Five Ways to Think Like a Boss
By Jena Kroeker
One thing’s for certain — freelancing involves a different way of thinking. A different lifestyle. Different freedoms. And all this is powered by a particular mindset, one that calls us to “think like a boss.”
If you’ve worked in a corporate job or other type of employment, you’ve most likely had a boss. And each boss conjures up different images and feelings. Maybe some were tough. Maybe some were lenient. Hopefully most were kind and respectful.
Let’s back up and examine what we’re talking about here. It’s commonly known as the “entrepreneurial mindset.” In an article titled “Entrepreneurial Mindset: 20 Ways To Think Like An Entrepreneur,” Thomas J Law defines it this way:
“An entrepreneurial mindset is a set of beliefs, thought processes, and ways of viewing the world that drives entrepreneurial behavior. Typically, entrepreneurs firmly believe it’s possible to improve their life situation and live life on their own terms. They also believe in their ability to learn, grow, adapt, and succeed.”
My first client introduced me to this way of thinking during our initial discovery call over 20 years ago. I’ll never forget what he told me:
• “You don’t work for me; you work with me.”
• “As long as you meet your deadlines, you can work wherever and whenever you want. One day technology will advance to the point where you can work on the beach.”
These statements line up with the freelance rights outlined by Lindsay Van Thoen in her Freelancers Union article, “Do you know your freelance rights?” Specifically, she notes, “You have the right to work where you want,” and “You have the right to work when you want,” among other important rights.
When I first heard that I could do this, I thought, “Wow!” It sounded wonderful. But if you’re like me, it might take a while to transform your thinking after working as an employee. It’s easy to miss out on a few freedoms at first if you’re used to letting others be the boss and define important aspects of your work for you.
Five Ways to Think Like a Boss
So, without further ado, let’s examine some common scenarios and how we can improve them by adjusting our thinking to an entrepreneurial mindset.
1. Design Your Own Schedule.
In your previous employment, you worked in an office from [9:00] to [5:00]. So, it seems natural to say yes when your freelance clients request that you be available between those hours in case they have work for you to do. You get up in the morning, get dressed in your formal work attire, and log in to the computer. As you check your emails and project management software, you see that no work requests have arrived.
Time passes. You organize your paper clips. You play a round of Wordle. You water the plants. You keep the whole eight hours free, just in case. Then, at [4:30], an email rolls in with a rush project. You jump to attention and start working, missing dinner because the project takes longer than you expected. At the end of the day, you’re exhausted, and you feel like you missed a chance to accomplish other things as you sat around waiting.
In a Freelance University Podclass episode, “7 Steps to Adopting an Entrepreneur’s Mindset,” FreeU co-founder Craig Cannings discusses the difference between an employee and an entrepreneur. As an entrepreneur, you’re the one who determines when you work during the week, not your client. It’s up to you to decide when your work hours are and when you book time off. This is important to remember because letting your clients own your schedule turns you into an employee.
In addition to owning your schedule, it’s important to carefully design it by blocking out priority tasks for your business. Don’t just wait for work to roll in. Designate blocks of time devoted to learning, marketing, vision planning, and administration. That way, you’re thinking like a boss and accomplishing more each week. And, in case you missed it, formal attire is not required, unless you want to wear it.
2. Be Decisive.
You’re stuck. You wish someone would make a tough decision for you. This happens often, and it makes you break into a cold sweat:
• Do you continue working with a certain client?
• Do you raise your rates?
• Do you upgrade your aging computer?
• Do you start using that new financial management software that looks promising?
Questions abound, and they require you to think like a boss and make the decisions. You wish you could pass the blame onto others so you aren’t responsible for any wrong choices. You procrastinate and take a “wait and see” approach. Maybe the decision will make itself in time?
Simply put, you must be decisive. In an article titled “The 7 Key Qualities That Define the Entrepreneur Mindset,” Jay Fuchs says,
“Entrepreneurs own all their decisions – good and bad.”
It feels scary. It takes some getting used to. But it’s ultimately freeing. It’s what allows you to take charge of your business and pursue the goals and values that are important to you. You aren’t at the mercy of others’ decisions. Although it’s important to seek advice from trusted colleagues, mentors, business coaches, or a mastermind group, ultimately the decision is yours.
Furthermore, as Dave Nevogt emphasizes in his article “How to Develop an Entrepreneurial Mindset,” it’s important to make decisions quickly. He says, “If you hesitate for too long, you risk missing an opportunity.” Indeed, as the article above states,
“Successful entrepreneurs decide and then get back to work. They know that ‘you can always edit a bad page. You can’t edit a blank page,’ as the author Jodi Picoult said.”
3. Embrace Continuous Learning.
Why didn’t your client tell you that software was becoming obsolete? Now you aren’t able to perform this week’s tasks unless you quickly master a new tool. You sit at your desk, frustrated and crestfallen. Everything was going so well. You knew the software was getting a bit old and glitchy, but so far, it had worked well. You didn’t feel there was any need to upgrade or switch tools.
Now you’re in a difficult situation, with deadlines looming and projects piling up. Until you learn the new software, you’re going to have to ask for extensions. And while you’re at it, did you happen to hear someone say that your rates were $10 lower than other freelancers are charging? When did that happen? Somehow you missed the memo. Oh, wait — there was no memo to miss because you’re the boss!
As Craig Cannings states in FreeU’s “Partner in Your Client’s Success” course, “Never stop learning.” To achieve the best results for your client, he recommends learning as much as you can. Don’t leave it up to your clients to tell you what you need to learn. To think like a boss, be self-motivated and proactive, seeking learning opportunities and blocking out time to pursue them. In fact, look at each situation as a possible learning opportunity, especially when faced with challenges.
And in addition to online courses, workshops, and tutorials, become an avid reader. In an article titled “5 Ways to Cultivate an Entrepreneurial Mindset,” Kim Perell gives the following advice:
“Make personal development a part of your lifestyle. Each day, set aside time to read blogs, articles, and books that help you increase your knowledge, sharpen your skills, and feel even more motivated and inspired to move forward.”
4. Lead and Collaborate with Your Clients.
Your client sends you a project description, but something doesn’t feel right. You’re not sure he’s going to get the best results with the current strategy. And you have a nagging suspicion that your skills have advanced to the point where you could provide greater value by offering an alternate solution. However, the thought of initiating that conversation is terrifying. Who do you think you are, second-guessing a client’s judgment?
So, you decide to follow his specifications to the letter. After all, it’s your job to complete the task, not offer advice. Right? But that uneasy feeling won’t go away…
Remember those words my first client said to me? “You don’t work for me; you work with me.” And working with a client means collaborating to achieve the best results possible. In the “Partner in your Client’s Success” course, Craig Cannings recommends challenging the status quo and never being afraid to share ideas on how something could be done better. When approached respectfully, the worst that could happen is your client could say no.
In my work as a freelancer, I tend to be quite bold about suggesting ideas. My clients may not always think of me as bold because I strive to be polite and empathetic. But when I have a creative idea or new insight that could enhance a project, I eagerly present it to my clients and give them the choice to accept or reject it.
So, along with your ideas and creativity, Craig recommends leading clients with your expertise, initiative, attitude, and effective onboarding. As you think like a boss, you’ll realize ways you can provide respectful leadership that will ultimately impress and benefit your clients.
5. Protect Your Lifestyle.
How did this happen? Here you are, minutes away from leaving for your child’s spring concert, but you’re awaiting a text from your client. She said she had a rush project for you to complete, and she’d confirm by this afternoon. The trouble is, it’s now evening. You have one shoe on and one shoe off, debating whether to shut your phone off and leave … or stay here and wait.
And while you’re waiting, your mind wanders to another concern you have. You made a hair appointment for tomorrow, but if you aren’t able to finish the rush project tonight, you might have to cancel the appointment and work all day. Thankfully, you should know by the morning because your client typically texts you around 5:00 a.m. It usually wakes you up, but that’s just part of the job … right?
One of the surest ways to think like a boss is to live life on your own terms. And one of the surest ways to lose that mindset is to let work interfere with your desired lifestyle. This problem often results from a series of small choices that snowball into a complicated situation that’s tough to get out of.
Maybe you gave clients your cell number, never dreaming they’d use it. Or maybe you canceled your plans to complete a rush project that didn’t end up needing a rush. Once you’ve set a precedent that clients can dictate your schedule, it’s harder to take back control.
It’s not impossible, however, so whether you are just starting out or are in a tricky situation right now, start setting clear boundaries. For example, arrange a meeting with existing clients to revisit your role and define expectations for your work schedule and turnaround times on emails and messages. Then, as you onboard new clients, be sure to communicate boundaries clearly right from the start, preferably in a “Welcome Package” or “Client Standards Policy” where you outline your policies on communication and rush projects.
Above all, as Craig Cannings says in the FreeU Podclass episode mentioned above, “We want to serve our clients well and give them our best, but not at the detriment of the lifestyle we’ve sought to carve out for ourselves.”
Thinking like a boss will allow you to keep carving out that lifestyle. And as you do, you’ll find your voice and confidence grow within this entrepreneurial way of thinking. So, be patient with yourself and keep persevering. In the words of Steve Jobs,
“I’m convinced that about half of what separates the successful entrepreneurs from the non-successful ones is pure perseverance.”
And now we’d love to hear from you! How do you encourage yourself to think like a boss? Please share your thoughts in the comments below.