The Low-Risk Path to Resign From Your Job and Start Earning $100K Per Year

The Low-Risk Path to Resign From Your Job and Start Earning 0K Per Year

How to increase your income, win back your time and become a business owner

The Low-Risk Path to Resign From Your Job and Start Earning 0K Per Year
Image: Unsplash

Controversial opinion: You don’t have to start a world-changing business to be a successful entrepreneur.

Trying to tackle a business idea that is truly world-changing is a very likely path to failure as an entrepreneur, especially if it’s one of the first businesses you start.

There’s a much lower-risk path to becoming a business owner that isn’t glamourized by the media but still gives you all the perks of being your own boss:

  • Increased earnings,
  • Freedom to do with your time what you want,
  • A gateway to bigger wealth.

In this post, I will walk you through that process so you can hopefully do it yourself.

The immediate aim is to allow you to resign from your job ASAP.

Here’s how we’re going to do it, in brief:

  1. Choose a skill to become an expert in.
  2. Dedicate as much time per day as possible to become better at the skill than most people. 2 hours per day for two months will probably get you there.
  3. Start building a reputation on a freelancing platform. Pick up entry-level odd-jobs related to your skill that are project-based or part-time. The sooner, the better. Learn from mistakes, and improve your skill level.
  4. When you’ve got enough work to cover your current salary, resign.
  5. Build a team of contractors to outsource menial work to, using your expertise to do planning and quality control. Go from freelancer to agency!
  6. Pay attention to repeated product requests and trends, and then create a small product that you can build once and sell many times.

I started my professional life as an employee at a fintech company.

After a while, I grew frustrated that I was building someone else’s business and was getting underpaid for the value I created.

I started freelancing using a skill I had learned at work, but also on weekends — Bubble. My hourly rate on Upwork started at $8. I even built an RSS feed monitor for Upwork, so I would get notifications every time a new job was posted with the word “bubble” in the title.

My first job was creating a simple social-media-style contest for someone. They paid me $200. I probably put ±40 hours of work into it. Grossly underpaid. But that’s how I started.

For three months, I held down two jobs while freelancing alongside my normal job. I quickly built a reputation and bumped my hourly rate to around $30/hr. I remember the day the first Upwork payment came through that was more than my normal salary.

A big day for me… freelance work out-earned my full-time salary

It was the day I knew I was going to quit.

I gave my notice, and took the plunge!

For a few months, I operated in a quasi-freelance-agency state where I was trying to build up capacity to take on more work while also keeping the cash coming in. Being able to charge out my time at a significant hourly rate meant I could start working half my time on agency ops, half on cash, and then that ratio slowly decreased.

I’m not at the stage where our agency is still running, and I’m working on developing a product (step 6).


Most people resign first, then try to determine what to do next. In most cases, it’ll end with you back in the job market. Not what we want.

What you need to do instead is choose a high-leverage skill to become better at than most people.

Here are some tips:

  1. Pick something you’re interested in. You’ll be working on this (mostly) after hours. Having an interest means you’ll be more inclined to work at it.
  2. Pick something you’re naturally good at. If you have a talent for the thing you’re learning, it’ll mean you’re already naturally better at it than most people and your learning/experience curve will be sharper.
  3. Go specific. You might be tempted to pick something like “marketing” or “sales”. Don’t. Choose an industry to specialize in if possible. Example: “B2B marketing in insurance”.
  4. Pick something aligned to your current job or where you have the most previous experience. Unless you really hate your current work and want to completely remove yourself from the industry, I’d advise you to stick to the market you know. Experience counts for a lot. By changing industry, you’re almost giving up all the hard work you’ve already put in.
  5. Choose something in demand. Example: As AI writing tools become prolific, I’d be reluctant to become a content writer. There’s very little that can set your blog post apart from an AI-generated piece of content unless you’re a subject-matter expert. On the other hand, YouTube SEO is becoming super popular as content generation shifts from text to video. Pick a growing niche where there’s lots of demand for your skills.

Still not sure? The next step might help.

Go on to Upwork, Fiverr, or Take your pick. Browse as if you are trying to find a freelancer. Go to your industry or browse a few categories you’re interested in. If you had a few options after looking at the tips above, use this to try and eliminate options.

What are you looking for?

  1. Demand. Check how many people there are looking for what you’re thinking about learning about.
  2. Hourly rate/project budget. Check what people are paying for it. Steer away from anything where the hourly rate <$10 consistently.

Note: Don’t be discouraged by competition as you do this. Firstly, most people on these platforms are not good; they’re either re-selling services or not delivering a great service. It does not take a lot to get to the top. Secondly, the fact that there is competition is good. It validates that there is demand for your skill.

That’s the hardest part of this whole process!

Find the best resources to learn about your particular skill. Here are some good places to look:

  1. YouTube — The ultimate gold mine of info. You can literally learn anything here for free.
  2. Udemy — An affordable place to find useful courses.
  3. Substack — Find the most popular newsletters on your topic and subscribe.
  4. Content Creators — Do some googling and find your best blogs and sites on the topic. Bookmark them and subscribe to any newsletters.

Learning is not only about picking up the skill, you want to start living in that world, too. Visit online communities, Discords, forums etc. Get a feel for the way that “world” operates.

Tip: Dedicate specific slots during your week where you are only going to be learning. During those times, hide your phone away and put your head down. If you’re serious about quitting your job, you should view these as “non-negotiables”.

Don’t get stuck in the imposter syndrome stage!

The worst thing you can do for your progress is to think “I just don’t know enough yet”.

The truth is, you’ll never know enough and the imposter feeling never goes away. Learning is a journey without an ending.

If you feel like this might be you, then set a hard deadline for your “learning” journey to end. Everything else you need to know will come on the job.

Possibly the most daunting part of the journey for most people… how do you get your first sales?

You’re now at the stage of your journey where you’re becoming a freelancer.

The good news: It’s never been easier to find your first clients.

Platforms like Upwork, Fiverr and make it easier than ever. Sure, they have their downsides. But the opportunity they offer in terms of access to a pool of paying clients far outweighs the cons for any person starting out.

First, get set up. A bit of advice based on my experience: Put your rates super low. Normally, I wouldn’t suggest getting into a “race to the bottom” in pricing, but with no reviews or reputation on the platform, you have to start low enough that the risk for the client is almost null.

When you’re bidding for new contracts: Go above and beyond.

Here are the keys to success:

  1. Speed. The number one thing that will get you noticed is if you’re in the top 5 applicants. If you have a low platform reputation (< 3 reviews) and aren’t among the first to apply, your application is as good as gone. You’ll never get chosen.
  2. Address why you have no reputation on the platform. “I’ve just got started as a freelancer but have years of experience in this field outside of the platform.
  3. Show you are willing to do the work before getting paid. Do as much preparation for the contract as possible. Illustrate your knowledge.
  4. Write in short, sharp sentences. Illustrate why you’re a good fit.
  5. Start small. Your ideal jobs to look for are entry-level odd-jobs. These are the ones that clients are more likely to take a risk with a “noob” on.
  6. Send relevant portfolio links (if you have them) that are applicable. (This is where the “learn by doing” step above comes in handy. If you’ve done that, you’ll at least have a small portfolio of projects you can show)
  7. Open yourself up for a 15-minute call. Let the potential client know you’re happy to chat with them to iron out any concerns.
  8. Make a no-brainer offer. Offer a 100% money-back guarantee if the client is unsatisfied with your work. Or unlimited revisions. If you can make your offer so good that they’d be stupid not to accept it, you will likely win the contract.
  9. Use your network. Ask friends, family and work colleagues who might want your services to hire you on the platform. Deliver the work at a discount, and ask them to leave a review.

Now, you’ve done absolutely everything you can. There’s only one thing left to do:

Stay Persistent

When you’re just starting, getting a bunch of rejections is normal.

Don’t let that get you down. Stick with your applications and keep submitting them.

You will land a job if you submit 100 contract proposals using the principles above.

If you don’t, you can email me for a free consultation where we can run through your profile and how you’re making offers.


When you start winning contracts, make sure you are continuously over-delivering.

This does two things:

  1. Builds your reputation on the platform, and
  2. Wins you repeat work with your current clients.

When (the time will come) you find yourself getting stretched, you should narrow your job search down and only start applying for jobs that are worth your while.

Apply all the same principles above, and continue to build up your reputation.

Pay Attention to What the Market Wants

This should also be a period where you constantly pay attention to what people want from your niche.

Pick up on:

  • Repeated requests,
  • The jobs with the highest budgets,
  • The urgency of the jobs posted.

You’re starting to do your market research phase. After that, things are about to get serious!

When you are confident in your ability to:

  1. Win new work,
  2. Deliver on that work, and finally,
  3. When your hourly rate is equivalent to what you’re earning at your full-time job.

It’s time to decide to resign from your job.

Tip: When you resign, consider whether your current employer might be a potential client for your services. This might be a way to de-risk the decision even further. Offer to sell your time back to your employer if they need your position filled.

At the end of this step, you want to get to this situation: You are selling your company’s time in return for an outcome or service delivered.

What the above sentence describes is an agency. You’ve become a service provider.

The main difference between where we are now and where we want to go? More capacity and slimmer margins.

If you’re anything like me, you will start to work harder and harder, and longer and longer hours, because the money is really good! What that meant was, I got stuck in a very comfortable rut. Because the money I was making was much more than I was used to, I stalled my progress. I was super happy with my situation.

First — that is completely fine.

You’re going through a massive change in your professional life; it’s okay to mentally “take it easy” for a little while.

Second — don’t let that become the norm.

Like the learning stage of this process, it helps to set a deadline. Now though, that deadline might not be time-linked but cash-linked.

Here’s what I did:

  • I paid myself the same salary I was earning at my job. It covered my expenses, and I didn’t need more at that time of my life.
  • I put the rest of the money into a business bank account and started building up a cash balance.
  • I set myself the target of $100k. That would give me enough cushion to confidently make some mistakes on my journey to becoming an agency owner.

At $100k, it was time to start scaling up. That number might be different for you.

Here’s the process:

1: Find a list of potential contractors to work with.

Search places where you used to look for work.

Freelancers are always looking for work. Spin up a Typeform and post a link in forums where they hang out, saying you’re looking for reliable people to work with.

In my experience, these are the most important attributes to look for/test for when looking for contractors:

  • They read instructions carefully and can follow them.
  • They speak your language fluently. You cannot afford for instructions to be misinterpreted.
  • They communicate frequently. Unreliable communication
  • Trust your gut. If someone doesn’t feel trustworthy in your first interaction with them, they’re probably not. Steer clear.
  • Ask hard questions in your interview.

2: Start by giving your first potential contractors small chunks of work

You’re starting to almost be a Product Manager now. You take in instructions from clients and then convert them into a plan that you then hand off to workers to complete for you.

Tip: Don’t let your contractors charge you hourly. Give them the smallest deliverables possible, and provide budgets you are willing to pay for the tasks. I like to use Trello to manage this process.

Why? Hourly work incentivizes long deadlines. Task-based budgets incentivize fast work.

When you have someone consistently delivering, you can start handing over more responsibility and giving them bigger and bigger chunks of work to deliver.

Have a very rigid system for managing your contractors, the work you give them, and how they are expected to execute that work.

Here are things to consider:

  • Budget
  • Timeline
  • What the revision process looks like (when work is not delivered to standard)
  • What happens when they don’t deliver or deliver poor quality work

The clearer the instructions, the easier it is to be black and white in dealing with contractors. If it says “Complete 1, 2 and 3,” and they’ve only done 1 and 2 — you have recourse.

3: Remove yourself from operations

Once you’ve got a reliable team of contractors working with you, they’re going to hang around if these two things are maintained:

  1. They’re remunerated fairly, and
  2. There is a consistent stream of work.

There will be natural churn, but that is normal.

The next step is to start removing yourself from that whole process. You don’t want to be dealing with any of the actual operational side of your business.

This is a gradual process and one that might be a difficult step for you to take. But, it is necessary if you want to grow your business.

By removing yourself from the delivery of the end service/product, you will free up time to focus on the most important thing to building a big business: Finding new clients.

To remove yourself from operations, you’re likely going to need the following people in place:

PS: This is a list specifically for a technically-orientated agency (like mine).

  1. A team of contractors. They’re the ones executing all the work.
  2. A “solution architect”. This is someone who takes clients’ problems and breaks them down into actionable tasks for the contractors to work on. They build and plan the solution. This needs to be someone reliable and experienced.
  3. Your client manager. This will be someone who manages the interface with the clients and keeps them happy. Agency businesses need to have someone like this to be successful and win referrals (which is a strong growth driver for agencies).
  4. A project manager. Someone who ensures all the above three people execute what they need in time and deliver results according to the required deadlines.
  5. Ops. Someone to do the “grunt work” like paying staff, contracting, documentation, accounting etc. Virtual assistants are great for this.

Note: These don’t have to all be full-time roles. You can use freelancers to do all of these tasks. You will need to strike a balance between full-time employees, contractors on retainer and freelancers, depending on your specific situation and needs.

Tip: Incenticivize this team according to the outcomes you want from them. Example: Client managers are responsible for happy clients. Build a feedback loop to ensure they achieve that (like an NPS survey). Then, incentivize them using an improved/maintained NPS score.

4: Spend your time finding new clients

Now that your time is mostly freed up, you should be building and refining a repeatable sales process.

You’ll start by experimenting with yourself and getting to know exactly how to pitch and win new clients, but your goal is to build a repeatable system that other people can follow.

Once you think you’ve got there…

5: Build out a sales team

Time to ramp up growth!

This will come when everything else in your business is running smoothly and you’re confident that scaling up is not.

WARNING: Never hire a sales team until you are confident in your ability to deliver on the work they might bring in.

Sales teams are used to having their incentive packages very aligned to the sales they bring in. And you should structure their incentives the same way:

The majority of their income is generated on a profit-share model. More sales = more income.

If they are bringing in new leads and potential clients but you can’t deliver them because of any ops or capacity reason — you’re going to lose that sales team member really quickly.

And that’s not to mention the damage you’ll be doing to your reputation in the industry.

You’ve got a growing agency that’s largely running without your involvement — nice!

Your ultimate goal is to decouple your income from anyone’s time. Selling time for money is a good way to start a business, but it will never make you super wealthy. The margins are too slim, and the business is quite challenging to run.

The only way to decouple your income from time is to: Build Once, Sell Many Times.

You want to shift from selling services -> selling products.

And to do that, you need:

  1. A product to sell, or
  2. A way to productize your service.

But what products are we going to sell?

By now, you should have an excellent understanding of the industry you’re operating in.

You might start to notice patterns like:

  • People coming to you with the same problems over and over, or
  • People need things done in a certain way or timeframe.

If you spot patterns of problems — you’ve got a product to sell.

And fortunately, you’ve got a cash-generating business to launch it with!

This is a super exciting journey and one that is worthy of another post. But that’s for another day!

Go to Publisher:

Entrepreneur&#39;s Handbook – Medium

Author: Simon Huckk