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Six Ways To Start Thinking Like a Boss

Traditional employment conditions us to be dependent.

When you work for other people, they take care of you. Your paycheck goes into your account and has already been taxed, your 401K has increased, and your company has even covered life insurance. That nice HR person reminds you of the deadline for open enrollment. The corporate attorney handles that cease and desist order. Your manager sets your goals and “develops” you to reach them.   

They also control what you do, how you do it, and what you’re worth. You must be at a certain place at a certain time. Even if you don’t, you still need to put in a certain number of hours or complete a certain number of deliverables to get your paycheck. And your paycheck gives you what they decide is “fair” compensation for your contributions to the overall product or service.

This learned dependence often means that when people start working for themselves, they don’t fully know how to use their newfound freedom or manage the myriad responsibilities associated with running a business. It is a fundamental mindset shift to start taking care of yourself AND break free of the social conditioning that dictates the connections between time and money, “hard work” and “rest.” You have to learn how to be a boss in a world where the vast majority of workers never work for themselves*.

Solopreneurs, in particular, get stuck in an employee mindset because they often don’t consider themselves “real businesses” just because they’re a one-person show. This leads to undervaluing their work and time, which traps them in the same cycle of overwork and underpay that they had when they worked for other people.

You don’t get to fully reap the rewards of independent work if you can’t break the employee mindset. Here are the key mindset shifts that need to happen to claim your freedom like a boss. 

You Make the Decisions and Solve the Problems

When you work for yourself, you are the only person in charge of the decisions that drive your business and therefore your life. You are also the person that has to solve the problems. This means you will need to be (or get) good at more than what you’re an expert in now. You are a great — fill in the blank — graphic designer, coder, writer, etc. The world needs you and your unique skill set. But unless you are also a marketing expert, project manager, business strategist, website designer, HR expert, accountant, and lawyer— all at the same time — then you’re going to have to learn some new things and wear some other hats.

Now, I’m a big believer in delegating/hiring experts when that makes sense, but chances are you won’t have the funds to always do that. And even when you do have the funds to do that, it’s up to you to decide what you need, find the right person, and integrate them into your business. Be ready to roll up your sleeves and learn new things constantly in order to keep the lights on and the doors open.

You Hold the Purse Strings and Fill the Purse

When you’re 100% in charge of the money that facilitates your life and the time it takes to make it, you think about it in different ways. When you work for someone else, you might not even know what they’re actually charging for the end product and how your time fits into it. As a business owner, you need to charge enough to cover not only your time but also your overhead, taxes, benefits, PTO, and everything else it takes to run a business. One of the biggest mistakes new freelancers make is charging a similar rate compared to what they were making when they worked for someone else. You are a business now, not an employee - what you got paid as an individual contributor is not going to cut it.

This is a big one for solopreneurs. You might have much lower overhead than a larger company and so you justify hourly rates that don’t include the costs it takes to run your business of one. A business of one is still a business – your clients need to be paying you like a business.  

You Know What You’re Worth and How To Ask for It

This applies to everyone, not just business owners. Our society has created a stigma around talking openly about money and compensation and ultimately, what that does is reinforce power structures where people get paid less than they deserve. When you work for other people, you have the luxury (or crutch) of only having compensation conversations with your boss. When you work for yourself you need to be very clear about what you’re worth and get comfortable talking about money with other people (clients, staff, other freelancers) regularly.

You Decide What You Do and When You Do It

In exchange for the added responsibility, you get flexibility and control over your work and life. This can take some getting used to when you’re accustomed to other people telling you what to do. This flexibility means that you have to think carefully about what you prioritize. Many new (and not-so-new) freelancers get stuck doing the same things they did when they worked for someone else, even the things they hate. When you’re the boss you have to think intentionally about your time, revenue, and business model to make sure you’re doing what you love. That’s right – LOVE – because if you’re going to hate your work, you might as well and go back and do it for someone else.

You Develop Yourself

In order to be successful and get those top rates, you need to be great at what you do. You also need to be able to pivot quickly and learn new things on the fly. You have to have a process for setting your own goals and making them happen. You are the only person in charge of “developing” yourself and your business into version 2.0. When you work for other people, they perpetuate the myth that only an outside perspective can show you what needs to change. While an outside perspective can be helpful, ultimately you know when something isn’t working and have the power to change it, whether that means taking a course, investing in a coach, or getting a new certification. The pay-off is so much better when you’ve decided what needs to shift and take the necessary steps to do it. 

You Decide When To Not Work

We’ve been taught that work = virtue/worth/value and idleness = laziness/indolence/inadequacy.

When people start working for themselves, they often can’t think outside the box of the 40-hour workweek and eight-hour workday. You still feel guilty when you have a day (or hour) with nothing to do even if financially, you’re fine. This can lead to people trying to fill their days with work, even when they don’t need the money or pricing their work so that they must work constantly to make ends meet.

When you’re the boss you get to change the relationship between time and money, you get to decide how many hours you work in a day, week, or month. Want to work a 20 hour week and still make the same money? Do the math and price your contracts accordingly. Of course, that all has to be backed up by knowing what you’re worth and building your business model around your life, not just your bank account. Sometimes we chase a full workload because it validates us, not because that amount of money will actually change anything in our lives. When you work for yourself you get to choose rest and not feel guilty about it.

On the flip side, you can also choose to work your ass off for a period of time in order to take an extended vacation or retire early. That’s the beauty – you get to choose and, in the end, the results are yours. Those days you spent working your ass off went directly into your bank account, your retirement fund, your business, not someone else’s.

 Working for myself is one of the greatest gifts of my life. It saved me on so many levels and has given me a pathway to a fulfilling life that I would not have been able to find otherwise. But the truth is, it isn’t for everyone. Having complete control over your time, work, and life sounds amazing until you realize the level of responsibility that gives you. Working for yourself is not the easy route to money but it’s the best route to freedom if you’re willing to work for it.



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