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Just over three years ago I walked away from my 9 to 5 to start my own freelance business.

The uncertainty of what was next ended up being the fuel that I needed to get me from the first day to now – two years under my belt and I’m still alive to tell the tale.

When I first wrote this blog post, it was a year after I first cracked $250k in revenue. Since then, I’ve been figuring it out while helping others unlock their own potential to leave the 9 to 5 and start living their own dream. I’ve launched multiple companies (Crate, a software business + Hustle & Grind, an ecommerce site) while growing my consultancy to do work I could only dream of just a few years ago.

I’ve received a lot of love from friends, family and readers. I’ve also received a lot of questions about how I got to a place where I could leave my 9 to 5 and build a booming business in less than two years. In this blog post, I dive deep into some of the insights and tactics that helped me leave my job and launch a successful consulting business.

Whenever I’m asked that question,  I respond the same way every time:

Start hustlin’ while you still have your 9 to 5.

I’ve pulled together my top five tips for running a consulting gig while working the 9 to 5. These tips and tools will help any wantrepreneur get a little closer to making the leap and every hustler make a few extra dollars without compromising their existing job, their sanity or their social life.

1. Say “No” More than You Say “Yes”

I’ll be the first to admit, saying “no” is hard. But I also believe that saying “yes” too often can leave you over-committed and ineffective.

Saying “no” can make us feel weak, guilty and contradictory to achieving success. But those who say “no” more than they say “yes” are better able to focus on the important projects and client relationships that they’ve selected. They have more energy and produce better work. Their client relationships are generally stronger and their work-work-life balance is more easily managed.

FOMO (fear of missing out) is a powerful driver, but if you’re not careful it can get you get you into muddy waters. Whether drinks with friends or taking on projects that you’re not 100% sure will be worth your time or the client’s time, saying “yes” for the sake of FOMO is a dumb decision.

Lots of opportunities come up every week, but choosing the right ones is more important that choosing each one, even when you’re launching a business. Saying “no” more empowers you to make each decision count.

2. Make Your Processes Simple

Proposify - Software

The most effective way to succeed at running a consulting business while holding down a 9 to 5 is to plan for it.

Creating systems and processes that simplify your life and prevent things from getting out of control is critical to achieving long-term success and effectively managing both areas of your career.

The processes you put in place should help you improve efficiencies and increase earnings.

The key is to keep it simple. It shouldn’t require additional tasks, time or money. It should become part of your business and make your life easier. It should also add value to you and your clients.

There are many tools on the market that do just that. From accounting software like FreshBooks to proposal generating software like Proposify to help you streamline your proposal process and win more business.

Don’t reinvent your own wheel by doing the same thing multiple different times for each new client. Streamline your processes as much as you can, from creating and using email templates to tapping into Gmail’s Canned Response tool.

When you’re managing a full-time job and hustlin’ on the side, your time is extremely precious. These tactics and tools will streamline your processes, create extra time for focusing on new business, and ensure that your business transactions and interactions are professional from beginning to end.

3. Use Your Lunch Break for Client Calls

As much as we try to push the limits and search for more hours in the day, the reality is there are only 24 hours to go around. At least 8 of them are already earmarked for your 9 to 5 job. Your consulting business, unfortunately, gets whatever is left over.

It’s up to you to find creative ways to use the remaining hours in your day in the best possible way.

Consulting would be so much easier if everything we did was over the web. But in reality, you can’t manage a client relationship through email exclusively. Sure, you can find prospective businesses and clients online, get the email list of their CEOs, contact them and exchange a few emails… but at some point, you will have to pick up the phone and talk to them or meet with them face-to-face. Finding time to do this during normal business hours is a struggle we all face.

Fortunately, we get an hour for lunch every day. That’s one whole productive daylight hour that can be attributed to your consulting business and used for managing client relations, following up on project milestones, face-to-face meetings, and new client pitches. No matter what you need to talk about, your lunch hour is the perfect time to pick up the phone and make a call.

4. Hack Your Productivity with Apps & Tools

Increase your productivity with apps that simplify everything you do, from content management to your daily commute. There are many apps that, when used to their potential, can make your life so much easier.

Working for yourself while also working for others can be overwhelming at times. It can be confusing, tough and exhausting. Arm yourself with tools that position you for success and help you achieve results.

Schedule your emails in advance

Boomerang for Gmail lets you take control of when you send and receive email. With Boomerang you can write an email late at night or early in the morning and schedule it to send during business hours. You can also set reminders and follow-up notifications to keep you on your toes. This way, when your boss gets extra demanding, you don’t have to worry about forgetting to follow up with your own clients – your Boomerang has your back! Right Inbox is another great alternative worth checking out for email scheduling.

Manage your social media content with Hootsuite

When you’re busy running your own business and also working for someone else, the last thing you’re thinking about is getting in your daily tweets. I get it. That’s why Hootsuite is one tool you can’t live without. Whether you’re managing a number of client accounts or simply trying to keep up with your own, Hootsuite gives you the ability to schedule your content in advance, measure its performance and keep your content flowing.

UPDATE: I’d now recommend that you use Crate + Buffer.

Use Lyft or Uber to get around

Running back and forth between meetings is the worst time-sucker of all. Getting across town and back quickly and cheaply can be the difference between a good day and a stressful day. Save time and money with Lyft or Uber. If Uber is alive in your city, download the app today and say goodbye to flagging taxis and fighting the crowds for Metro.

Uber is a mobile app that gives you the power to request, ride, and pay for transportation via your mobile phone. It allows you to connect with a driver in a matter of minutes, choose your preferred route, and pay efficiently and automatically directly through the app. Even further, once you reach your destination, a detailed receipt is sent directly to your inbox in a matter of seconds making it even easier to track your business commutes when tax time rears its ugly head.

No matter how many clients and projects you’re managing through your consulting business, apps are a great way to hack your system and give you the control you need to crush every day!

5. Be Transparent With Your Clients

Honesty is the best policy and this 100% applies when you’re managing a job while running a consulting business. Your clients should have a clear picture of what to expect in terms of your commitment, your day job, and the hours that you’re available to receive calls and attend meetings. One effective way to manage client expectations and maintain transparency is by utilizing a client portal.

Setting real expectations not only ensures that you’re all on the same page, but it reduces stress on both you and the client, it keeps the relationship honest and transparent and doesn’t spook your boss because you’re not answering personal calls during business hours.

Wrapping Things Up

The past few years have been some of the best to date, but not without a lot of hard work, sweat, and coffee!

I hope these tips will give you the support you need to set the stones for your path to entrepreneurship or whatever greatness looks like to you. I hope you find value in the tips above and are able to embrace them into the world of entrepreneurship.


While it’s important to do all these little hacks and tricks… Nothing is more important than investing in yourself.

Read frequently. Collaborate often. Ask for advice. And HUNT for answers.

That’s what truly will differentiate you from the rest of the freelancers on the market and arm you with the better position when it’s time to put in your 2 weeks notice.

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Ross Simmonds

Ross Simmonds is a digital marketing strategist who has worked with everything from Fortune 500 companies to startups to drive results using digital marketing and technology.

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[…] Pricing is all about positioning and boundaries. Position yourself for higher rates (Leah Kalamakis wrote an article that will help you see this process in action), then say “No!” when people want you to work for less (Ross Simmonds helps you see why that’s valuable). […]

William C Murray
8 years ago

Awesome post as always Ross. Next coffee is on me!!

Jeremy Q. Butler
8 years ago

This is really good! I’m working on my consulting business now!

Ross Simmonds
8 years ago

Awesome Jeremy – Good luck with it! Any questions, lemme know.

Ross Simmonds
8 years ago

Good point around the job agreement. It’s definitely important that people look out for this or they could pay for it.

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7 years ago

I have 16 years fulltime experience in software development . I am not working now. Is is possible to become independent consultant. I know SEO as well. getting paying client is tough.

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