For a decade, from 14-24, I worked at a fast-growing software company. Yes, you read that right—14. But that’s a story for another time. In March of 2020, I called it quits and started Datos Marketing.

While I had many years of great work-life balance and raved about working at my old job, it started to go downhill as I gained more responsibility and leadership changed.

My career trajectory:

• Data entry/validation – A few months
• Spanish marketing assistant – 5 years
• Junior email marketing – 2 years
• Mobile marketing manager – 1.5 years (started getting stressful)
• Demand manager/senior email marketing – 2 years (joy in work = gone)

I only hung on to the job because I loved the people I worked with and I was starting to get paid well. Plus, I had a fairly flexible schedule and I was able to work on some side projects.

But over time, my skillset had far surpassed the positions I was able to get in a large software company.

The problem is, I love working on a variety of tasks throughout the day and solving interesting problems. But in a large marketing department, you have someone for each of those roles. So as much as I tried to innovate and learn, I was stuck doing the same rote things.

Meanwhile, freelancing was becoming more lucrative and exciting—but I wasn’t ready to make the leap.

I didn’t know what it would be like

As much as you can prepare for a career change, you never know exactly what it’ll be like.

I knew that I loved working with smaller businesses and wearing many hats. I’m also rather opinionated and like to do things my way without having to convince an entire department.

But just because I like to do that as a side hustle doesn’t mean I would love doing it all day, right? I was afraid that I’d miss my coworkers too much, or that I’d throw my family into financial ruin.

What it’s really like to be a self-employed consultant

Self-employment is equal parts awesome and exhausting at first. For me, it’s totally worth it. For some, it may not be.

Some of the great things:

• Make your own decisions and stop consulting people for everything.
• If you enjoy the process of building a business and strategizing, then having your own is exciting.
• Every day is different because of the variety of problems you’re solving.
• You get to use new tools and technologies all the time.
• You’re constantly learning and trying new things.
• You meet a lot of new people.
• Your income potential is solely based on your decisions, not based on whether your company is willing to give raises.
• Unlike a lot of entrepreneurs, there’s not much to figure out or pay for up-front. You don’t have to invest thousands to see if your business will work. You’re just finding mini-jobs and building a reputation.
• No one is telling you to show up to things at a certain time. You set your own schedule.
• It’s likely that you will have less meetings than you did at your job. Can I get an amen?

What’s not so great about being self-employed:

• Unless you have people you work with every day and form relationships with, it can get lonely (this can be solved later with subcontractors/employees you hire).
• If you’re billing hourly, you earn $0 for any hour you’re not on the clock. This makes days off and vacations pretty stressful unless you’re making a surplus. To escape this, you need to come up with passive income.
• Self-employment insurance and taxes are the definition of not fun.
• Dealing with accounting and taxes, at least for me, can be incredibly stressful until you understand it.
• As you scale, it can be difficult to find good talent to subcontract to—the best people are building their own teams, very busy, or charge too much for you to make a profit.
• You have to be proactive and make sure there are people in your funnel at all times.

Lesson 1: Start a side hustle before you feel like quitting if you can

I can’t imagine quitting in the middle of a pandemic without the safety net that my existing side hustle provided.

Not only did I have about 1/3 of my income covered when I left, but I also had the confidence to know I could get more clients and fill up my time within a few weeks of leaving.

In fact, I was turning clients away by week 2 of working for myself.

How can you start a side hustle? The easiest way is to make a profile on Upwork and start small. Bid on a couple super easy, temporary, and low-paying projects. We’re talking like 5 hours of work per project. When you’re done with these projects, ask the clients to leave a review and explain that you just started on Upwork and need to build a reputation.

They’ll be so happy with your work (because you were overqualified lol) and they’ll give you the fivest of stars.

How do you make time for a side hustle?

I can’t answer that question for you because everyone’s life is different. I got up at 4am most mornings and worked for several hours before starting my regular job, plus logged in on lunch breaks and many weekends as well.

If you’re not willing to endure discomfort for a period of time so that you can eventually enjoy a comfortable lifestyle, then this may not be for you.

Lesson 2: Self-employment is not for everyone

As much as I love this, it’s just not for everyone.

When people look at me like I’m crazy for getting up early to work, or ask how I can manage so many clients at once, it’s usually a sign that they’re not the type of people to enjoy freelance consulting.

Before I set out on my own, an ex-freelancer I worked with told me, “The worst thing about freelancing was constantly generating new business.” That made me scared until I had tried it myself. I realized that I actually enjoy going out and getting new clients, and I only needed a few hours every month to do so.

There’s absolutely nothing wrong with not liking freelancing. Everyone’s different and that’s cool! It’d be bad if everyone wanted to freelance.

Here’s a quick self-assessment for whether you’ll like self-employment:

• Do you need someone else to tell you what to do, or do you prefer figuring that out on your own?
• Are you calm when a paycheck comes in a few days late?
• Are you good at saving during the highs to ride out the lows?
• Are you able to set effective boundaries around your work and defend those boundaries to people who challenge them?
• Do you enjoy meeting new people and demonstrating your expertise for them?
• Are you able to organize many competing priorities effectively?
• Do you always work on the simplest task ahead of you, or do you tackle the highest priority task first?
• Are you good at having difficult conversations with people and avoiding arguments?

Lesson 3: Charge more

One of the lessons I mercifully learned very quickly is: it’s easier to charge more than you might think.

If you start out with $15-$40/hr work, you are likely to get a lot of penny-pinching clients who don’t have a solid budget.

These clients are usually very stressful to work with. Why? Because they’re stressed out every time you bill them.

I’ve also found that these types of clients have weirdly high expectations, low tolerance of boundaries, and other issues that make them generally unpleasant to work with.

Now, there are plenty of exceptions to the rule and I’ve enjoyed excellent client relationships before at the lower end of the market. But this is an actual thing.

Sometimes all you need to do is raise your rates and you’ll have a completely new experience.

Pro-tip: regardless of what rate your charge, you’ll run into some people that seem to be very nervous about hiring you and what it’ll cost. If you can afford to, look for clients that aren’t worried about your rate or your ability to deliver. It will make your life much easier.

Lesson 4: Always be learning

It’s easy to get in a rut of constantly billing hours and getting new clients. The problem is, you need to learn new skills in order to grow and charge higher rates or do new things.

Set some time aside to learn new skills and hone yourself as a consultant.

If you simply can’t afford the time it takes to learn new skills, you are probably charging too little.

Lesson 5: Tie your services to value

Marketing operations is a fairly broad job description and you’ll get different definitions depending on who you ask.

I personally focus on the tech side of operations. I set up processes, automations, integrations, analytics, and other technical stuff.

But sometimes marketing operations includes deploying emails, giving strategical advise, analyzing data to gain insights, auditing webpages, and other things that can contribute directly to the bottom line.

There are several ways you can bring value to a client:

• Save them time
• Make their customers happier
• Make them look good
• Contribute to their revenue
• Save them money (on people, tools, etc.)
• Give them peace of mind

Don’t underestimate the power of saving a busy client time and giving them peace of mind. High performing and high earning clients value their time and sanity.

Lesson 6: Figure out which clients are dragging you down

Sometimes it’s obvious, sometimes it’s more subtle.

The client that pays the lowest is often holding you back, but that’s not always the case. Maybe they’re the one bringing you the most joy!

Some ways clients can drag you down:

• Extremely inconsistent work where one week you have nothing, and the next you have 20 hours to complete
• Tight deadlines whenever they assign something
• Unreasonable expectations, such as blaming results instead of process
• Lack of trust in your work
• Constant interruptions throughout the day
• Too many zoom calls
• Penny pinching, unwilling to pay to make dreams a reality
• Bad boundaries around your weekend, time off, or emergencies that come up for you
• Asks you to explain why before you do anything (goes back to lack of trust)

If you have a client that checks a few of those boxes, you should really consider moving on from them.

Depending on the problem and the effect it has on you, you can also try saying that you’re raising your rates by 2x or 3x next month. Do this if you’re ok with either outcome: whether they say they can’t afford it and you move on, or if they say they can afford it and you continue working with them.

Lesson 7: Plot and scheme

If you want to continually grow and improve your business, you need to constantly be thinking up the next thing.

It’s easy to go on autopilot delivering tasks for clients and occasionally finding new ones, but you need more than that.

You need to stay a step ahead and spend time working ON your business, not just IN your business.

• Track your time throughout the day (not just with client work) and figure out how long it takes to do things. This will be valuable later on when you want to outsource.
• Look for ways to provide yourself a competitive advantage. Maybe it’s a professional-quality intro video for your site that most consultants wouldn’t invest in. Maybe it’s a piece of software most people don’t have that lets you do more, faster.
• Set goals and work backwards from them. If you have a revenue target, figure out exactly what needs to happen to hit that. Then go out and make those moves.

I hope this has been an informative look at what it’s really like to take the leap into self-employment.

If you’re also a consultant in the marketing operations space, connect with me on LinkedIn!