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Declan Wilson

4 Lessons I’ve Learned After Working for Myself for 2 Years

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Declan Wilson
Declan Wilson
Photo by Bench Accounting on Unsplash

I dreamed of working for myself since the day I entered corporate America.

The idea of working when I wanted, where I wanted, and how I wanted was so irresistible, I’d often spend countless hours at my boring office job scheming ways to bust out of there.

In the end I finally escaped the rat race of corporate America because, well, my wife graduated pharmacy school and got a job. (There’s a lot more to the story but that’s for another day.)

I have no regrets for my decision 2 years ago, but I’ve made a lot of preventable mistakes since. It’s my hope that I’ve learned from said mistakes and can pass on this knowledge to you (whom I’m assuming is me just like me from over 2 years ago).

My goal is to share with you 4 key lessons you should be well aware of before making the leap and working for yourself. If you already work for yourself, I hope this article will act as a refresher and maybe shift your paradigm (agh, sorry, I still haven’t shaken out all the corporate jargon from my lexicon).

Lesson 1: Freelancing is not a business

“For the vast majority of my adult life, I was a freelance writer, forever scrambling for work that paid an insulting non-amount.”
- Jen Sincero

I was blessed and cursed from the start.

After my final day of working in corporate America, I got home and hopped on the phone with a prospect. By the end of the call I had my first client of my self-employment adventures.

“This is so easy,” I thought.


I spent the first 6 months of my self-employment tenure on this one, single project. Yes, this client and project injected some early much-needed cash for my business. But you know how they say Don’t keep all your eggs in one basket? Well this was my one egg, and only basket.

You can guess the outcome.

After 6 months they shut the project down.

I had no prospects. No leads. Nothing.

I realized something important:

Freelancing is not a business — it’s nothing more than a glorified job. (But hey, at least you get to work in coffee shops instead of cubicles.)

If you ever intend to set out on your own, freelancing is a great start…while you’re still employed.

This is the first mistake I made. I left steady cash flow for irregular cash flow which ultimately meant one thing: chasing the buck.

While you still have a steady job, avoid the stress of finding cash flow by freelancing odds and end jobs. Take on a variety of projects to understand the skills you have (and more importantly don’t have). Use this time to study your ideal client, what services they want, what pricing is best for them (and you). I can’t tell you how difficult it is to study and focus on the business you want to eventually build when you are desperately trying to find any paying client.

In the end, if you leave your job only to become a freelancer you’ll quickly realize you’re in the same spot.

Lesson 2: Find your people

“To all the other dreamers out there, don’t ever stop or let the world’s negativity disenchant you or your spirit. If you surround yourself with love and the right people, anything is possible.”
- Adam Green

Working for yourself is a lonely venture. You face rejection more often than acceptance, you work weird hours, you feel isolated from your closest friends and family because they just don’t understand. While I highly suggest you still have an emotional support system around you of friends and family, make it a priority to intentionally build a support group of people in a similar situation as you.

Not to bash the 9-to-5er’s, but most people aren’t going to know what you are going through and offer support that’s helpful and encouraging (or when necessary, lay down some harsh truths).

Early on — before I even left my full-time job — I had a small group of friends who had similar ambitions of setting out and doing their own thing. We’d hop on a weekly group call, set goals, offer advice, and keep each other accountable.

Todd, Kyle, and Alexander have helped me navigate some of the toughest months of working for myself (aka the months I couldn’t pay myself), because they’ve gone through similar struggles and know what works and what doesn’t.

Even now, three years later we meet up every Friday for one hour, an hour that is vital and necessary because they are my people.

“But how do I go out and find other employed people like me?” You may be asking.

I can’t give you advice on how to meet people. I’m probably the worst at it. But here’s what I can suggest: share your stories, your struggles, and your experiences.

I met Todd here on Medium. I met Alex through Todd who first connected on Twitter. And I introduced Kyle to the group after emailing a blogger who I followed (Kyle worked for him at the time and responded, the rest is history). Funny enough, I’ve only met Todd and Kyle once in real life, and Alex zero times and I consider these guys some of my closest friends.

Eventually, people will find you simply because they resonate with what you are going through. And if you find other people who are sharing their stories, reach out, offer to help.

This isn’t a zero-sum game.

Lesson 3: Have a runway (I didn’t follow this)

“A simple fact that is hard to learn is that the time to save money is when you have some.”
- Joe Moore

As a general rule of thumb, I’ve heard you should have at least 3 months of income saved up in case you ever want to quit your job.

After following this advice I can confidently suggest quadrupling that total. Heck, save 15-18 months of income before jumping off the 9-to-5 train.

You’re probably shaking your head in disbelief. 15-18 months of income is not something you can scrounge together by digging through the couch cushions or sticking to your Target shopping list. It takes a lot of sacrifice and a lot of time to save up, time you think is better spent building your business.

I’ll dive more into this in the next lesson, but here’s the hard truth:

If you launch your self-employment venture with out a substantial runway saved up, you will struggle.

It’s hard to build a business on your own. It’s hard to get clients to pay for your work or customers to buy your product. It’s hard to pay yourself. Money is the goal but it’s also a distraction. When you don’t have enough of it you take shortcuts, you find less than ideal clients, you say ‘Yes’ to things that should be a ‘No.’

I was once so strapped for cash that I took on a client for 1/3 of what I was previously charging other clients. After our discovery call I had this inkling of a feeling to walk away from the sale. Something told me this project wasn’t worth it. But I needed the money.

Months later, after a stressful project and relationship I sent him what I thought was a final version of his website to take live. He didn’t think so:

I don’t know what state of consciousness you’re in but you have not effected even half of the changes we last discussed on the telephone. I don’t know if you lost the notes, but you’d better put the baby down and get your head in the game.

After receiving that email I spiraled into the lowest point of my self-employment adventure. I stopped looking for more clients. My business racked up debt. It was bad. I left my full-time job to build my own business and spend more time with my kids, so yeah, those words hurt. Those words hurt then and they hurt now.

If I had some initial money to invest in myself, to help me float during those inevitable dry months, who knows, maybe I’d have a different business at this point. Maybe I wouldn’t be so insecure about being a stay-at-home dad.

All I can say is this, saving 15–18 months of income is hard, but it’s not as hard as the alternative.

Lesson 4: Keep your job and the steady paycheck for as long as possible

“I was frustrated because I couldn’t get going, as I was trying to figure out how to make films. I had various jobs, I taught a SAT class, I was a bartender, I had a day job at an office and was making short films.”
- David O. Russell

This final lesson flies in the face of all the entrepreneur advice you’ll read on the internet:

Keep your day job.

I can’t go back in time and change my decision to leave my job in June of 2017. Honestly, I probably would do the same since the extra time I’ve been able to spend with my kids has been invaluable. But that decision has come at a cost.

  • I’m more anxious that I’ve ever been
  • I’m more tired than I’ve ever been
  • I’m more cynical than I’ve ever been

In other words, these past two years have changed me. I used to think the key to happiness was cutting loose the chains of a desk job to free yourself to follow your passions. I now know how far from the truth that is.

A day job supplies you with a consistent paycheck, health insurance (hopefully), people with whom to interact, and a training ground in business. When done properly, a day job can prep you for your future as a self-employed person.

And if you are single without kids, you have more than enough time (and energy) to build your business on the side.

Sure, it’s not as sexy as all the entrepreneurial stories you read online about founders sleeping on friends’ couches or launching a business in a garage, but it’s smart. It might seem like the market rewards those who are brave and take risks — and maybe part of that is true — however, the market will reward those who are smart and find creative ways to add value to the world.


As much as I hope this article helped you, I understand everyone’s situation is different. It’s hard to distill two years of self-employment experiences into four simple lessons, and honestly, I’m discovering new lessons every day. Even after two years I still feel like I’m only getting started.