Ask a Project Manager #6: How Do I Become My Own Boss?


May 27, 2020


Rachel Gertz


Digital PM trainer and Digital Project Management course instructor Rachel Gertz (@thestraymuse) is our resident advice columnist for our Ask a Project Manager series, where we aim to get real, get deep, and get practical with your most burning questions about life and career in the creative industries. In her final column, Rachel takes us through the highs and lows of what it really takes to start your own business.

Dear Rachel,

I’m wondering how you stay motivated and inspired and what would be the first tips or steps you would recommend in becoming your own boss and being able to get residual income.


Be My Own Boss

Hi Be Your Own Boss,

Your question is a sign that you are crossing into the seductive realm of being the captain of your own ship, and you know what? It’s nice over here. I’ve owned my business for eleven years this year, so I can tell you a bit about the bruises and blunders, the fits and starts, and the heart soaring moments of being your own boss. Plus, I can share a smidge about the things that get me fired up and get me out of bed to do it all over again tomorrow.

First things first, when you say “be your own boss,” I interpret this as two paths. One, you want to become a freelancer and earn an income to support yourself where no one employs you. Two, you want to start and run a company that employs others so that you become your own boss and other people’s, too. I’m not sure which path you’re most interested in, but I’ll shine some light on the similarities around both and hopefully this will help you decide what makes sense for you.

To be or not to be (your own boss)

The obvious first question is ‘should you take the plunge and become your own boss?’ People have written miles of words on this topic and start content fist fights over who has what it takes to be an entrepreneur, so I am going to keep this tidy and tell you how I knew I wanted to be one. You have to follow your heart and your gut on this one…but it’s about breaking the rules, letting your hunger eat you up, and being prepared to weather the weather while slurping up the bliss of it all.

Learn the rules and break them

I distinctly remember having very strong feelings about ‘not wanting to follow the rules’ as young as five and I would bristle at any traditional notion of how people got things done. I never wanted to have just one job. Cut to me mashing yogurt, sprinkles, cinnamon and chocolate ice cream in a bowl at 11 pm because I wanted to invent a new dessert. To this day, I refuse to follow a recipe. I’d rather go on gut feel and it drives my husband/ business partner up the wall.

Our business is a manifestation of taking the old (apprenticeship) and remixing it with the new (remote online learning). For you, Be Your Own Boss: do you feel like you like to follow the rules and follow the pack? Or do you get a gut feeling that you could reinvent something or do it in a different way? Or do you straight up hate the idea of someone being your boss? That’s another good indicator this path is for you.

Dream up an idea that gnaws at you

Up until my partner and I decided to convert our design studio into our current apprenticeship for digital project management training, I never had an idea I cared about so deeply it would keep me daydreaming till my eyeballs hurt. For us, training digital PMs is a way to redistribute power in a normally hierarchical system in a very homogenous and painfully Caucasian technology industry. With that power shift comes process change and, ultimately, companies who contribute to an inclusive technology industry because we are all focused on hiring and training non-binary and underrepresented folks into leadership roles. What idea keeps your fingernails clicking and your lips pursed in thought? What fuzzy problem makes your scalp itch and your cheeks tingle? This is the thing that feels impossible or undefined but it keeps circling around your head like a mosquito with a taste for blood.

Did you know? Most businesses fail and that’s okay.

“Data from the [Bureau of Labour Statistics] shows that approximately 20% of new businesses fail during the first two years of being open, 45% during the first five years, and 65% during the first 10 years. Only 25% of new businesses make it to 15 years or more. These statistics haven’t changed much over time, and have been fairly consistent since the 1990s.” —Michael T Deane

If we broke it down to show you and four of your friends in business, this is how it might look after 2 years, 5 years, 10 years, and 15 years.

2 yrs: 1 😭 4 😎

5 yrs: 2 😭 3 😎

10 yrs: 3 😭 2 😎

15 yrs: 4😭 1 😎

But don’t let it get you down. If running a business was easy, everyone would do it and then there would be a million Netflixes. Boring.

Expect the worst

Running my own business is, hands down, the hardest thing I have ever done. To put it in perspective: I felt ashamed at my clinic clerk job when I watched an 87 year-old man pee his pants because I didn’t have training on how to help him to the bathroom in his wheelchair. My cheeks flamed red as I watched my tray flip over dropping my entire table’s dinner to the floor at my first waitressing job. My neck flamed red when a sweaty, sour old tile-setter groped me at my onsite painting job as I attempted to scramble away from him while painting the baseboards. Those were tough moments.

But I tell you, they were nothing compared to relaunching our own company. Until then, I had never, in all my jobs, laid staring up at the ceiling night after night in year one and year two blinking back the splotchy shapes that were tears leaking out of my swollen face, wondering when we would go broke and be kicked out of our apartment on East Hastings because of cashflow challenges. The terror of pausing the locomotive and reversing direction, relaunching our whole business, starting from ground zero with curriculum, marketing, and trying to sell a course that nobody had tried yet meant daily paralysis. The tears and the stress battered us in alternating waves. I got all my grey hairs in my mid-thirties. These depressing and manic moments last so long that you start seeing yourself and your world in patches of grey, and your friendships fail, and you don’t call your mom, and forget what weekends are, and you get holes in all your socks and the loneliness and self defeat crushes your soul—whoah. I’ll stop there. Don’t let me kill your dreams yet. It’s not all bad. It’s not! At least not once you get your business up and running and defy the odds of business failure.

What about you, Be Your Own Boss? Are you excited to have your every insecurity tested day after day inside the the pressure cooker of entrepreneurship? If you’re still nodding, this is a good sign. Keep reading.

Want to find out how NOT to freelance? This article by our Coax writer, Morgan, is the best.

Get drunk on the good stuff

The thing is, as a business owner, you make the rules. And you don’t have a boss telling her you’re letting her down or not working hard enough. So I have to be a nice boss and let myself revel in the moments that are so good, it’s like being daytime drunk surrounded by liquid sunshine and sage. Let me tell you, Be Your Own Boss, these moments are what makes everything—the anguish, the fear, the inconsistency, the long hours, the self hatred—totally worthwhile. I get to beam at my apprentices when they come back with stories of how they have reset relationships with people at work who were super hard on them, or have clawed back a project from the brink of death. When a prospective partner calls, I get to chat confidently about our program because I know it works and that feeling—the feeling of knowing that all you have to do is tell stories about how the companies you help are kicking ass to make them go ‘sign me up!’—THAT makes it worth it.

The experience of running a business lights a torch to your Imposter Syndrome and makes you feel like you could hug yourself because you bled your metaphorical blisters and burned through your own self doubt and came out triumphant on the other side. It is the glow of a thousand suns seeing Stripe payments hit your account and knowing: I worked so hard for this and I earned it.

Have you felt that bliss, Be Your Own Boss? If not yet, it is one of the best feelings you’ll ever feel. Does this pour some fuel on your entrepreneurial torch?

The feeling of turning a spark into fire is something only business owners and Tom Hanks from Cast Away know about intimately.

How to get started

Now that I’ve set the tone, here’s the practical stuff to help you mentally prepare for the journey. If you’re starting to pack your bags, read this part first.

In this precarious gig economy, it seems like virtually everyone will be forced to become their own boss anyway. But if you are going that route, don’t become a freelancer till you’ve worked for someone else for at least three years, if you can help it.

You learn self-discipline, how to be wrong, how to build trust, and how to find your footing as you maneuver the corporate (or not so corporate) ladder. Otherwise, you will make horrible mistakes and they will toss your confidence, or you build up bad habits that make you think your way is the only way to do things and your narrow approach will come back to bite you in the butt. If you can’t land a job working for someone else right off the bat, try working alongside freelancers who have years more experience and can show you the ropes to help you avoid getting rope burn.

If there was one thing I wished I’d done early in my career, it would have been this. It staves off the anxiety of not knowing how to set up your process and feeling like an imposter.

Know if your work is good

If you’ve worked a job for someone else for a while and you want to try things on your own, first make sure that people want to buy your idea or your product. This sounds simplistic, but if nobody likes what you do and it doesn’t stand out in some way, it will very tough for you to be successful when you go solo. So the best way is to get some honest feedback.

Ask your friends, your family (if you really trust them), and trusted allies at work if your work or idea is good and if they’d buy it. Ask ten strangers. If they answer emphatically or too quickly, be critical of that. They should be thoughtful and intentional in their responses. They should offer honest feedback. Consider submitting your work to a group of fellow designers on a portfolio platform like Behance or Dribbble or ask people who don’t have a creative bone in their body and get direct, gristly feedback. See if you can handle the criticism that comes from displaying your soul through your work. You might not like their responses, but you’ll need to practice resilience if you want to freelance.

Know how much money you want to make

Start earning some extra cash on the side by moonlighting. Pick up a client or two by creating a one-page site and asking friends and family first if they know anyone who needs your services. Test your rates by thinking about how much money you want to make during the year and offering your services at market rate (~$50–75/hr to start). If you’ve had three years of practice, you should be able to charge the equivalent of an intermediate salary $60-80K loosely split over twelve months. But don’t forget, when you go solo, you have to cover your own business expenses like healthcare, business taxes, software and equipment, and new business entertaining, so you want to add up your expenses and calculate how much more revenue you need to generate to set aside money for your personal expenses and savings.

You have to ask yourself: Do you want the work to offset your current salary and go full solo, or do you want it to just bump up your current income? As you incorporate, scale your company, and hire employees, you have to modify your pricing approach since now you’ve got mouths who feed you but also need to be fed. The transition to full time freelance (and ultimately company owner) can be fast or it can be slow, but ride it out at the pace that makes sense for you. Do you have an idea of your goal salary, Be Your Own Boss? If not, it’s a great time to start thinking about it.

Know how money, legal stuff, and taxes work

This is super important. Every country has different laws about how much money you need to set aside for taxes, and in many cases, there is a threshold minimum you need to make before declaring that you’ve made it. Do your research. Consider joining a freelancers union and connecting with a great lawyer (unions have great resources) who can help you button up your legal contracts. Yes, you need those, and yes, you want a lawyer to vet them for you. You might also want to consider finding a bookkeeper to help you manage all your receipts and accounts receivable because these can get pretty hairy and you don’t want the IRS chasing you down. Don’t forget to factor these costs into your revenue goals because they add up quickly. Become fluent in talking money, thinking about money, tracking money, and (ironically) letting go of the mind control money has over you. Learn the business of design.

This is an excellent little read by Ryan Rumsey: Business Thinking for Designers

Know what clients and customers expect

Clients are paying you to deliver a valuable good or service. They always want to know the answers to these three questions: “Where are we, where are we going, are we okay?” If you can make sure to keep them in the know at all times about your timeline, your scope, and your budget, you will be miles ahead of many other newly minted freelancers who think freelancing is about living your #bestlife, travel blogging from Thailand, and drinking frothy cappuccinos in handcrafted clay mugs from mid-century modern coffee shops. It’s a lot more sweaty, pajama pants-y, and ramen noodles-like than that (at least at first).

Outline what is in bounds and out of bounds for your scope and explain expected behaviours so clients know when to expect a warning. If we don’t set those expectations up front, it’s so much trickier to wrestle them back later. Aim to work with no more than 3–5 active clients at any given time and about 10–15 over the year, this will mean you can give each the attention and focus they deserve while making sure that no tyrannosaurus of a client will lumber away and take a ghastly chunk of your revenue with it. Psst: We teach these core project management skills in our digital project management courses, if you need a little guidance at the elbow. What do you think, Be Your Own Boss? Are you getting excited yet?

Know it will be a slog

Expect to work on average anywhere from 50-90 hours a week when you first get set up and potentially years into the job. There is a ton of administration work, processes to document, and cold calls to prepare for. Think of your week in morning and afternoon chunks (3 hrs in the am, 3 hrs in the afternoon). This helps you time block and do similar types of tasks at the same time so you don’t exhaust yourself. Find your moments of rest and retreat when you start noticing you’re close to burnout. Consider that many freelancers burn out in a year or two once they run out of contacts and are not sure how to market themselves beyond their networks. You can either push through and establish new contacts and partners who can help refer you out, or you can pack it in and get a job. There is no bad choice, just the choice that makes sense for you.

Know you’re not alone

Despite my candor about how lonely it is being the queen of your own castle (and it is), the one nice thing is that we’ve hit an unprecedented time where half our workforce is or will be precariously employed in the gig economy as freelancers. While this is staggering on so many levels, and we need much better worker protection to support us all, there is also power in numbers, and you are not alone. Join freelance groups, join a collective, connect with other business owners, talk about the hard bits that make you want to cry. This is where your strength and solidarity come from. Some of my biggest allies are in a women business group that meets up once a month to talk about goals and blockers, and month after month, these women raise my spirits and get me thinking about new ideas to try in my business.

(Metaphorically) light yourself on fire each morning

Earlier you asked what keeps me motivated and inspired. Well, I’ll tell ya, Be Your Own Boss: It’s letting myself daydream and light fires for the future. I spend a good quarter of my week dreaming up the shape I want to this business to take in five or ten years. As our world systems come crashing down around us, pandemics reign, our environment falls to shambles, and our food supply is put under stress the likes we’ve never seen, I imagine ways that our apprentices could jump on board large scale international food or resource or clean energy projects and rejig old systems that aren’t working anymore. So things that get me excited are in no particular order:

Systems thinking: Understanding how our world is a series of interlocking systems that all add up to make something greater than the sum of its parts. This Acumen+ course on systems practice is on my backlog as we speak.

Researching trends: Studying things like Garnter’s Hype cycle gives you an idea of where different products and ideas will fare over the coming years. If you look around you and think ‘gee, this is dumb, why do we do it this way?’ chances are, someone is working on this problem—or you should.

Design a counter culture: I don’t think our current business models and philosophies are doing a great job of enabling and representing women, faces of color, and non-binary folks to succeed in business and in life. I think this is because traditional business principles value competitive, hierarchical, paternalistic, and white supremacist ideas. We are exploring other business schools of thought like the Feminine Economy and Worker Directed Enterprises because they are at the heart of intersectionality which we know uplifts everyone.

What about you, Be Your Own Boss? What things get you fired up and excited to embark on your own?

It’s a leap of faith—and understanding physics

There is nothing I can do to sugar coat the arduous journey ahead of you, Be Your Own Boss. Making a commitment to work for yourself is a walk across glass and hot coals and all the ashes of your limiting beliefs kissing your heels as you take one step and then another.

You will retrain your relationships with money, time, and value, you will stretch yourself in ways you thought only bandaids could, and you will have to fight the depression and loneliness of being ‘at the top.’ You will survive bright times and dark times. You will weep (from joy and from sadness), but if you decide that being your own boss is the thing that you need to do, you will discover a strength inside you that burnishes you from the inside out and you will take those steps bravely filled with hope.

Wherever you are on your path, Be Your Own Boss, I salute you. Everyone walks their path and I wish you light feet and a steady step out on your own.

Yours in the biz world,



Here are some handy resources for you if you want to investigate your future as a badass boss.

Small business research

Small business statistics

About the author

Rachel Gertz is Co-founder of and a Dig­i­tal PM Train­er at Loud­er Than Ten. She trains appren­tices in dig­i­tal project man­age­ment so they can work full time while learn­ing to keep their com­pa­nies hap­py, healthy, and ready for the future. Rachel works on rais­ing tides that float all boats to ele­vate the tech­nol­o­gy industry. 

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