The Entrepreneur’s Guide to Surviving a Mid-Life Crisis

When I was in high school, I was told I should become a lawyer. I guess it was because I was well-spoken with a knack for being persuasive. 

(Funny that no one was telling me to use my skills to be an entrepreneur.)

In anticipation of turning 16 and being able to drive, I reached out to Culver’s Alumni Director, Alan Loehr, and told him about my ambitions and asked for his help. He had me write a letter which I printed on resume paper (remember that?!) and he mined his database for 10 law firms in LA where we had Culver connections. 

I sent out the letter and got a hit with Marshack & Goe, a mid-size bankruptcy law firm in Irvine, CA. I interviewed with them, got an offer, and started that summer.

It was me and a kid attending USC law school - he was 22 and I was 16.

That summer, something incredible happened: the entire area of Orange County (where Marshack & Goe was located) filed for bankruptcy. The firm had a huge amount of business and I was putting my hands on work that was much more advanced than a typical copy/filing internship.

One day I headed to court with one of the partners who had taken me under his wing. He drove a Jaguar, talked on a mobile phone, and wore a Rolex. He looked every bit the part of the life I wanted to have.

Till he told me something I’ll never forget…

“Don’t become a lawyer, Andy”, he said. “I have all this money and no time to enjoy it.”

Turns out, the car was a gift to himself for the marriage that had fallen apart due to him working so much.

What is a Mid-Life Crisis? 

You know the cliches of a mid-life crisis: buying a new ride, getting divorced, and questioning life’s purpose are all classic signs. They involve feeling detached from work and feeling unhappy with what you're doing. Research from two economists has shown us that there’s a U-curve that people experience in life and there's this heightened early phase. 

But the reality is, people experience crises throughout their life. A mid-life crisis is only one phase. 

People experience crisis throughout life such as:

Quarter-Life Crisis: Anxiety Over the Direction and Quality of Life

This phase typically occurs during someone’s twenties through mid-thirties when they’re in the “young professionals” phase. They experience anxiety over the direction and quality of their life. They’ve been sold on ideas like being able to travel the world and live off passive income and be totally fulfilled. 

Later-Life Crisis: Contemplating Mortality and the Remaining Years

The later-life crisis tends to show up between 60 and 74 years old when the crisis has evolved into feeling lost and lonely, not enjoying family, experiencing a recent loss, and ultimately feeling sadness over the thought of dying. 

My point is that the crisis never stops. You will always be in a state of emergency if you don't do the internal work to let go of the judgments you have about your life. 

All your decisions led you to be exactly where you are. There's no such thing as an alternative life you could've, should've, would've had. Statements like these really don't exist:

• "I should have more money."
• "I should have been further along." 
• “I thought I’d be wealthier/married/have kids/etc by now.”

Judgments create stories. And when you compare your life to a story, you suffer. 

Entrepreneurs Pay A Greater Psychological Price Than Most

Moreover, entrepreneurs are prone to more frequent states of crisis because they pay a greater psychological price for their chosen profession. They're more likely to become emotionally attached to the ups and downs in business. They have more "Would've, should've, could've" mentalities around their life, and are revered as heroes (which is just another point in the drama triangle) but feel like imposters. This results in higher instances of depression, anxiety, and suicide than the general population. 

Related: How to Quit Trippin and Live a Drama Free Life

Signs an Entrepreneur is Having a Mid-Life Crisis and Its Impact on Business 

I don't see many entrepreneurs going through the cliché mid-life crisis. Fancy new cars, homes, and divorces aren't crises for them. They just buy shit when they're flush with cash, and the lifestyle either accelerates their relationships towards a life-long bond or separation.  

Entrepreneurs, in general, are always in crisis, and the signs typically manifest themselves in the business first before it hits home. Here are the business signs that an entrepreneur is in a state of crisis: 

Wanting Notoriety

You want to be known for all your accomplishments, but only a small few really know what you’ve done. 

You aren’t trying to use your achievements and experience to teach others. 

You’re wanting to use them simply to feed your ego. When the intent for status is ego-driven, you’re making yourself the hero of your business which is fundamentally flawed. 

Customers can see right through you and understand when the business is about you, or about them. Customers are the real hero of your business and you’re the guide. 

At my company Flow Marketing, this is in fact part of our secret sauce to personal brand entrepreneurs so that we help their business grow without making them look and sound self-centered.

Experimenting With Drugs 

Entrepreneurs are particularly susceptible to trying different pills and plants to go on psychedelic trips. While there are self-growth opportunities in these experiences, there are risks and consequences (which I talk about in my article, "Marijuana, Mushrooms, and Meditation").

Even though you may have had a significant transformation, the problem is when you rush to bring the same transformation into your business.

Your changes sound "off" to your team, and they dislike how you're disrupting their stability.

If you’re familiar with a DISC profile, remember that most of the population (and likely your team) are “high S” meaning they value stability. The majority of entrepreneurs are “low S” meaning they value change.

When you go on a "trip", be conscious of the change you’re introducing and the speed at which you’re doing so.

Becoming Bored With Business

You've designed a business you feel you no longer want to be apart of. You've accomplished a lot, but you need something to reignite the spark. In the meantime, you're going through rounds of hiring and firing in your internal team and supplier team because they're just not "doing it" for you anymore. I’ve watched founders start with mistreating their suppliers because it’s easier for most to fire a third-party than an internal hire. As valuable suppliers are short-paid, invoices are withheld, and their value diminished through dirty tactics, you see the founder is the one who is in a state of crisis. Once the founder’s ego feels confident to turn its dark stare internally, the firings and quittings begin.

Hiring a CEO / COO to Run the Business

You're ready to hire someone to replace yourself so that you move out of the day-to-day and into a more strategic role with a higher purpose. This role has many titles and for EOS companies, it’s called a "Visionary." The person you bring on may be a CEO or COO and they function as the “Integrator” to run the business based on the vision you provide. However, when you’re in a state of crisis, you lack the clarity required to give the company a vision. When that happens, the “Integrator” starts to bring their own vision to bear, and you find your company going in a direction you wouldn't have chosen, had you not been in crisis internally. 

When you're going through a crisis, so is your business. 

You risk everything you've worked hard to build: 

• Forcing your top talent to leave 
• Pushing your customers away 
• Lowering the quality of products and services 

All of which will cause your bottom line and happiness.

Selling the Business Because You’re Over With It

All of this will lead you to become desperate to sell. And when you're desperate, you sell for less. Which means, you've wasted a lot of time, money, and effort to create a business that didn't return the return on equity and the liquidity event you had hoped for. 

More importantly, the instability within your business drives further instability within yourself. And even if you do sell, it doesn't mean you've escaped the more significant issues at home and in your personal life. You have to deal with the root of the problem, your mindset, to really stop your crisis for good. I’ve experienced this myself and after selling my last company, I had resources but not fulfillment, and I went on my own spiritual journey. 

How To Deal With A Mid-Life Crisis

To deal with a mid-life crisis, you have to realize that you'll always be in crisis unless you do the internal work to get out. 

When you're in crisis mode, your body is in a sympathetic state, which is great for getting away from danger, but terrible for getting into a flow state. You need to get into a parasympathetic state (the Wim Hof Method can be extremely helpful here) to calm yourself down and then follow the five fingers path. 

The goal is to realize you're not actually in crisis, you're just allowing yourself to feel in crisis. 

Here's what you can do: 

1. Hire a Coach

There are tons of coaches out there who want to help you. Many are frauds, and many are amazing. Credible coaches aren't cheap, so I suggest making a real investment in someone with a real history of helping people. Find someone who will help you with the specific phase of your life, and don't be afraid to hire different ones. Just like athletes work with multiple coaches on different strengths and weaknesses, so can you. 

2. Join an Entrepreneur’s Group

Entrepreneur groups like EO or The OneFifty, not only help you with your business challenges, but these groups specifically help you identify your blind spots and share experiences around personal development that can help you evolve. And it's very comforting to be able to talk to people who really get it and that you can be completely open about the top and bottom 5% of your news — the things that you're not very comfortable sharing with anybody, or even your significant other. But when you can share everything about your business, your finances, your personal relationships, and what you're experiencing with people who get you, you can learn a lot and let go.

3. Become a Thought Leader

One of the greatest needs in the hierarchy of life is to achieve meaningful status and then fulfillment. When you start to look at your own life in a way that can be helpful to others, produce content and share it with others, you'll be able to achieve thought leadership around helping others with your experience. Which trust me, is far more fulfilling than searching for status simply to be famous.

There are two ways to become a thought leader:

1. Publish Content
2. Write a Book 

At Flow Marketing, we work with entrepreneurs to make them the most well-known authority in their niche. Many of whom have either already written a book or go on to writing a book once they see what their audience values from their content.

The benefit of publishing content is that you’ll create a marketing system that not only helps you teach others and raise your status, but you’ll also generate more business and new opportunities. One of the greater returns on investment is receiving emails, texts, and DM's from people you don’t know, thanking you and showing how your insights made an impact on them.

4. Meditate

I know that entrepreneurs struggle with meditation, I have as well. The big challenge is that there's so much on our minds, so many decisions to make, so much to think about, so much to worry about. There's so much, so much, so much. It's impossible to get entrepreneurs to go from a million to zero thoughts.

But I know you can go from a million thoughts to just ONE.  

The guided meditation I teach is for entrepreneurs: goal-oriented and focused on having one thought at a time. That way, you're developing concentration skills that will benefit you and your business. Plus, you'll massively destress your mind and body so you can make brilliant, more objective decisions through your crisis. 

5. Try Microdosing

Instead of jumping into a big "journey," with hallucinogens, try micro-dosing to enhance your meditation. You'll feel a more profound sense of connection and oneness without the risk of a complete and rapid ego-dissolution. Instead, you'll gradually dissolve your ego and the barriers that prevent you from feeling apart of something bigger than yourself. Also, I highly recommend starting a meditation practice first, then microdosing to make the experience even less risky. 

Related: Marijuana, Mushroom, and Meditation

6. Give Your Business Purpose

Stop bullshitting yourself that your purpose is to employ people so your business can provide a great life for your customers. If your business’ mission statement is to "provide high-quality customer service to make our client's lives more productive," then your purpose is bullshit. Period.

It's time to have an actual fucking purpose in your business. What I mean is, you need to make a social or environmental impact that's objectively measured, in addition to making a profit.

If you're not sure what kind of impact you want to make, then head over to B Corp and look at how they evaluate companies, then reverse engineer what you can do to get certified. If you're really unsure what to do, then create an apprenticeship in your business. How do you create an apprenticeship? That's a big damn answer that needs another article, so stay tuned. 

7. Embrace Innovation

Doing the same thing day in and day out will cause predictability and restlessness. The "I'm just going to do this the rest of my life," mentality will make you crazy-bored. 

The antidote you need is innovation. To get out of feeling trapped in a business that you no longer want to be apart of, you need to put yourself in a position where you can innovate the business itself. 

I don't just mean making the products or services better. I mean getting outside the box and testing something completely new. A word of caution here: don't let innovation consume more than 20% of your time and energy because you still need to protect your business's core. 

8. Sit on a Board 

Giving is the path to ultimate fulfillment. But as an entrepreneur, you need to strategically give without feeling burnt out. A great way is to sit on a board of a non-profit. 

Think about it for the moment. A non-profit startup needs your experience and expertise to scale. A board seat allows you to make a huge impact on a cause that's trying to help a community. Plus, you'll likely find yourself on a board surrounded with people who have similar values that wind up doing business with you. 

9. Affect Policy

Another way to become a strategic giver is to affect the policies that are not aligned with your value system. Educate yourself so you can advocate and get behind politicians and organizations that want to make the change you want.

You can serve in a volunteer leadership role to help a politician during election season. Or you can financially back a candidate to boost the chances of success. You can also get involved in your cities chamber of commerce or government committees to make an impact on specific local issues you care about.

No matter what path you choose, there will be immense personal gratification when your hard work or money helps a leader or organization make significant changes for the world you believe in.

Last Thoughts on Surviving a Mid-Life Crisis

If you ever find yourself saying, "I'm just feeling so lonely" or "It's lonely on top," then you’re suffering when you don't need to. 

Surviving a mid-life crisis as an entrepreneur means you're going to face additional challenges outside of what the typical mid-life crisis looks like. Thus, it's even more important that you are consciously aware that you have options and resources.

There are plenty of entrepreneurs who have gone through very similar things as you. Plenty who have navigated them well and plenty who didn't. You can learn from all of them. Entrepreneurship is a journey that's not meant to be alone. Find the help you need and do the work that needs to be done. 

Any crisis — quarter-life, mid-life, later-life — is a state of mind. 

If you don't do the work, then this crisis will only evolve into the next. You'll always be stuck suffering when everybody deserves a life rich with happiness and fulfillment. 

If you're curious about what the inner work looks like, then start a meditation practice. Check out my guided meditation and read my book Bling.