We love round numbers, don't we? $100,000 is a frequent freelancing milestone. You feel like six figures means you're doing something properly.

You've most likely already conquered initial freelancing challenges like finding clients, setting fair pricing, coping with criticism, getting through dry spells, managing funds, etc.

You think I must be doing well. Last month, my freelance income topped $100,000.

That may not sound impressive considering I've been freelancing for 2.75 years, but I made 30% of that in the previous four months, which is crazy.

Here are the things I wish I'd known during the early days of self-employment that would have helped me hit $100,000 faster.

1. The Volatility of Freelancing Will Stabilize.

Freelancing is risky. No surprise.

Here's an example.

October 2020 was my best month, earning $7,150. Between $4,004 in September and $1,730 in November. Unsteady.

Freelancing is regrettably like that. Moving clients. Content requirements change. Allocating so much time to personal pursuits wasn't smart, but yet.

Stabilizing income takes time. Consider my rolling three-month average income since I started freelancing. My three-month average monthly income. In February, this metric topped $5,000. Now, it's in the mid-$7,000s, but it took a while to get there.

Finding freelance gigs that provide high pay, high volume, and recurring revenue is difficult. But it's not impossible.

TLDR: Don't expect a steady income increase at first. Be patient.

2. You Have More Value Than You Realize.

Writing is difficult. Assembling words, communicating a message, and provoking action are a puzzle.

People are willing to pay you for it because they can't do what you do or don't have enough time.

Keeping that in mind can have huge commercial repercussions.

When talking to clients, don't tiptoe. You can ignore ridiculous deadlines. You don't have to take unmanageable work.

You solve an issue, so make sure you get rightly paid.

TLDR: Frame services as problem-solutions. This will let you charge more and set boundaries.

3. Increase Your Prices.

I studied hard before freelancing. I read articles and watched videos about writing businesses.

I didn't want to work for pennies. Despite this clarity, I had no real strategy to raise my rates.

I then luckily stumbled into higher-paying work. We discussed fees and hours with a friend who launched a consulting business. It's subjective and speculative because value isn't standardized. One company may laugh at your charges. If your solution helps them create a solid ROI, another client may pay $200 per hour.

When he told me he charged his first client $125 per hour, I thought, Why not?

A new-ish client wanted to discuss a huge forthcoming project, so I raised my rates. They knew my worth, so they didn't blink when I handed them my new number.

TLDR: Increase rates periodically (e.g., every 6 or 12 months). Writing skill develops with practice. You'll gain value over time.

4. Remember Your Limits.

If you can squeeze additional time into a day, let me know. I can't manipulate time yet.

We all have time and economic limits. You could theoretically keep boosting rates, but your prospect pool diminishes. Outsourcing and establishing extra revenue sources might boost monthly revenues.

I've devoted a lot of time to side projects (hopefully extra cash sources), but I've only just started outsourcing. I wish I'd tried this earlier.

If you can discover good freelancers, you can grow your firm without sacrificing time.

TLDR: Expand your writing network immediately. You'll meet freelancers who understand your daily grind and locate reference sources.

5. Every Action You Take Involves an Investment. Be Certain to Select Correctly.

Investing in stocks or crypto requires paying money, right?

In business, time is your currency (and maybe money too). Your daily habits define your future. If you spend time collecting software customers and compiling content in the space, you'll end up with both. So be sure.

I only spend around 50% of my time on client work, therefore it's taken me nearly three years to earn $100,000. I spend the remainder of my time on personal projects including a freelance book, an investment newsletter, and this blog.

Why? I don't want to rely on client work forever. So, I'm working on projects that could pay off later and help me live a more fulfilling life.

TLDR: Consider the long-term impact of your time commitments, and don't overextend. You can only make so many "investments" in a given time.

6. LinkedIn Is an Endless Mine of Gold. Use It.

Why didn't I use LinkedIn earlier?

I designed a LinkedIn inbound lead strategy that generates 12 leads a month and a few high-quality offers. As a result, I've turned down good gigs. Wish I'd begun earlier.

If you want to create a freelance business, prioritize LinkedIn. Too many freelancers ignore this site, missing out on high-paying clients. Build your profile, post often, and interact.

TLDR: Study LinkedIn's top creators. Once you understand their audiences, start posting and participating daily.

For 99% of People, Freelancing is Not a Get-Rich-Quick Scheme.

Here's a list of things I wish I'd known when I started freelancing.

1. Although it is erratic, freelancing eventually becomes stable.

2. You deserve respect and discretion over how you conduct business because you have solved an issue.

3. Increase your charges rather than undervaluing yourself. If necessary, add a reminder to your calendar. Your worth grows with time.

4. In order to grow your firm, outsource jobs. After that, you can work on the things that are most important to you.

5. Take into account how your present time commitments may affect the future. It will assist in putting things into perspective and determining whether what you are doing is indeed worthwhile.

6. Participate on LinkedIn. You'll get better jobs as a result.

If I could give my old self (and other freelancers) one bit of advice, it's this:

Despite appearances, you're making progress.

Each job. Tweets. Newsletters. Progress. It's simpler to see retroactively than in the moment.

Consistent, intentional work pays off. No good comes from doing nothing. You must set goals, divide them into time-based targets, and then optimize your calendar.

Then you'll understand you're doing well.

Want to learn more? I’ll teach you.

If asked, run.

An entrepreneur asked me about her pitch deck. A Platform as a Service (PaaS).

She told me she hadn't done her 5-year forecasts but would soon.

I said, Don't bother. I added "time-wasting."

“I've been asked”, she said.

“Who asked?”

“a VC”

“5-year forecast?”

“Yes”

“Get another VC. If he asks, it's because he doesn't understand your solution or to waste your time.”

Some VCs are lagging. They're still using steam engines.

10-years ago, 5-year forecasts were requested.

Since then, we've adopted a 3-year plan.

But It's outdated.

Max one year.

What has happened?

Revolutionary technology. NO-CODE.

Revolution's consequences?

Product viability tests are shorter. Hugely. SaaS and PaaS.

Let me explain:

• Building a minimum viable product (MVP) that works only takes a few months.

• 1 to 2 months for practical testing.

• Your company plan can be validated or rejected in 4 months as a consequence.

After validation, you can ask for VC money. Even while a prototype can generate revenue, you may not require any.

Good VCs won't ask for a 3-year business plan in that instance.

One-year, though.

If you want, establish a three-year plan, but realize that the second year will be different.

You may have changed your business model by then.

A VC isn't interested in a three-year business plan because your solution may change.

Your ability to create revenue will be key.

• But also, to pivot.

• They will be interested in your value proposition.

• They will want to know what differentiates you from other competitors and why people will buy your product over another.

• What will interest them is your resilience, your ability to bounce back.

• Not to mention your mindset. The fact that you won’t get discouraged at the slightest setback.

• The grit you have when facing adversity, as challenges will surely mark your journey.

• The authenticity of your approach. They’ll want to know that you’re not just in it for the money, let alone to show off.

• The fact that you put your guts into it and that you are passionate about it. Because entrepreneurship is a leap of faith, a leap into the void.

• They’ll want to make sure you are prepared for it because it’s not going to be a walk in the park.

• They’ll want to know your background and why you got into it.

• They’ll also want to know your family history.

• And what you’re like in real life.

So a 5-year plan…. You can bet they won’t give a damn. Like their first pair of shoes.

Consider yourself lucky if your last FAANG interview was rejected.

FAANG—Facebook, Apple, Amazon, Netflix, Google

(I know its manga now, but watch me not care)

These big companies offer many benefits.

1. large salaries and benefits

2. Prestige

3. high expectations for both you and your coworkers.

However, these jobs may have major drawbacks that only become apparent when you're thrown to the wolves, so it's up to you whether you see them as drawbacks or opportunities.

I know most college graduates start working at big tech companies because of their perceived coolness.

I've worked in these companies for years and can tell you what to expect if you get a job here.

Little fish in a vast ocean

The most obvious. Most billion/trillion-dollar companies employ thousands.

You may work on a small, unnoticed product part.

Directors and higher will sometimes make you redo projects they didn't communicate well without respecting your time, talent, or will to work on trivial stuff that doesn't move company needles.

Peers will only say, "Someone has to take out the trash," even though you know company resources are being wasted.

The power imbalance is frustrating.

What you can do about it

Know your WHY. Consider long-term priorities. Though riskier, I stayed in customer-facing teams because I loved building user-facing products.

This increased my impact. However, if you enjoy helping coworkers build products, you may be better suited for an internal team.

I told the Directors and Vice Presidents that their actions could waste Engineering time, even though it was unpopular. Some were receptive, some not.

I kept having tough conversations because they were good for me and the company.

However, some of my coworkers praised my candor but said they'd rather follow the boss.

An outdated piece of technology can take years to update.

Apple introduced Swift for iOS development in 2014. Most large tech companies adopted the new language after five years.

This is frustrating if you want to learn new skills and increase your market value.

Knowing that my lack of Swift practice could hurt me if I changed jobs made writing verbose Objective C painful.

What you can do about it

1. Work on the new technology in side projects; one engineer rewrote the Lyft app in Swift over the course of a weekend and promoted its adoption throughout the entire organization.

2. To integrate new technologies and determine how to combine legacy and modern code, suggest minor changes to the existing codebase.

Most managers spend their entire day in consecutive meetings.

After their last meeting, the last thing they want is another meeting to discuss your career goals.

Sometimes a manager has 15-20 reports, making it hard to communicate your impact.

Misunderstandings and stress can result.

Especially when the manager should focus on selfish parts of the team. Success won't concern them.

What you can do about it

1. Tell your manager that you are a self-starter and that you will pro-actively update them on your progress, especially if they aren't present at the meetings you regularly attend.

2. Keep being proactive and look for mentorship elsewhere if you believe your boss doesn't have enough time to work on your career goals.

3. Alternately, look for a team where the manager has more authority to assist you in making career decisions.

After a certain point, company loyalty can become quite harmful.

Because big tech companies create brand loyalty, too many colleagues stayed in unhealthy environments.

When you work for a well-known company and strangers compliment you, it's fun to tell your friends.

Work defines you. This can make you stay too long even though your career isn't progressing and you're unhappy.

Google may become your surname.

Workplaces are not families.

If you're unhappy, don't stay just because they gave you the paycheck to buy your first home and make you feel like you owe your life to them.

Many employees stayed too long. Though depressed and suicidal.

What you can do about it

1. Your life is not worth a company.

2. Do you want your job title and workplace to be listed on your gravestone? If not, leave if conditions deteriorate.

3. Recognize that change can be challenging. It's difficult to leave a job you've held for a number of years.

4. Ask those who have experienced this change how they handled it.

You still have a bright future if you were rejected from FAANG interviews.

Rejections only lead to amazing opportunities. If you're young and childless, work for a startup.

Companies may pay more than FAANGs. Do your research.

Ask recruiters and hiring managers tough questions about how the company and teams prioritize respectful working hours and boundaries for workers.

I know many 15-year-olds who have a lifelong dream of working at Google, and it saddens me that they're chasing a name on their resume instead of excellence.

This article is not meant to discourage you from working at these companies, but to share my experience about what HR/managers will never mention in interviews.

Read both sides before signing the big offer letter.

WTF is wrong with you people?

When I was laid off as editor of my town's daily newspaper, I went silent on social media. I knew it was coming and had been quietly removing personal items each day, but the pain was intense.

I posted a day later. I didn't bad-mouth GateHouse Media but expressed my sadness at leaving the newspaper industry, pride in my accomplishments, and hope for success in another industry.

Normal job-loss response.

What do you recognize as abnormal?

The bullshit I’ve been reading from laid-off folks on LinkedIn.

If you're there, you know. Many Twitter or Facebook/Meta employees recently lost their jobs.

Well, many of them did not “lose their job,” actually. They were “impacted by the layoffs” at their former employer. I keep seeing that phrase.

Why don’t they want to actually say it? Why the euphemism?

Many are excited about the opportunities ahead. The jobless deny being sad.

They're ecstatic! They have big plans.

Hope so. Sincerely! Being laid off stinks, especially if, like me, your skills are obsolete. It's worse if, like me, you're too old to start a new career. Ageism exists despite denials.

Nowadays, professionalism seems to demand psychotic levels of fake optimism.

Why? Life is unpredictable. That's indisputable. You shouldn't constantly complain or cry in public, but you also shouldn't pretend everything's great.

It makes you look psychotic, not positive. It's like saying at work:

“I was impacted by the death of my spouse of 20 years this week, and many of you have reached out to me, expressing your sympathy. However, I’m choosing to remember the amazing things we shared. I feel confident that there is another marriage out there for me, and after taking a quiet weekend trip to reset myself, I’ll be out there looking for the next great marital adventure! #staypositive #available #opentolove

Also:

“Now looking for our next #dreamhome after our entire neighborhood was demolished by a wildfire last night. We feel so lucky to have lived near so many amazing and inspirational neighbors, all of whom we will miss as we go on our next housing adventure. The best house for us is yet to come! If you have a great neighborhood you’d recommend, please feel free to reach out and touch base with us! #newhouse #newneighborhood #newlife

Admit it. That’s creepy.

The constant optimism makes me feel sick to my stomach.

Viscerally.

I hate fakes.

Imagine a fake wood grain desk. Wouldn't it be better if the designer accepted that it's plastic and went with that?

Real is better but not always nice. When something isn't nice, you don't have to go into detail, but you also shouldn't pretend it's great.

How to announce your job loss to the world.

Do not pretend to be happy, but don't cry and drink vodka all afternoon.

Say you loved your job, and that you're looking for new opportunities.

Yes, if you'll miss your coworkers. Otherwise, don't badmouth. No bridge-burning!

Please specify the job you want. You may want to pivot.

Alternatively, try this.

You could always flame out.

If you've pushed yourself too far into toxic positivity, you may be ready to burn it all down. If so, make it worthwhile by writing something like this:

Well, I was shitcanned by the losers at #Acme today. That bitch Linda in HR threw me under the bus just because she saw that one of my “friends” tagged me in some beach pics on social media after I called in sick with Covid. The good thing is I will no longer have to watch my ass around that #asspincher Ron in accounting, but I’m sad that I will no longer have a cushy job with high pay or access to the primo office supplies I’ve been sneaking home for the last five years. (Those gel pens were the best!) I am going to be taking some time off to enjoy my unemployment and hammer down shots of Jägermeister but in about five months I’ll be looking for anything easy with high pay and great benefits. Reach out if you can help! #officesupplies #unemploymentrocks #drinkinglikeagirlboss #acmesucks

It beats the fake positivity.