I tried freelancing. It didn’t work out. Now I’m going back to an office job.

An honest reflection on entrepreneurialism, employment, and pride.

I don’t think everyone is cut out to be their own boss.

It’s been over a year since I’ve had a regular job with an employer. My last place of employment was a temp position with government working in the economic development department as a career coach for city residents looking for jobs. I thoroughly enjoyed the work, but due to circumstances that came up with my spouse’s job, coupled with knowing my position was ending soon, I left that position and started New Ropes.

Part of what inspired New Ropes was the expanse of different jobs and bosses I’ve had, as well as my experience helping people find work. I was good at it and wanted to continue helping people as best I could. I’ve gone about this through writing, working with individuals on navigating the job landscape, and consulting for a small business with workforce development initiatives.

I thought I could make it work. I thought if my writing took off and if I got more clients then I could provide a supplemental income while we lived off of my husband’s income in the meantime.

I knew it would be hard, but I didn’t anticipate the challenges I would face. Now, my “meantime” has dried up and I’m returning to the workforce.

The dream we’re sold.

Online, we’re constantly inundated with success stories of entrepreneurs who make it big. Everyone talks about how they took the risk and gave their dreams a chance. Giving it their all, struggling through the challenges, and coming out on the other side.

You set up a system for success, track your habits, make your pitches, put in the hours, and find success.

Be your own boss!

This sounded great to me! I was tired of working for others and wanted to try it out. I thought anyone could be an entrepreneur. Now I know I was wrong.

How to make it big.

Honestly, I can’t tell you how to make it in your own business venture. What I can tell you is what I encountered and why it didn’t work for me.

1. I struggled charging people for my services.

My heart is to help people, which is much easier when someone else is paying you. When approached by people for help, I was constantly giving out free advice. How was I supposed to ask someone for money when their unemployment was about to run out? I had a few clients who I charged, mainly those with jobs looking for a new one, but over all I found this challenging. I didn’t even want to turn on paid subscription and limit the resources I could offer someone.

2. I hate pitching myself.

Some people thrive in sales. I am not one of them. I was always worried about talking myself up, over promising what I could offer, and knowing how to measure my value. At the end of the day, I can’t guarantee anyone a job, because I can’t control other people. I can help you with your resume, offer ideas on how to approach the job search, show you where to look, explain what different industries look like, what the trends are, and everything in between. But I can’t hold an employer at gun point and tell them to hire my clients. It doesn’t work like that. Luckily.

Even though my first post was on how to not sell yourself short, I found myself… selling myself short. Something a friend of mine pointed out recently. Quite a humbling experience. And she was right, I was selling myself short and couldn’t find a way to overcome my own inhibitions.

The question I dreaded most was, “so what are you doing now?” I couldn’t hide behind any of the fancy titles I’d proudly held in the past, so I would stumble through my half-assed pitch on how I’m doing my own thing now, writing about workforce developments on a platform called Substack (“What’s that?”), while the listener would nod and maybe ask a few questions until I changed the subject. I got so tired. I felt ashamed for “not working” (not making money) while my husband worked 60-80 hour weeks to support us while growing in his career.

3. I couldn’t in good conscience pay for exposure.

In order to get your writing out there, you need to pay for exposure. Of course, some people go viral and attract all sorts of business, but I don’t think that’s most people’s experience. What most people have to end up doing to get attention is pay for help. You hire someone with connections, work with a coach, pay a publisher, etc. You have to spend money to make money.

I was approached by a firm that publishes work for writers, but at a cost. Instead of being paid for writing, you work with them on a piece, and if they can get it published, then you have to pay. I was quoted $5,000 to get something published. Ouch. They try to sell you on the chance that it’ll drive more people to your work. How promising.

Now, as a writer trying to get recognized but not yet paid for my written work, I’m not sure how they expect us to pay that kind of sum. I’m no trust fund kid. My husband has been so supportive of my endeavors and I was not about to spend his hard earned money on the chance I might gain traction. Nor do we have that kind of liquid cash to front anyway. Without another stream of income, I was stuck.

4. I’m not good at being my own boss.

When starting your own venture, in my case writing and career coaching, there are dozens of different factors to consider. The possibility of directions to go are endless, and the different tasks to get there even more so. I would sit at home trying to prioritize what to do for the day and would feel a wave of anxiety wash over me. I needed to write my rough draft, engage in notes, work on a resume, research, look up platforms to submit my writing, think about a rebrand, ask friends to engage in my work, etc etc. Meanwhile, feeling the guilt of not doing enough. I never felt like I was doing enough.

That kind of pressure weighs on the nervous system in a way I’d never experienced from a toxic boss. And I’ve had plenty.

I couldn’t prioritize well, and when faced with so many options of what I could and/or should do, I found myself lost and frozen, not doing any of them. Even with all the meantime in the world.

5. I was lonely.

Sitting at home everyday swimming in my own thoughts made me incredibly lonely. I thrive on discussion, feedback, and input, none of which I was getting consistently (to no ones fault but my own). I have a community I value, but I couldn’t build the online community people talk about. When I started this endeavor, I started alone, and that never changed. People in my life encourage and challenge me, but those sentiments feel distant when I’m alone at the computer.

Different kinds of pressure.

I think there’s a difference between having to be successful and trying to be successful. There’s a certain kind of drive and motivation when there are no other options. I had the comfortability of a supportive partner, good roots, an education, work experience, and frankly, too many fall backs. I never felt the deep rooted desperation that drives excellence.

I’m not complaining. I’m extremely grateful for everything I have and am thankful I haven’t been in a place where I worried about where I would live or what I would do next. I recognize my privilege. But privilege is also a blinder and it hides from us those deep reserves inside us that people have to tap into when everything is on the line. I didn’t have everything on the line.

What did I have on the line? My pride.

I think the entrepreneurs who make it have incredible drive, vision, and humility.

I had too many options.

What’s next

Well… I took one of those options.

I don’t think I’m compromising on my “dreams.” I’m multi-passionate. I have lots of dreams. I love writing and helping others, and I understand this can manifest in all sorts of ways.

I may be a bit prideful and aloof at times, but I’m not ignorant. Sometimes, an offer comes along that is too good to turn down.

I got approached by a friend from grad school who was hiring a new role for his team. The company does contract work for government in the form of consulting and engineering services. So, back to consulting I go — a place I thought I’d never return. But life has a funny way of proving us wrong.

I’ve been jaded from my consulting experience in the past, and I thought leaving would help me overcome it. But you don’t overcome fear by avoiding the thing you’re scared of. The only way is through. I was scared to put myself out there and write, so I did it. This doesn’t scare me anymore. Rejoining the workforce scares me.

I don’t know all of what this opportunity holds for me, but I do know it’s my next best step. A sort of exposure therapy. I don’t want to stay jaded. I can’t stay jaded.

I have new tools under my belt and high hopes. For one, I know who my boss will be, and he’s great. I’m honored to be a part of his team — to learn from him and others in the company (and receive input and feedback!). Two, the company is admirable. Three, in this economy, I’d be a fool to turn down a consistent income.

If there’s one thing I know about, it’s our current workforce economy. Times are tough. Jobs openings are low, competition is high, and landing a job feels akin to winning the lottery. I’m not above these things — I live here too.

So here I am, after a year of being my own boss, recognizing that things didn’t work how I thought they would. Some people are cut out for the entrepreneurial life. I don’t think I’m one of them, at least not yet. But, there is always more to learn, and I’m learning how to lay down my pride, accept a bit of defeat, and face new fears.

Don’t worry, I’m not closing down New Ropes. Evidently, I don’t do this for the money anyway. I still trust my vision, I already planned out my year, and I want to continue helping people as best I can through my writing. And honestly, the more on my plate the better. I need that good kind of pressure.

In rejoining the workforce, I’ll be able to gain new inspiration, insights, and guidance. I’m excited for what’s next. I may have lost a couple of battles this past year, but I’m not admitting defeat.

Everything is experience, nothing is wasted. It’s about framing. There are countless lessons that I could’ve only learned by going through these self-made challenges. Now, it’s time to learn some new ropes and tap into those deep reserves.

So, the best is yet to come.

Humbly,

Grace