July 26, 2023

Your replies to “Why did you start your business?”

Thanks so much to everyone who replied to my last message asking about your motivation for starting a business!

I normally request explicit permission to share replies but in this particular case I made an exception because there were too many for that to be practical.


I read through every one and made sure to edit just enough to keep them anonymous without ruining the sentiment.

(NOTE: If your see your answer below and feel overexposed, just let me know and I’ll remove it from the web version of this post.)

With all that said...

Here’s what folks here on the daily list had to say about why they started their business (lightly edited for clarity and anonymity):

So I could have control of my schedule. Hated the thought of only weekends and two weeks at my disposal a year... and investing my sweat equity into someone else’s dream.

Flexibility to raise my kids at home and still make $$!

To spend less time working and more time with the important people in my life while remaining financially stable.

Flexibility to be there for my kids

Freedom to take vacations when I choose

Autonomy to decide which projects I work on


Bottom line for me: I have a unique perspective on how to serve my niche based on two decades of experience, and I’m 100% confident it works. I can’t in good conscience suppress that and work for someone else, falling back to the old-school, mainstream approach. I feel morally obligated not to deprive the world of my contribution. It’s also a lot of fun!

To reclaim agency over my work, time, and life.

To quit chasing meaningless titles.

To not have a manager anymore, but rather clients who were true partners in the actual work.

Because after a layoff and a severance float, I saw very little risk - you can’t become more unemployed, why not try stringing contracts together 😊

I started a business because the pain of not starting one became too great.

A business is what I need to start if I am to make it alive in this time in the world.

I started a business to share knowledge, be of service, make beautiful things, and GET PAID!

Independence. Legacy. Create & capture value.

I have health problems and wanted work that focused more on results than hours. Though I technically could have gotten that as an employee if I found the right job at the right company. I don’t know of any company doing what I’m try to do though, so there is that.

Why I started my business: I believe that success happens when we find a better way & are able to share it.

Simple: freedom.

To have the freedom of doing what I want when I want and with whomever I want.

Two reasons why: i) to have autonomy over my time and attention; and ii) to build life-changing wealth.

So I could only work when my kids were at school :)

After unexpectedly being let go by my former longtime employer, I vowed never again to let a boss have that kind of power over me. And that’s the real reason I started my business.

Moving effort from obedience to other people’s goals to seeking and fulfilling goals meaningful to me.

Because I realised I was trying to steer someone else’s ship.

I haven’t found an employer that would pay me enough so my family can rely on solely my income alone.





I get hives being told what to do, and when I’m under “obligation” to show up for someone else.

Plus I like the adventure

Of it being my own project

My own experience

That no one can take from me

And there’s nowhere for me to hide

It’s just me

Plus I generally think I’m smarter than the average bear.

And I have no patience working for or with average bears.

To have more (perceived) control over my own business destiny

Initially it was just a project to help me learn faster and make connections in a new industry that I was excited about. It grew into a business as the opportunity became obvious.

We started our business to be more independent. Being employed limits us and makes us more dependent on other people’s decisions about how to help which people as well as the level of niceness of our living. One could argue that there are lots of companies and opportunities for an employee, but in reality employee gives more power to other people, is more at the mercy of chance in that kinds of important decisions.

I’d prefer to make my own mistakes, than be told to implement the mistakes of other people!

It melts my soul to take orders and to do things that aren’t my way.


Doing it for myself... rather than doing it for someone else. I am a terrible employee!

I wanted to have fun doing what I do

I’ve asked myself this a lot of times and some time ago I came across one psychologist video on youtube where she pointed out, that some people want to start their own business because they had "controlling" parents and these kinds of people can’t stand than somebody (like a boss) is controlling their life at work, so they go for being their own "controllers".

I started my own business because I couldn’t stand being managed the wrong way.

I can’t stand the thought of having a boss but i would lie if money wasn’t a strong motivator. As employee there is always a limit.

Control over my time and higher earning potential.

For me it’s an egocentric motivation:

1) the freedom to work anytime from anywhere I want, with clients I love working with.

2) a lifestyle where money is never an issue when considering opportunities

So I push all the buttons.

More than one reason, but most of them related to freedom!

I want to be able to get hyped and interested in different things at different times. Having my own business makes that much easier and I get to explore so many topics.

Depression is another one. I used to have a lot of up and down periods, when I’m super productive or when I just want / need to stay in bed. I felt bad for my employer. Now I can exploit that and make it work for me.

To employ other working mums, give them the training they need, and pay them well in a job that fits their lifestyle: fully remote, work whenever you want, no time quota just get the job done, kids welcome on calls, we all understand when kids are home sick and they work less that day etc...

Therefore, my business goal is to hire as many people as possible! We’re 9 so far, I plan on reaching 15 by the end of this year and 40 in 2024.

Initially, it was to get the flexibility to work only 4 days a week so I could spend time with my son instead of putting him in childcare (which in the UK would probably have cost about the same that I would have earnt in that day). And that flexibility remains one of the main reasons today.

Reasons: directly participating on my work input/creativity, do more, get more freedom to decide who to Work with and being flexibel with my time schedule.

Flexibility and able to solve problems my way which is itself a problem 😂😂. Being a Ui/Ux designer, I figured I am often my client’s b word.

I am in the process of trying to step out on my own. There are two reasons that immediately come to mind:

1) Rewards. I put as much effort and stress into my employer’s business as if I owned the company myself. They get 110% from me. At some point it dawned on me that I was NOT getting the same rewards that I would get if I put that energy into my own business. Since it’s not in my DNA to just “phone it in” at work, I decided to channel my efforts into something that hopefully reaps those rewards.

2) Control. I am pretty sure I’m always right but smart enough to know that can’t be true. But still, I grew tired of watching the company’s I worked for do absolutely stupid things. Climbing the ladder appears to be some sort of rigged system that barely has anything to do with meritocracy. I decided that I can either figure out how to play that game to get into a positions of authority (and reward) or I can skip all the BS and go to the head of the line with my own company. I’ve decided on the latter instead of the ladder.

My neurodiversity (ADHD & Autism) make it really hard to follow rules and work with irrational decision makers. My experience in the workplace (2 years when I was 18yo) left me so drained that I decided to dive into my innate entrepreneurial sense and never look back. I must say, I’m the only one in my whole circle making 100K+ a year. It’s sad that not everyone has the urge (or even ability) to be their own boss, a decentralized workforce would be much better for the economy and mental health.


Don’t like taking orders👿 (Seriously, though - if that’s the case, I should get myself some new clients!)

Stop making money for somebody else and just do it for myself – that was the original reason – but the reason I keep being self-employed is the freedom to set my own agenda/schedule.

To be free (= wake up and do whatever the f*** I want)

To not have to work in an office

To not have to small talk all day

To be and be seen as independent

To be able to choose my own projects

To make a s****load of money

To be succesful and admired

To feel useful by helping others

To be able to have time for things like painting etc.

The reason I started my business is because I wasn’t making a nice living working for someone else. I came to believe that I had to go out on my own to make a nice living.

I learned the hard way that working for myself didn’t automatically fix that, either. 😖 But I’ve learned a lot over the last ten years. That’s another story. 😊

Freedom and therefore happiness/purpose. Live where, when, and on what I want. Build and compound passive income.

The REAL reason I started a business is because after turning 35 I developed FOMO after seeing my previous employer rake in $millions.

First... love your daily messages, Jonathan! Huge value!

1) done being stretched thin as a highly desired expert in-house without a backup or ability to say no to the next incoming gig that needed strategic or biz dev support. This was a signal my skills were unique and in demand.

2) opportunity to capture the margin! My clients have no problem paying what is perceived to be about the same for my consulting, whether I’m invoicing directly as an individual or just a line item in a monthly invoice from the agency I was previously employed by.

3) realized I could have more direct impact and build more trust with my clients when not embedded within the software teams they contracted for hire (or it’s my hypothesis to combat the Us vs Them when stuff gets messy)

Seriously, I could go on and on and have no idea why it took me over 5 years of misery to figure this out.

I started my own business to have control over my time. A secondary reason is to have a vendor-client relationship, which is more equal and collaborative than the superior-subordinate arrangement that is typical of an employee.

The REAL reason was mobility issues and pain. Being able to work from home removed several stressors from my day that as they say, “used up many spoons”. I looked at my skill set and knew what I had to offer was needed by many smaller companies that did not have a need to have a designer full time in house. At that time it was mostly print but morphed into web. I’ll be hitting 20 years in the fall. I can’t help but think I wish I had the energy I had poured into the companies I had worked for that I poured everything into with the “gold watch be here until I retire” mentality.

I’m really looking forward to hearing the results from this survey! Especially how people stomach the risk.

I wanted the freedom to accept or reject projects that came to me. Whereas at staff positions, I usually had no choice but to work on whatever project was assigned to me.

Because when I started out I had some skills but no experience, so I went freelance instead of getting a "job".

For me, it’s freedom.

Not financial freedom - I know I’d make a heck a ton more at another job.

Not even really time freedom - When duty calls, it calls, although I do seem to have a lot more time with the fam working the business.

For me, it’s the freedom to live up to my standard of integrity.

The few jobs I had were simply awful in one way or another. Sly tricks, misrepresentations of truth, etc. And it made me sick to my stomach every time and led me to turn in my 2 weeks notice the next day haha.

Anyways, so that’s my real reason.

Thinking about it, there are probably three criteria that make my side business different from my day job:

1) Bandwidth throttling: I decide how much or how little to work. I can go through intense periods (creating a new book, offering a lot of coaching, etc) and then downshift to quieter periods (close my coaching program for a few months, only write the daily post).

2) No upper bounds: At work, my total comp package is the most I’ll make. If I want to make more, I have to ask for it or get a new job. In my business, there is no upper bound on my revenue & I don’t need permission to make more. (That doesn’t mean it’s always easy to make the next jump in income!)

3) Editorial choice: I choose the topics I write about and the projects I work on. At work, I don’t always get to pick my projects. Some of them are dull or I disagree with the strategy. With my business, I try to make sure I’m enjoying it & I’m the one setting the strategy. (That doesn’t mean my business is always fun, though. Ha!)

Initially for being more independent and deciding my schedule.

Then I realized that there were way more pros:

You decide the clients you work with. It’s harder in general to get forced to work with bad clients.

In general, a higher income.

No schedule also means no balance. Some weeks you work a lot, other weeks you don’t work so much. I value this, and prefer this instead of a regular routine. Right now it’s not possible, but my dream would be to work like crazy for 3 months, and do nothing or personal projects only for the rest of the year.

Optionality: an employee often isn’t exposed to business options, only their employer is. A freelancer in general can benefit more from options and opportunities. It also depends on luck when the freelancer is not known much, but it happens from time to time that crazy requests come in, which bring in 5 figures in a month or close to it. An employee’s salary is stable, but for them it’s more difficult to get those unexpected requests that boost their income.

Being a peer with clients. If the freelancer knows at least the basics of client management, they can be their business partner. Your advice is more valued by clients, they listen, and there’s a less stressful relationship in general.

Employees often have all their eggs in 1 basket. Losing a job for 99% of employees means seeing their income switch to zero overnight. If this happens after a certain age, it can be even harder to find a new occupation. A freelancer spreads his risks over different clients. Losing a client isn’t a big deal, because there are other active clients.

A more diverse and valuable network. Probably related to optionality. Business opportunities can generate more business opportunities. Several of my past clients manage affiliate marketing websites. If one day I want to launch a product in their space I can contact them. Maybe I pay them some consultations, maybe I just send my product to them for free so they can test it if they’re interested.

Always decide for the best approach on projects. More control in general over execution. There are no coworkers to deal with, that could force you to use this or that framework, for example. You do your own SOPs, no one forces you to follow the SOPs of someone else.

Working as a self-employed or as a business is harder. You’re often alone. I still value this extra effort because it keeps me engaged, and it forces me to improve. Slacking off as self-employed can be expensive, it’s harder to do it. This motivates you to stay updated, and competitive. I’ve known devs with 20 years of experience that would be worth close to nothing outside of the company they work in.

I can probably go on forever :D

I know a lot of people who are working for minimum salary and banks don’t want to approve them loans. For some people starting business is only option for better life and fulfilling their wishes.

Of course the most important are being CEO of company, much higher income and meeting with important people in companies.

This is my opinion and have a great day.

I was looking to escape office politics and commuting. I did IT Director / IT Guy type work for nearly 20 years, and the longer I did it, the more aware of what a waste of energy both were. I also wanted to work on something more meaningful. My lifelong friend and I always wanted to start a business, and opportunity knocked, so we went for it. Our story is still being written, so I am betting on the long term, but as of 11 years in, I could make more money working for someone else. However, I gladly accept a little less money over the other tradeoffs made working for someone else full-time.

I read “The Four hour workweek” for the second time in 2014. It inspired me to get started in online business.

Financially, I have long had a goal of achieving a top 1% income (I.e. over $300,000 in Canada). Achieving that income as an employee is highly unlikely. Therefore, business is the best route.

I also want the whole freedom to take days off, work from home etc as much as I want.

Freedom and autonomy is the main reason for me. I take responsibility of my own destiny directly based on my actions.

My business is just me as a freelancer, so my motivations were quite simple and personal.

I have a feeling your question was more about grand purpose or vision?

So I could be location independent, and generally time flexible.

So I wouldn’t have to go to the bathroom in crowded public toilets.

So I wouldn’t be crammed in small offices and cubicles beside people munching on snacks, vaping, or clipping their toenails at their desk! 😩

Because after about 3 to 6 months, I get sick of doing the same thing, or being in the same place.

My friend talked me into the tax benefits of a Canada corporation when freelancing/consulting.

Otherwise, the help I give my clients is very similar to what I did in-house. And I’m so much happier without the constant bombardment of physical indignities of office life.

Fully remote work changes this equation. And I do sometimes think about getting a steady role with a company.

But I also have an overactive sense of ideas and possibilities. I think about going back to school, and switching fields. And I’d like to develop more of my own products, tools, utilities, and art. And I think I’ll have more flexibility to do that on my own. Could be a total fantasy/fallacy!

I hated corporate life (all hands meeting! new mission statement!) and wanted to control my own schedule.

For me, it’s about the freedom to choose how I plan my day.

I started my business for flexibility and freedom. I will NEVER put in another PTO request!

I started (or trying to start) my consulting business because I think I might be in more control of my growth than being in a job. If I can manage myself and control my time (which is hard) I can decide where and whom to spend my time with, and If I´m lucky enough (work my ass off consistently and learn from experts) I can earn more money than in a budgeted job.

I guess this is like a sort of "freedom" , which for me means: be where I want + fight for my own income. (I don’t picture myself working 1 hour and surfing ther rest of the day in Bali like the gurus try to sell)

I didn’t want to work in an office. I didn’t want to commute. I didn’t want to work for someone else and make them rich while we were paid peanuts.

Didn’t want to finish college

Here’s the thing...

Notice any big patterns?

I do.


  1. Freedom
  2. Flexibility
  3. Control

Several replies mentioned money-related issues - and that’s obviously important - but I wouldn’t put it in the top three.

So the question becomes:

If freedom, flexibility, and control are your top reasons for starting a business, how well is it working out for you?

In other words...

Are you running your business, or is it running you?