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Becoming CEO: Your Questions, Answered

becoming CEO- Jessica Lawlor

The countdown is on! In less than two weeks, I will officially become my own boss (Missed the big announcement? Catch up here!) On February 1, 2016, this new journey officially begins.

Your support has been nothing short of incredible- I’m so grateful for this community! Thank you.

As promised, I’m bringing you along for the ride- giving you a glimpse behind-the-scenes of the exact steps I’m taking to make this work. You can check out my two weeks out update here.

In addition, I invited you to ask me anything about this decision, my plans and how I’m going to make this work. You asked some great questions that I’ve answered below.

I’m telling all! Here are the answers to your most pressing questions about me quitting my job to become my own boss.

Preparing to Make The Move to Entrepreneurship

How did you decide that now is the right time to quit your job to take your business full time? The truth is, there’s never a good time to make a big, bold move, especially when that decision impacts every single area of your life.

I spent years preparing to make this decision, but I would say October is when I really decided that I was going to quit before the end of 2015. After that, it was really challenging to find the right time to actually say the words out loud. When you have no other job to go to or someone setting a deadline for you, it’s really hard to know when the time is right.

Finally, in mid-December, I decided that there was no time like the present. What was I waiting for? Every day I put off making the decision, I started to feel worse and worse. Finally, one Monday in December, I said to myself, “This is the week. Wednesday is the day.” And I woke up on Wednesday, went into work and did it.

Are there any preparations for this you wish you had started sooner? I’m proud to say, I can honestly answer this question with a NO. In fact, I put off actually quitting my job for several months because I wanted to keep preparing. At some point though, you need to make the leap, and honestly, as I said above, there’s no “good” time to do that.

My preparations for quitting my job included: developing a strong personal brand through my blog/social media (this has been several years in the making), developing a side hustle and starting to bring in extra money on the side of my job (I’ve done this for the past three years), taking a hard look at my finances (I created my finance spreadsheet in October), researching healthcare (November/December) and finally putting in my notice (December).

For someone looking to make a similar move, I recommend starting the process NOW. Go to work every day and be the best employee you can be, but also look out for yourself and start building your brand and doing as much freelance work as you possibly can on the side.

What’s the reaction been from your family and friends? Mostly, pure excitement!

My parents were skeptical at first (mostly because, hello, they’re my parents), but they’ve definitely come around and are excited for me. Their biggest concern was finding health insurance, so since I’ve overcome that hurdle, they are satisfied. My dad always tells me how proud he is of me and my “hustle” so I know I have their support and that they believe in me.

My friends have been amazing. My two best friends are my biggest cheerleaders- in fact, my one friend quit her job last year to become a full-time yoga teacher, so she’s been a great resource and sounding board as I move through this process.

I was blown away by the support of my entire community and network when I spread the news. The number of likes on my Facebook post, tweets, Instagram comments, emails, phone calls, text messages and traffic to the blog post- truly, I was blown away. It was extremely hard to get anything done the day I made the announcement because I was so distracted by the wonderful people in my life.

Even my current bosses and colleagues are happy for me- both told me when I gave my notice that they always knew if I left the company, it would be to start my own thing.

I will say, in sharing the news, I received negative comments from maybe two people, total. I believe that their negativity is more a reflection of them and their own lives and not me and my goals, so I’ve chosen to ignore their negativity and focus on the immense amount of positive support I’ve received.

The Practical Stuff

How are you going to live? How will you pay rent, car loan, healthcare, etc.? Quitting my full-time job to make this move to entrepreneurship wasn’t a decision I made lightly. I’ve been preparing for this moment for years, both mentally…and financially. For the past three years, I’ve been steadily working on my side hustle- all of the money I earned from my freelance work was put into a separate bank account that I have never touched. I’ve saved almost a year’s salary from my freelance work, so I feel comfortable financially, knowing that I have savings to fall back on, in the case of an emergency.

Similarly, before quitting my job, I spent a ton of time studying my finances. My friend Julia helped me create a budget spreadsheet, outlining all of my current expenses, as well as my income. I was able to take a hard look at what I spend each month (student loans, car payment, EZ-Pass! All those things quickly add up!) and I was able to see exactly how much I’d need to earn in order to be able to maintain my current lifestyle.

In addition, I’ve chosen to live at home in order to save money, rather than spending that money on rent or a mortgage. It’s a decision I’m proud to have made. I love my family and am grateful to my parents for giving me a home, but no doubt, this is a sacrifice I’ve made in order to be able to chase this dream of mine. Once I feel steady and comfortable in my new role (hopefully in the next six months to a year), I plan to move.

Will you have health insurance? Yes! Thanks to the Affordable Healthcare Act, figuring out health insurance isn’t as challenging as I’ve heard it once was for entrepreneurs and small businesses. The process of applying actually wasn’t as bad as I had anticipated. It took about an hour to answer all of the questions (the hardest question is estimating your income for the year ahead!) and then you’re presented with several different plans to evaluate. I spent time browsing through about nine different plans in my selected category, checking to make sure my current doctors accepted that type of insurance and finally, choosing a plan. My current health insurance ends on the 31st of this month and my new insurance kicks in on February 1!

Because the price you pay for your insurance is based on your estimated income, I plan to keep a close eye on my income throughout the year. If I make more (or less) than I anticipated, I can change my plan or pay the difference at tax time.

Are you getting your own office? Do you plan on working from home or setting up shop somewhere? I’m not quite sure yet! I plan to do some renovations to my bedroom to set up a home office area, which I’m really excited about. I currently spend most of my time working from my kitchen table and that has worked out well for me, so far. I truly can work from anywhere, as long as I have my laptop!

I’m also not 100 percent sure of what my daily schedule will look like yet, so it’s difficult to say where I’ll be working from, but that’s the beauty of this whole working for myself thing. I do know that I love to interact with others and get out and about, so I anticipate many in-person client meetings, coworking, as well as scoping out various cafes to set up shop in. Any suggestions for places in the Greater Philadelphia area I should check out?

Achieving Work/Life Balance

When will you have personal time? When will you have time off, a vacation, sick day? These are all questions I’ll figure out with time, but thinking about it now, I’ll be working completely for myself, so I get to make these decisions. If I wake up on a Wednesday and don’t feel well, I can choose to stay in bed all day and do double the amount of work on Thursday to make up for it.

Similarly, I do plan to take vacations. Being my own boss gives me the freedom to travel even more, since I can work from anywhere. I plan to spend a few weeks this summer working from Ocean City, NJ, where we’ve rented a condo for a month, my sister and I are planning a trip to Europe in the fall and I’m hoping to do a yoga retreat in Costa Rica next December. Travel is super important to me, and I’m excited to continue making that a priority.

What kind of schedule will you try to start and how will you attempt to achieve the elusive “balance”?

I’m sure developing a schedule and routine will take a lot of time, especially as I’m ramping up, but here’s how I’m envisioning my days, at least for right now.

I’m an early bird. I get my best and most creative work done early in the morning. Even though I don’t have to commute or have anywhere to be early in the morning, I still plan to continue my 4:45 a.m. wakeup time (at least, most days). I always start my day with a workout (I’m obsessed with Focus T25!), so I’ll do that each morning, shower and then get ready as if I’m going to work…except instead of putting on tights, a dress and heels, I’ll change back into my PJs! 🙂 I’ll head downstairs and set up shop at the kitchen table where I’ll get to work at around 6 a.m. I envision myself spending several hours in the morning doing client work and working on this blog and my personal projects.

Since my creativity seems to wane as the day goes on, I’ll plan to schedule calls and meetings in the afternoon, since that usually perks me back up. I’ll also plan to dive into my email inbox a little later in the day, as well.

Some days, I’ll work from home. Others, I may work from a coffee shop. Some days I may go to a 9:30 a.m. yoga class and other days I may take an afternoon power nap and pick work back up in the evening. When the weather gets nice, I look forward to mid-day runs outside. The possibilities feel endless!

In terms of finding balance, again, I’m sure this will be a struggle and something I’ll need to constantly check in with myself on. In the beginning, I’m sure I will take on too much work and struggle to find down time. Over time, I’ll begin to find my groove and the appropriate amount of work that sustains my life, but also gives me a little more freedom. I’ll be sure to check in and update you on how this goes!

How will you stay motivated? I am a pretty motivated person, in general, especially when it comes to projects and work that I’m passionate about. Since I’m handpicking my clients, I’m anticipating that I’ll find motivation because I’ll be doing work that I love. However, I’m also realistic. Even if I love a client, that doesn’t mean I’m going to love every part of their business.

I’m motivated by deadlines, so I plan to set lots of those for myself. I’m also motivated by connecting with others, so I plan to continue scheduling lots of calls and meetings to grow my network and collaborate with like-minded people.

Finding Work/Clients

What exactly are you going to be doing to make money? An excellent question! I outline my services in detail in this post and here on my services page, but essentially I’m going to be combining all of my passions and skills into a career with multiple different income streams.

  • Content development/writing
  • Communications/PR consulting
  • Social media
  • Blog management
  • Personal Branding Bootcamp sessions/consulting
  • Teaching yoga
  • Public speaking
  • Blog/courses/products

Will you share this news with your current clients?

Yes! I actually let my current clients know my plan long before I even gave my notice. In fact, a couple of my current clients have served as awesome mentors and shared their advice and wisdom with me as I moved forward with this decision. Similarly, a couple of my current clients are thrilled about my news because now we have the opportunity to do even more work together. I love my current clients and am so grateful to have the chance to work with them.

Do you have a new strategy in the works to get additional clients?

Great question. I’m going to have to get comfortable with selling myself, huh?

Right now, most of my prospective clients have come from referrals from current clients, as well as spreading the news on my blog/social media networks. After I shared my announcement, I received several inquiries from folks who have been following my journey or read my blog post and thought there might be a fit for working together.

After this initial wave, I’ll have to check in and see where I’m at with my volume of work. I anticipate I’ll have to get comfortable with proactively reaching out to prospective clients, but for now, I’m going to continue responding to requests and leaning on my awesome network.

How do you find your freelance writing gigs? Are you subscribed to a particular web service?

My freelance writing gigs have mostly all come from developing a strong personal brand! All of my current major clients have found me through this very blog or through social media.

I also spent years writing for free (and still do in cases where I feel that piece of work may elevate my brand) to build my portfolio. I am not subscribed to any web services or job boards, as I find they often only promote lower-paying, low-quality writing assignments.

There are also so many valuable resources/communities online you can join to gain further support. The Write Life and Be A Freelance Blogger are two of my favorites- TWL has several posts outlining blogs/websites that pay for writing.

Getting Real

Are you anticipating finding out that you had any misconceptions about the reality (the not-so-glamorous parts) of working for yourself? Totally. Every day, I remind myself to take off my rose-colored glasses. Yes, there is SO much to look forward to, but I also know there are many challenges ahead.

One of my greatest fears around this whole journey is: will I even like this? Will this turn out the way I hope it will? Will I want to go back to a 9-5? The answers to those questions will come with time.

But for now, I’m doing what I need to do. I’m doing what I’ve always dreamed of doing. I took a leap. I’m going to make it happen and I’m ready to face whatever challenges come my way.

Do you have a Plan B or some sort of backup financial plan… or are you just diving in 120% to absolutely make this work?

As I mentioned above, I do have about a year’s salary saved, so financially, yes I have a backup plan.

However, no, there is no Plan B. I love the quote “Have no plan B and Plan A somehow works out.” I am going to make this work.

How You Can Continue to Follow Along

Want to stay up-to-date on this journey?

  • Follow me on Snapchat (Username: jessicalawlor). I’ll be giving you a behind-the-scenes look at my first week of self-employment, starting on February 1.
  • Follow along on Twitter.
  • Subscribe to my newsletter.

Have additional questions? I’d love to answer them! Leave them in the comments below!

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Meet Jessica

I live by the saying “Life begins at the end of your comfort zone” and help others do the same to reach their biggest, brightest goals. Read my story here.

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