My Loves and Hates as an Entrepreneur
I never envisioned myself becoming an entrepreneur. People often ask what I like about (but they never ask what I don’t like about it). Honestly, kudos to them for staying so positive all the time.
I never want to sugar coat anything – so I’m going to share honestly some of my takeaways one year into this about what I love and hate about working as a self-employed consultant.
Loves:
Setting my own schedule. This is probably obvious, but my mental health is so much better when I can honor where I am each day. Some days I’ve gotten my workout in and had a healthy breakfast by 7 am and am fully dressed and made up. Other days I slept in until 8 and ate cookies for breakfast and am in sweatpants at 2 pm. Every day is not created equal. I meet my goals a week at a time – not a day at a time.
Selecting clients and projects that are a values match. I am at my best when I really connect with a project or a client and see a clear path where I can add value. Having the ability to say no to projects or clients that aren’t the right fit is a great way to ensure that I don’t attract work that is overly stressful or where I’m tiptoeing around relationship dynamics.
Fueling my creativity. I posted on LinkedIn a few weeks ago about how in my last job, I was so starved for creative expression that I started a blog. It filled a huge void for me at that time in my life. Once I started my own business (which includes generating content, writing, making social media posts, designing my website, etc.) I didn’t feel that void any longer and eventually gave up my personal blog. Owning and managing my brand/company fuels my creativity daily.
Working from home. I was nervous about work and home intermingling too much in a home office. Thankfully, these fears were unfounded. By establishing core work hours and isolating one room of our house to solely be an office – I don’t feel that the lines blur between home and work. As I mentioned around setting my schedule, this is a big perk of self-employment. I can’t imagine myself ever returning to a full-time office job in the future though – I’ll always want to work from home at least part-time.
Subcontracting. I really like working with professional peers where I can add expertise and assistance to a project without having to source it myself. It’s fun and less stressful in many ways.
Hates:
Bookkeeping and time tracking. They say in business that the first things you should identify are what you’ll outsource when you can. I am very lucky to be married to an accountant who has me fully trained in QuickBooks, but I find the accounting and invoicing and time-tracking end of entrepreneurship to be just awful. Numbers don’t come naturally to me and I dread the end of the month each month when I have to handle the accounting part of the business. It’s not that it’s difficult, it’s just tedious and feels like a tremendous waste of time as I know it is not where I thrive.
Finding and responding to RFPs. This is really something I probably shouldn’t be complaining about because I chose to go into this field knowing and understanding government procurement processes. Government procurement processes absolutely suck. Check out this funny tongue-in-cheek post I made earlier this year that was my most-viewed post ever on LinkedIn. The comment responses are genuinely hilarious. What I really hate the most about the procurement process are these two things: finding RFPs (I do subscribe to a software tool that is very helpful here) and trying to figure out the budget for projects. Please – stop making this so hard on consultants. I literally got lectured by a client for bidding too low and was told I should have done more research on their budget by searching around for the prior year's budget meeting minutes. Seriously? Is this a professional proposal or a scavenger hunt?
Subcontracting. I know I just said I love subcontracting, but I don’t 100% love it. The one part of subcontracting I don’t like is being at the mercy of someone else’s project timeline. I’ve had some projects wrap up on schedule and others drag out months late because of circumstances outside of my control. This means that you have less control over your schedule and your cash flow.
The tax implications of self-employment. Every state and local government is all “we love self-made entrepreneurs!” but that’s truly a crock when you consider how freaking annoying being a 1099 employee truly is. Our health insurance is absolute crap. Retirement savings? Lol, not really setting aside much for that this year. Quarterly tax estimates? I thank the lord every day that I had the foresight to get hitched to an accountant a decade before I decided to try entrepreneurship because the stress of this would put me in an early grave. More people would consider starting their own business if it wasn’t a losing financial prospect with major tax complexities upfront.
Chasing down money. I’ve never been super comfortable with sales (but I’ve learned that I am very comfortable with discussing how I can add value and that lens of perspective has helped me immensely). I’m also not comfortable chasing down clients for money. Sometimes things happen (staff changes, missed emails, or simply forgetting) but having to remind people to pay you is so icky and makes me incredibly uncomfortable. It has to be done, but it feels like I’m an amateur debt collector.
It’s lonely. I really, really, really miss the community and camaraderie of having coworkers. I’m still evaluating the trade-offs of being able to work from home and set my own schedule (love those) with missing out on having community. I have some arms’ length community with the companies where I subcontract – but it isn’t the same. I miss going for walks or coffee with office mates, gossiping in the breakroom, and having functions like casual Fridays, office potlucks, or celebrating milestones (birthdays, babies, marriages, retirements, etc.). If I’m being really honest, I’m starved for socialization and ambush my husband when he gets home just to have someone to connect with.
