Ten surprising benefits of self-employment | Year 1 Reflection

The benefits and upsides of self-employment are priceless and often overlooked


When I took the leap to self-employment, it was an act of desperation. I had lost faith in the leaders I saw around me in the business world, felt disconnected from the work I was doing and had started to question whether I would be able to stay true to my leadership principles that I felt were slipping.

What I found in my journey of self-employment has been a shocking amount of upside and unexpected benefits. If you follow the #futureofwork conversation in the media, you read mostly about people being exploited and underpaid, people without benefits and financial insecurity.

These are major issues that need to be solved but if you dig deeper into the research you find that despite all of the downsides, people are choosing self-employment over traditional alternatives.

When people ask me about working on my own, they say things like “I could never do that, I need to get paid every month.” While financial insecurity is real, most miss are the enormous upsides, many of which I could not have anticipated until I had the courage to take my leap.

#1 Doing things that matter with an “opportunity mindset”

To be a successful full-time employee, you must navigate a complicated system of “hoop-jumping” as William Deresiewicz noted in his famous commencement speech. You focus all your energy presenting yourself as someone that meets a standard.

I was an accomplished, if not excellent, hoop jumper. I even created a 45+ page “Career Transition Playbook” that I give away for free since it never really felt right to monetize my knowledge of a system so focused on the wrong things. The problem with this system was that it is impossible to get through the hoop-jumping without telling some sort of marginal lie about who you are and what you hope to achieve.

Being self-employed, an “opportunity mindset” flips this broken paradigm:

1. Put myself out there in the world as I am

2. Look for opportunities that look interesting or people that inspire me

3. Connect with those people or groups and share my story fully

4. If there is a connection, find ways to work together and see what happens

Earlier this year, I was at a memorial service for the founder and director of the grad school program I attended. During the service, several people spoke of this man’s commitment to the community.  I admired this and I felt pulled to find a way to offer myself to the program.

I e-mailed one of the professors asking if I could help and he proposed that I be a teaching assistant for the summer leadership seminar. Taking this position made no sense from a financial perspective, but made complete sense in my new self-employed universe.  It was the point of becoming self-employed: having space to say “yes” to things that mattered to me.

#2 Being forced to define my own success

by Volkan Olmez on Unsplash

In the corporate world, I always received the most praise when I started a new job or got a promotion. Combine this with the ability of anyone to take your title from LinkedIn and plug it into Glassdoor to see how much money you make and your definition of success (even if you have one) is undermined by our collective obsession with money and status (and our ability to figure out where you stand).

A feature and a bug of self-employment is that you have no idea what people are making and you have no way to judge them. This forces some to ask you about what you are working on. While people do still ask about extrinsic factors (“how big do you want to get?” “how many people do you want to hire”), it is more natural to shift the conversation to the definition of success I have defined.

While many people still think my goals may have to do with money, self-employment forces a shift to think about how to live a life you are proud of rather than thinking about your job or career above all else. In his book Skin In the Game, Nassim Taleb echoes this sentiment which closely aligns with how I now think about success:

I will keep mentioning that I have no other definition of success than leading an honorable life.”

#3 Not Being In A Rush

In the corporate world, there is always a sense that you could be moving faster. The two years I spent in New York were the most extreme version of this. Someone once said to me, “you’re doing well for your age” which must have meant I was headed in the right direction. Personally, I was already plotting my escape.

A career is an artificial path which you must always manage, have a story for and be networking so that you can take the next step. The next step being up, of course.

Being self-employed, there are no promotions or paths to judge yourself against. Other people’s confusion with this fact comes out when people invariably ask “what’s your plan?” or “how’s business doing?”

While this question has no answer, I respond with what I know to be true: “I am following my creative energy and seeing where it takes me.” This tends to drive a lot of people who are deep into career thinking a bit mad.

The poet David Whyte offers the idea of the “pathless path” which I take to mean that there may be a general feeling that you are headed in the right direction, but that you may not know which direction that is.

Staying true to my inner creative drive and trusting that things will work out forced me to put faith in other people, see myself as part of a bigger community and world and think deeply about how I can be a more generous member of this world and my communities.

#4 An escape from the inevitable insanity of corporate cultures

by whoislimos on Unsplash

While the corporate world embraces teams, careers are an individual sport. While I may have been praised for helping others in my jobs, I would not be promoted, given a raise or good bonus without shameless self-promotion.

Managing your reputation and any gaps between perception and reality are perhaps the core work of a full-time job and career. Lacking strong cultures to transcend this, most organizations end up rewarding people who are good at acquiring power, which poisons the culture, destroys trust and makes most people within those organizations a bit nauseous.

Working on my own, those dynamics are non-existent. The energy wasted on that drama can be re purposed to all sorts of positive activities in my life, including ironically helping people recover their sanity from within those toxic cultures.

#5 Detaching from the self-importance of career and embracing vulnerability

For the longest time, I identified as a successful professional who worked for good companies and went to good schools. That was the problem.

Today’s knowledge economy, once you’ve gained access, has almost no downside. You can go from job to job and even if you “fail” you’ll probably still get a higher salary in a new job. Facing vulnerability or uncertainty is to be feared, but rarely experienced.

Working on my own means an almost constant sense of fear, uncertainty and vulnerability. If I ran from vulnerability, I could not make this work. Within that vulnerability, I have had to dance with my fears and take action regardless. Doing so has made me feel much more alive than at any moment in any previous jobs.

Brene Brown shares her wisdom on vulnerability with us by pointing out, “Vulnerability is the birthplace of innovation, creativity and change.”

While creating and sharing in public is scary, it has had the counterintuitive outcome of making me realize that I am in fact, not that special and that perhaps I have tapped into a courage I did not know I had before.

#6 Instant connection & camaraderie

by Aaron Burden on Unsplash

Without a team or office to go to every day, I’ve had to purposefully start cultivating relationships and connections. The best way I’ve found to connect with people is to share my story, both through writing and in-person connections.

When I share my story and what I’m passionate about, I often here an offer “you have to meet X!”

At a conference in New York, someone I had met connected me to another self-employed soul working on many of the same things as me. That connection started with an enthusiastic video call, but quickly moved into a real-life friendship and hopefully future collaboration. This process has happened over and over again. Many people underestimate how many people are out there in the world who may be on a similar journey.

When you combine mission with the shared experience and vulnerability of being self-employed, I’ve found it often turns connections into meaningful friendships in no time.

#7 Being able to “ramp down” my paid work

Being self-employed, the money shows up after you complete work or projects. This can be much less consistent or predictable than full-time employment. Here is what my income looks like over the past fifteen months:


Some of this inconsistency is by design. Over the past year, I took two one-month trips to test out extended travel. One trip was completely without any work and one I was able to take while doing some remote work.

In months 10 and 11, I said no to all incoming work because I wanted to work on my podcast and launch the future of work mindset assessment that I had been building. Neither were projects designed to make money, but burning ideas that I needed to create to feed my passion.

Being able to “ramp down” your work is a huge feature of being self-employed not available to many full-time workers. To take a leave of absence or unpaid leave is a sign of failure. This is why so many people often “burn out.”

Working on my own, I can take time to recharge, spend time with family or focus on projects that I’m excited by to make the journey a lot more sustainable. My goal for this summer is to spend 50 days working or not working remotely hanging with my grandmother and family at the family lake house. This would be almost impossible if I were working in a traditional full-time job, but quite easy with the ability to ramp down my work and push for more remote opportunities.

#8 Re-framing money

Photo by NeONBRAND 

A steady job meant my income on autopilot. Paychecks showed up in my bank account no matter what. Since I was lucky to have jobs that paid me much more than I needed, it led to a certain recklessness and willingness to pay for convenience because much of my time was spent at said full-time job. $300 for an Acela train to Boston to save 45 minute? Done. $75 dinners? Why not?

My relationship to money has flipped. Periods of unpaid work are not a failure, but valuable space to let my creative energy run wild. After all, this journey is a long-term committment.

I’ve also lost a lot of interest in expensive things and experiences. The more I spend, the less creative space I’ll have in my life. There are some things I still splurge on, but I’m much more intentional about what I really need and have embraced a minimalism and “don’t buy it” mentality with most things.

This led me to create a tool for other self-employed people to understand the relationship between how much work they need to do and the cost of their lifestyle (freelance target income calculator).

#9 Unlocking creative energy

It took about six months after leaving the corporate world for my creative spirit to awaken. While I had worked in an industry which does encourage some creativity, large organizations always have at least one person around who will spend more time poking holes in your creations than sitting with you to dream. Risk-management will always win over new ideas in most companies.

Combining responsibility for my own life (in terms of making money to meet my basic needs), no one to question my ideas and intentional downtime or space to let my mind wander, I’ve found my mind flooded with half-baked ideas to experiment with and put into the world.

My rule of thumb has been to take action once two un-related people push me in a certain direction. This framework led me to launching a podcast, attending a conference of unconventional thinkers in Portland and launching my own digital learning experiment/academy despite my fear and uncertainty.

A strong current of creative energy can easily overcome fear to help turn half-baked ideas into things that make a difference. Some people will never give themselves permission to have space in their time to ever let that creative energy appear.

#10 Healing & becoming a nicer person

Photo by Matheus Ferrero on Unsplash

I wouldn’t claim I am Mother Teresa, but relative to the person I was in the corporate world, I find myself being more patient, kind and generous to the people around me. The marginal blows of insanity and negativity in the corporate world slowly eat away at you in a way that is hard to put a finger on, but easy to spot once you get a bit of distance.

Having ownership of my own time, creations, and work enables me to take responsibility for the person I am being in the world at all time, without the opportunity to place blame on anyone else. In addition, it also gives me the freedom to say no to any projects or situations where I would be working with or spending time with people who are good at draining my energy (I like to call these people energy vampires).

Deep down I always had a fear that a long corporate career would be a death by a thousand blows, slowly destroying the person I wanted to be without me realizing it.

It took me almost eleven years to gain the courage to carve my own path, but I now see a path in the world where I have some confidence that I can be who I want to be in the world.

About Paul Millerd

Paul is a writer, creator, and curious human that is passionate about how people can reimagine their relationship with work to do things that matter. He published The Pathless Path in 2022.

Leave a Comment