Asking Not Asking #21: To Keep Going or Not
TINA ESSMAKER / Creative Coach
Dear Tina,
For the past year I’ve been working on building my freelance business. I do copywriting, editing, social media management, and strategy, mostly for individuals and small businesses. I’ve also worked with a couple of startups. Before this, I was on contract with a company for 12 months and even though I wasn’t full-time with them, it felt like a full-time job.
I decided to give freelance a go after the contract ended and I assumed work would just come in. But the truth is, it hasn’t. Every month I tell myself this is it. If I don’t get more work, I’ll start applying to companies and take a break from freelancing. But I don’t want to do that. I want to keep working for myself and really build something I love.
But it’s so hard. I don’t know why I thought it would be easy. I guess I was naive about what it takes to build a business. Now I’m wondering how to move forward. Should I give it another year? How long can I expect it to take to build my business and how can I get a steady stream of work coming in? I’m not the best at marketing myself, even though I help clients figure out their messaging. It’s different when it’s me.
I guess I’d like to know if I should keep going or call it quits. And if I keep going, what’s next?
Thanks for your help!
Gratefully,
To Keep Going or Not
Dear To Keep Going or Not,
Many years ago when I was mulling over what I thought would be a momentous decision, a mentor told me, “You can do anything for a year.” It’s true. A year passes by quickly, even if it seems slow in the moment. If you want to build the infrastructure for a successful business, it’s going to take more than a year. The good news is you’ve already put a year in. Now you have to decide if you want to continue building (and it sounds like you do) or if you want to abandon what you’ve built and seek out an opportunity to work for someone else again.
I get it. It’s understandable to feel disappointed after a year of hard work. You’re eager for the return on your investment and you want a payoff, or payout. But the truth is that it takes an average of three years (per my internet research) for businesses to be profitable. You’re a third of the way there. So, do you keep going or not? Only you can decide that, but I can give you a few items to consider before you choose.
I imagine you feel far away from what you want, as David Whyte puts it in his book, The Three Marriages:
“There is no possibility of pursuing a work without coming to terms with all the ways it is impossible to do it. Feeling far away from what we want tells us one of two things about our work: that we are at the beginning or that we have forgotten where we are going...
It may in fact be that the very essence of what individuals have to offer the world is through a close understanding of their weaknesses and blind spots—blind spots in themselves or others. The very dynamic we confront when we feel it is impossible is the very dynamic we will put into the work, a dynamic that will make it distinctive and entirely our own.”
“It’s understandable to feel disappointed after a year of hard work. You’re eager for the return on your investment and you want a payoff or payout. But the truth is that it takes an average of three years for businesses to be profitable.”
Perhaps it feels impossible to get closer to what you want, but I’m telling you it’s not. As David so insightfully notes, you’re likely either at the beginning or you’ve forgotten where you’re going. It sounds like you’re at the beginning, but it wouldn’t hurt to clarify where you’re going and why you want to go there. Knowing where and why will help you move forward even when you feel discouraged as you do now.
Because you mentioned that you really do want to continue building your business, I’m going to go in that direction here. I want to offer practical advice to give you a place to start as you plan your next steps. Here are several actions you can take beginning now:
1. Decide how to pay the bills while you build your business.
Your business needs time to grow and become profitable and that means not prematurely putting pressure on it to be your sole source of income. How much money do you need to make each month? Are there ways you can lower your overhead? Don’t deprive yourself, but be clear about what you need and don’t need. And then know your number—what you need to make each month to cover your cost of living. What can you do now to bring in income to take pressure off of your growing business? What are people willing to pay you for today? Start there.
2. Ask for help from trusted friends and colleagues.
All of us have blind spots. Is there something you’re missing about your situation? With the goal of seeking awareness, I would encourage you to reach out to 3 people who’ve known you in a professional capacity for at least 6 months. Think of questions you can ask them that could give you insight. I did this myself recently when I asked a friend if they would take 30 minutes to answer questions about how they view my business and messaging. My friend’s feedback was brilliant and helped me identify a key piece of my business I had been overlooking.
3. Define the purpose of your work for this season.
When I work with coaching clients, they often want to focus on large swaths of time. I encourage them to focus in on the present season of their work. Sure, it’s helpful to imagine into the future and even set goals for where you want to be in the next 5 to 10 years. However, you can’t get to the future without planning for the present. And when you try to plan for too large of a time period, you get overwhelmed. What do you want to get from your work now?
4. Set achievable goals and work toward them.
Take a realistic look at where your business is now. What are you making, who are your clients, what type of work are you doing? Ultimately, what does success look like for you? If you haven’t thought about it, I’d encourage you to freewrite for at least 10 minutes and put pen to paper to define what your business would look like if it were thriving. That is the dream. Now, look at where you are today. What do you need to do to get closer to the dream? What can you do on a day-to-day basis to get closer to what you want? It can be helpful to set goals in increments of 5 years, 1 year, and quarterly.
5. Paint a picture of what it looks like if you keep going.
Not literally. But think about the details of what your business and life could look like if you keep going. Set aside 30 minutes and write about your ideal day, the clients you’d want to work with, how you would feel, envision the space where you’d work, imagine how much money you would make and what you would do with that money. It could be yours.
It takes audacity to believe we can have the lives we want. It takes tenacity to create something from nothing. But you are not the first and you won’t be the last. It may not happen exactly as you hope. It may be hard and challenging at times. In moments, you may be full of doubt and fear and wonder if it’s all worth it. And you’re not the only one. Many have come before you and many will follow. But this path is yours.
“It takes audacity to believe we can have the lives we want. It takes tenacity to create something from nothing. But you are not the first and you won’t be the last.”
To go back to David’s words, “The very dynamic we confront when we feel it is impossible is the very dynamic we will put into the work, a dynamic that will make it distinctive and entirely our own.” The world doesn’t wait for us. All of us move forward day after day, step by step. Now, you have to choose to move forward in a way that is distinctively and entirely yours. And I believe you can.
To continuing on the path or creating a new one,
Coach Tina
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Asking Not Asking is a bi-monthly column written by Tina Essmaker, a New York City-based coach, speaker, and writer who helps others live into their possibility. To be considered for the column, send and email to tina@workingnotworking.com with a short note about where you're at and where you want to be, and make sure to include the following:
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