle reminder and a reassurance that says, “I’m doing this no matter what.” In moments of doubt, The Supervising Parent can step in, solidifying your commitment and gently steering you back on the path to success.

Economic Responsibility

The second thing you need is economic responsibility.  The truth is that it can be challenging to not have a regular paycheck that comes no matter what.  That consistency and comfort is important to your Toddler brain which is why it does not like the idea of the economic unknown that often comes with entrepreneurship.  

In the Smarter Accountant 6-week program I teach accounting entrepreneurs in the making how to manage their brains because by entering entrepreneurship with a managed brain, you acknowledge that your efforts directly impact your financial security and you’re able to override the Toddler brain.

Again, your Toddler brain is in charge 80 -90% of the time and it is not onboard with making the transition from accounting employee to entrepreneur.  But by implementing brain management, economic responsibility is much easier.

By taking charge of your brain and utilizing the Supervising Parent to create value for your clients, you’ll see that every result you create, especially the amount of money you make, is within your power based on how you think, feel and act.

Emotional Maturity

And the last thing you need is emotional maturity.  I’m telling you, emotional maturity is crucial.  Understanding that feelings of fear, confusion, and doubt are normal, makes them easier to manage.

As I tell my coaching clients all the time, “Feelings are information, not problems,” you have to transition into entrepreneurship having emotional maturity.  When I refer to emotional maturity, what I’m saying is that rather than blaming your feelings on external factors, you instead understand how to manage your emotions on purpose. 

Emotional maturity is deciding how you want to feel and taking charge of your emotional responses.  This allows you to remain focused and committed on your entrepreneur journey.  

Emotional maturity means knowing that the only thing that can cause your feelings are your thoughts, and those thoughts are always optional when you choose them on purpose.  There is no place for the “blame game” when you become self-employed.

Hopefully, you can see that by focusing on these three areas, combined with brain management, you’ll be able to have an easier transition from employee to self-employed. It may be a bumpy ride, but there’s no reason you can’t make it as smooth as possible.

Becoming a Smarter Accountant: Making a Successful Transition From Accounting Employee to Entrepreneur

Now I want to share some stories of clients who became Smarter Accountants and made the successful transition from accounting employee to entrepreneur.

One client was a seasoned accountant, who wanted more autonomy and the chance to be her own boss. The problem for her was the shift from a secure job to entrepreneurship seemed incredibly overwhelming.

By recognizing the challenges she faced, I emphasized the importance of commitment. I helped her to get clear on her compelling reason for wanting to be self-employed.  

She realized that a strong desire for work-life balance and freedom were her most compelling reasons for wanting to become an entrepreneur.  I explained that we needed to get her brain on board.

With her Toddler brain initially resistant to change, she learned how much the Supervising Parent part of her brain would be the guiding force. By learning brain management it helped her to navigate through the challenges, ultimately establishing her own tax advisory firm.  

Today, she not only enjoys financial success but loves the newfound joy she feels in having the work-life balance and freedom she always wanted.    .

Another client was a CPA who wanted to break free from the traditional mold and create value on her terms. Her issue was she was used to getting a regular paycheck so the economic responsibility that came with self-employment was a big concern.

Once we started working together, she learned how to use the Supervising Parent part of her brain more often.  It played a crucial role in helping her feel much more empowered by the fact that her financial destiny was now in her hands.

As she became a Smarter Accountant, she took charge of creating value for her clients with much more confidence. She shared that the shift from being an employee receiving a paycheck to an entrepreneur in charge of her economic security was transformative. 

Today, she’s making more money than she ever made as an employee and she’s loving the power she now holds over her financial future.  

The last client was dealing with fear, doubt, and uncertainty as he was considering making the transition from employee to entrepreneur.  

By teaching him how to manage his emotions, we worked on building emotional maturity. Here’s where the Supervising Parent part of his brain took center stage, helping him recognize that he had control over his thoughts and feelings.

Once he became a Smarter Accountant by learning brain management, he faced rejection, fear, and self-doubt head-on. I provided the tools to manage these emotions purposefully.

Today, his firm is growing, he is building his own team, and inspiring them to become Smarter Accountants as well.  

Hopefully, you might resonate with some of my client’s stories.  As I say all the time, when you learn how to manage your brain, you can manage everything else, especially making the transition from accounting employee to entrepreneur.  

The bottom line is that you need brain management because you’ve been educated to be a good employee and your human brain is not wired to do anything outside of your comfort zone.  Thankfully, becoming a Smarter Accountant makes it possible to overcome any challenges you face but also make your dream a reality.  

There’s no denying that the journey from employee to entrepreneur is undoubtedly challenging, but with the right mindset and guidance, success stories like my clients can be examples of what’s possible for you as well.  

Well, that’s what I have for you.  Thank you for joining me as I discussed transitioning from accounting employee to entrepreneur.  I hope you’ve gained valuable insights and practical tools.

If you are struggling with any aspect of being an accountant, you can simply go to and book a free session with me.

I’ll explain The Smarter Accountant 6-week Program and how you can apply it to whatever you’re struggling with.

That’s what I have for you, but make sure you check back each week as I help you go from being a stressed accountant to a Smarter Accountant.

Make sure you go to and take The Smarter Accountant Quiz. You’re going to want to know if you’ve been underutilizing your accountant brain so that you have a starting point for becoming a Smarter Accountant.

Also, I would appreciate it if you could get the word out to other accountants about this podcast.  The more accountants find out about it, the more we can begin to change the narrative in the accounting profession.

The truth is that you’re already smart, but this podcast will show you how to be smarter.