Why Entrepreneurs Should Fire Their Boss NOW!

Most entrepreneurs will tell you they love being their own boss. But if you worked for a boss who demanded a 50-80 hour week, asked you to postpone any time off indefinitely, forced you to pay for your own health insurance, micromanaged every detail, paid you well below market value, assigned you the work of five people, was hyper-critical, noticed every mistake and never complimented your successes, then asked that you defer your bonus until the company was “doing well” – you’d quit, wouldn’t you?

Sure you would. Yet most entrepreneurs are treating themselves like this every single day. It’s time for them to fire this boss, before it’s too late.

When I started my first agency in 1997, I had big dreams of working luxurious 5-7 hour days, starting my mornings soaking in creative brainstorming, with the sun streaming in my window, listening to my favorite music for inspiration, turning out gorgeous work that provided huge profits.

Within just a month or two, all that flew out the window. I was in my bedroom office working frantically by 6:00 am, and not stopping until I dropped by 10:00 or 11:00 pm at night. My health suffered. Deadlines were terrifying. My computer just didn’t seem to fly fast enough and my marriage fell apart, ending in divorce.

At the age of 29 I had no role model for healthy, effective leadership, having worked for bosses who themselves had no framework for reasonable work/life balance. What’s more, I really didn’t see myself as a boss. I saw myself as a very capable worker. In other words, I treated myself just like I had been treated in the job I felt compelled to leave. Oh! The irony!

The result was that for four very long, difficult years I hired under-qualified [also known as “affordable”] employees, just to assist me. Oddly, these individuals never quite seemed to be self-starters, and I was forever answering questions, even when I wasn’t there. In other words – I micro-managed everything.

Our agency’s work was good, but never quite great. The reactive quality stymied our growth and my own vision, so that each day was a flood of tactics that just never ended. We were doubling in revenue each year, as well as doubling our staff, but never quite matching that growth when it came to profitability.

It wasn’t until I hit a bottom of exhaustion and frustration that I finally began educating myself on what business leaders did to be excellent leaders instead of excellent workers. It took another two years to fully make the transition from working in the business to working on the business. I firmly believe that my long climb up is not necessary for everyone, and can be shortened tremendously. I also believe it is true that getting out of a leadership quicksand has a timeframe proportionate to the time spent stuck getting deeper and deeper in the quicksand.

So, here are the six things an entrepreneur must do right now in order for entrepreneurs to not only enjoy working for their boss, but also to model what healthy leadership looks like for future entrepreneurs :

HAVE A PLAN! It doesn’t need to be complicated, and it can absolutely change as the market changes, or as new insights provide new opportunities and direction. What it must be, however, is a map to: a. Who the business is b. Who perfect clients are, and what problems the business solves c. How the business will fund its initial efforts d. How the business will reach and woo new clients, from day one.


GET CLARITY! Every entrepreneur needs clarity about why they are in business. “Why” is a tidy word for “purpose”. It is a driving force far beyond profit or skill set. This “why” is the thing customers will ultimately buy – not the “what” of goods and services.

“WHY” becomes the crucible by which every decision is made: which customers to pursue and which ones to let go, who to hire, what product to promote, the right marketing message to deliver, and where to go next. Without a clear purpose, the entrepreneur will drift with inconsistent success, and ultimately be relegated to a commodity.

GET COURAGEOUS! The biggest challenge for most entrepreneurs I have met is fear. Fear has a thousand faces. There’s the fear of losing a big client, not having enough cash flow, not having enough time to meet the deadline, not staying ahead of the competition, or simply not being good enough. At its core, this fear is lack of self-worth.

The saying goes like this: “Courage is feeling the fear and doing it anyway.” I found this was my only way out of the seductive abyss of fear. Each time I walked over the fire, I realized just a little bit more clearly that what I was most afraid of hadn’t killed me yet. In fact, I was in a better place than before I had the fear!

What this looks like in practice is being afraid to tell a client, who is a poor fit (can’t pay for what they need, is disrespectful of your time, talent or expertise, needs something that is not in your core competency,) that the answer is, “No,” and saying “No,” despite the fear. Look at it this way – if the answer is yes, the business’ time is consumed by the wrong fit, and the right fit can’t get any time, skill or attention.

Or perhaps courage is standing firm in established pricing that is both fair and reasonable without needing to explain or bargain. Most clients actually want to consider the value offered, not diminish it – so stop trying to beat them to the punch!

SET PRIORITIES! Everything cannot be an equal priority, but entrepreneurs often try to leverage their super-human abilities and do it anyway: the hallmark of the over-committed. The result is chaotic and often results in missed deadlines, frequent crises, frustrated employees, up-charges from vendors, health issues, and lack of focus.

There is a spiritual component to setting priorities, since it requires reflection on what the entrepreneur truly values. Within priorities, certain things must come before others in order to move from point A to point B. A website needs content, so the content is a priority over the website.

Also, if the majority of the day is spent doing minutia – like answering and sending emails, then strategic activities go unfinished, making the minutia ultimately irrelevant. Obviously, setting strategy would be a priority, so dealing with emails must be limited. Opening emails just three times a day for 15-20 minutes at key times absolutely transformed my productivity!

KEEP AN OPEN MIND. An open mind is the key to creativity and innovation, which elevates an entrepreneurial business above the commodity mêlée. Markets shift, bubbles burst, technology transforms, and approaches are born. Ultimately, what any entrepreneur thinks will happen in the future is seldom the final result.

Therefore, when entrepreneurs attach to a particular outcome as 100% necessary, and try to force the solution they have decided is non-negotiable, the end result is exhaustion and frustration. Life doesn’t work like that.

Alternately, they can adopt an open-minded stance, where they are constantly learning, watching for new trends and alliances. This approach is energized. It is optimistic. It is worry-free. Open minds are creative, innovative and dynamically exploring everything around them. They also are as relaxed in the flow of life as they are curious about the flow.

To keep an open mind is to suspend judgment of right and wrong, good and bad, true and false. The open-minded entrepreneur is better able to navigate the changing landscape, and be a thought leader where others are caught up in how things are “supposed to be done.”

DELEGATE! Entrepreneurs are a self-sufficient lot – to a fault. One of the most common phrases from start-up founders is, “But I can’t afford to [hire someone to do it, outsource that, buy that automation tool].” For the entrepreneurs who are stuck in this story of lack and limitation, here are three simple questions to get unstuck:

  1. What is it costing you at your equivalent (hopefully respectable) salaried rate to do this yourself?

  2. What are you not doing as a result that would be in alignment with your salary?

  3. How long will you be able to afford to fund doing this yourself if you don’t hire/outsource/automate now?

The other issue with delegation is an unwillingness to allow someone/something else to help represent the business to customers. There is a fierce, self-limiting protectiveness of relationships, style, processes, and content among many entrepreneurs. If the entrepreneur has not built his/her organization from day 1 with the intent to delegate, they have built a self-limiting framework. Businesses grow and profit most effectively with a clear process. As a result, customers come to expect a team to support them, and get even better solutions than a one-person can provide.

Being your own boss can be incredibly fulfilling, and when done right, it demonstrates for future generations how work can be meaningfully successful for not only the boss, but for everyone involved. These six actions establish a culture that can thrive and expand without being dependent on any single individual. They also create the path for an entrepreneur to be the boss they have always wanted and have long deserved.

Like content like this? Join us in The Soulopreneur Project, a Facebook Group dedicated to helping solo entrepreneurs turn their passion into profit.

#GoodBosses #Passionatwork #businessdecisions #courage #worklifebalance #Entrepreneur #work #leadership #businessplan

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