7 Things I Gave up to Pursue My Entrepreneurial Endeavors

Casey Botticello


Photo Source: Andreas Klassen of Unsplash

I’ve read a lot of articles espousing the benefits of being an entrepreneur. And there certainly are positive aspects, such as the freedom to pursue your vision for an idea or company and the potential for long term accumulation of wealth.

However, there are a number downsides to being an entrepreneur. More specifically, there are a number of things you give up.

Below are 7 of the things I had to give up in order to pursue my entrepreneurial ventures.

1. Security

When you are working a traditional job, it is easy to forget that you generally have some sense of security. As soon as you commit to pursuing entrepreneurial projects instead of maintaining traditional employment this becomes abundantly clear in many ways:

  • Margin for Error — Most companies have some built in margin of error that they allow employees before firing them. At a minimum, it is likely cost prohibitive at most companies to arbitrarily fire employees. As an entrepreneur you are constantly faced with small decisions, any of which can derail your project or business.
  • Healthcare — One of the most effective forms of “Golden Handcuffs” that American employer have is healthcare. It may not be a great plan, but navigating the healthcare market as an entrepreneur can be distressing and time consuming. If you have a chronic condition, as 60 percent of Americans do, this is a major concern. If you have family relying upon your traditional job for benefits, the potential risk is extraordinarily high.
  • Retirement — Entrepreneurs need to consider what’s going to happen after they retire. A common problem with entrepreneurs is that they are so focused on the present and creating a business, that they neglect planning for retirement. Planning for retirement is harder for entrepreneurs because of the irregularity of their incomes and less options than many working traditional salaried jobs.

2. Relationships

Entrepreneurs do not need to sacrifice all relationships for the sake of their own personal success, but having a job with irregular hours, high personal accountability, and sporadic bursts of stress makes it difficult to keep up with friends and family.

It is even worse when it comes to dating. In my experience, anything that deviates from the societal norm (working a traditional job) may be initially seen as exciting by a potential partner but it is quickly viewed as a personality flaw. It is very hard for someone working a traditional job to understand the pressure and effort required to keep an entrepreneurial venture alive.

3. Complacency

Complacency is generally viewed as a negative trait but it is also a luxury that most entrepreneurs will not experience.

Creating a new business or entrepreneurial venture is hard. Keeping it afloat while competing with larger businesses or well funded individuals is even harder.

This typically involves constant attention to detail, strategizing, adapting, and having a clear understanding of market realities.

None of this lends itself to complacency, which allows you to coast by by putting in “average” or “acceptable” levels of effort.

4. Routines

While many writers/growth hackers swear by the benefits of routines (i.e. get up at 5 a.m. every day or do these 5 things before lunch), my experience has been that being an entrepreneur requires you to let go of routines.

That is not to say you won’t form new routines. You almost certainly will.

But most routines are difficult to maintain.

I would say that flexibility and adaptability are far more important to most entrepreneurs.

Your schedule is constantly in flux, you have unexpected opportunities come up which demand a disproportionate amount of time and focus, and you are typically filling multiple roles for your business.

5. Vacations

Entrepreneurs are obviously allowed to take vacations.

After all — isn’t that sort of flexibility one of the benefits?

Yes and no.

If you are the sole entrepreneur working on a project, it is hard willingly allow your businesses growth to suffer. Even if you are overworked and desperately need a vacation.

Even if you do manage to take a vacation, it will almost certainly be a working vacation.

I actually prefer to work everyday, regardless of what day of the week it is or where I am, 365 days per year if that means I get to pursue projects I am passionate about.

But this lifestyle is certainly not for everyone, and it may lead to problems as the majority of the world is not operating under the same assumption.

6. Stability

Financial stability is amazing and is definitely something I can appreciate.

But a major shift for me, as someone who loves personal finance, is learning to live without financial stability.

The level of financial risk varies depending on your financial resources, living situation, and the cost of your idea.

That is why many entrepreneurs start off with a “side hustle” which is a good way to test an idea without quitting your primary job.

But regardless of how prepared you feel, there is always an element of uncertainty.

7. Trophies

There are almost no external rewards for being an entrepreneur until you have had major financial success. And this can literally take decades.

A traditional job offers you a steady stream of titles and clear promotions, which is much easier to internalize as being successful.

This can be disheartening sometimes, but it makes those rare moments of success all the more worthwhile.

I also think this form of delayed gratification is a true gift in a world where most people are looking for a quick dopamine fix, whether it’s through a like on social media, or a literal award for a job well done.


Despite the things I have sacrificed to pursue my entrepreneurial ventures, I am overwhelmingly happy with my decision.

I wrote this article to help balance the prevailing narrative which seems to suggest that entrepreneurship is all about freedom. In some aspects, it certainly is.

But, like any other decision, choosing to start a business, create a product, or perform any service outside the traditional economy comes with trade-offs.

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I am a digital marketing consultant, entrepreneur, and private equity investor.


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