I recently had the pleasure of attending 3 consecutive professional baseball games. My beloved St Louis Cardinals were in town playing the Nationals. Considering I don’t get the opportunity to see my favorite team often, I splurged. I got good seats close to the visitor’s dugout, ate what I wanted and even went all inclusive for the last night.
It got me thinking though, what would happen if one of us average Joe’s went out on the field and played with the professionals?
We’d probably look like the amateurs we are and get laughed out of the stadium. (Except for this West Ham soccer fan).
So then my question was, why am I trying to do the equivalent of playing with pros in other areas of my life? It occurred to me recently that maybe, just maybe, I should let the pros handle some things in my life while I stick to the things I’m good at.
Moving Professionals
I have moved myself at least 8 times and let me tell you what. It’s not fun.
I know, total newsflash.
I can move my stuff on my own. I have proved that’s possible. But is it the best use of my time and energy? Definitely not.
When I moved to DC, I hired movers to unload the truck on this end. I was faced with a set of steep stairs and dwindling energy after driving a box truck 13 hours across the US.
It was clutch. It took my friends and I nearly 3 hours to load the truck. It took 2 movers 45 minutes to unload the truck.

In terms of ROI, it’s hard to beat. For about $250, I was able to have enough energy to work on unpacking and organizing my stuff which would not have happened if I had had to unload my queen-sized mattress and wrestle it up the stairs.
I used to feel guilty spending money on something I was capable of doing, but I’ve now realized I’m paying them to do it more efficiently and faster than I can do myself. Being able to put my energy into something someone else can’t do as well as me (the unpacking and organizing part) made it the optimal decision.
The next time I move (which is looking to be more and more like sometime in the next few months), I will be hiring movers.
Tax Professional
Taxes. Ugh.
They were due a month ago and I was honestly stressing over it. I have done my taxes in the past, but I always worried I was leaving money on the table or going to end up owing a lot of money if I ever got audited.
This year, my taxes were pretty complicated. I lived in 4 different states and earned money in 2 of them. I had W‑2 income. I had sold stocks. I had (some) money coming in from being self-employed. I had rental income. I sold the rental property.
Things got complicated.
So I hired a tax guy and offloaded all the worry and stress into his capable hands. The moment he agreed to take on my account, I felt a huge burden lift off my shoulders. It’s always nice to know you have a heavyweight champion on your side fighting for you.
To me, the best part was that it was all virtual. He was physically located here in DC, but he could’ve been in Costa Rica for all I knew. I never met him in person. We talked over the phone and via email. I uploaded all of my paperwork through his secure portal and was able to sign everything digitally. I love living in 2019 sometimes.
He was a little pricey for someone who doesn’t pay for tax prep, but I honestly got a pretty good deal. I was petrified of owing self-employment taxes and penalties, but I actually ended up with a pretty hefty refund! I was thrilled! I don’t think I would’ve even come close if I’d done my taxes.
If anyone would like a recommendation, I’m happy to pass his information along! He did a great job.
Professional Stylist
I’ve always struggled with clothing. Growing up, we didn’t have a ton of money, so I usually wore hand me downs or thrift store clothes. As a kid, I didn’t really care a whole lot.
But then middle school set in. We were the best school district in the area, so my classmates were the children of executives and wealthy business owners and they dressed like it. I was not the daughter of an executive with an image to protect, so I caught a lot of flack for not wearing name brand clothing. I hated not fitting in.
In high school, I got a bit better with clothes. I was able to buy some clothes from the mall with the money I earned from babysitting and various other hustles. I still really had no idea what colors looked best on me and I wasn’t comfortable wearing clothes that fit me correctly. Because of the bullying, I wanted to hide in plain sight and thus didn’t want to attract attention with the clothes on my body. Add in a background of Christian upbringing and the modesty movement and it’s no wonder I struggled with fashion.

Fast forward 10 years to now and things aren’t much better. I had a bit of an idea of what colors I could wear (bright yellow? out. maroon? in!) but just when I thought I was getting a grasp on things, my body changed. I grew an inch last year and have filled out in other areas. I have no idea what makes my butt look best or what clothes make my waist look good.
I was tired of not looking my best.
Enter the personal stylist! We had an in-person session for a few hours and she walked me through everything I ever needed to know about dressing myself.
What my body type is.
What kind of fabrics look best.
What my ‘season’ is.
What my style is called.
Where hemlines should fall on me.
What jewelry I should be wearing.
It turns out my body type is actually ‘hourglass’ instead of ‘rectangle’ like I thought. My hair is sleek and shiny, so I should look for smooth sleek fabrics like silk and satin for an ideal look. No more chunky wool sweaters. I am a fall/winter season person so I look best with darker, heavier fabrics on the bottom. My style is mostly Classic, with the rest being Natural. I am not a funky boho person, nor am I interested in keeping up with the latest fashions. I learned all about where clothes should fall on my body and why I felt frumpy even in things that fit me well. Turns out knowing where your waist falls makes a difference in how you wear clothes! I thought I could only wear silver jewelry but it turns out that I am one of the few that can wear gold and silver. I think I still prefer silver but it’s nice to know I can wear both depending on how cool or warm my clothing is that day.
The point of this was to figure out how to dress like an adult and feel like a professional. I have a very young looking face and am constantly getting mistaken for a college student. I want people to look at me and think “ah she must be in her mid-to-late 20’s going to work”. I don’t want to be ‘cute’ any more. One way I can do that is by wearing jewelry like a small pendant necklace and a small watch. I own neither of those, so they’re something I’m keeping an eye out for. I don’t particularly like jewelry, but I can see her point so I will incorporate her advice into my wardrobe. I’m still probably not going to wear much makeup though. I can also change my hairstyle from ponytail to a bun or a tuck and roll to help make me look a bit more professional.
The other major thing she did for me was helping me figure out what colors I can wear. Turns out, navy, gray and bright white are all out for me. I also need to wear darker colors on the bottom and lighter colors on top. She put me up against the wall and held all sorts of color samples up to me. At the end, I had a palette of colors that will help me look my best. Think colors like a dusky rose, deep turquoise, olive green, and burnt orange. I have a handy dandy flipbook to take with me when I go shopping so I can hold it up to the clothes in the store and evaluate the colors based on my ideal palette.
I never in a million years would have been able to come up with this all on my own. I cut through endless layers of frustration by paying someone to tell me everything I needed to know. Her consultation was a bit pricey at $450 but so so so worth it. I could also pay her to go through my closet to get rid of things that don’t work, come up with outfits from the clothes that remain, and identify what’s missing. She also offers personal shopping so I could meet her at the mall and have her help me buy the things I need. Those would cost about $1,000.
I would love help with that, but I think that’s a bit more than I want to spend right now. As with many things in life, there are more than two options at the end of the spectrum.
Enter the second stylist. I reached out to some of the most fashionable ladies I know and asked two things.
- Am I crazy for spending money on having someone tell me how to dress?
- Do you know someone that offers styling sessions?
I was assured that I wasn’t crazy for wanting to spend money on enhancing how I look. They actually thought it was admirable to admit I didn’t know what I was doing and had several suggestions as to who I could reach out to. Turns out, one of them is in the FinCon community and I’m already friends with her on Facebook and follow her on Instagram. I had no idea she offered these services!
So far, we’ve had two meetings. The first was the initial consult and the second was her going over some outfits (in a spreadsheet!!) she had picked out for me. As she is located halfway across the country, she couldn’t just see my closet so she had me take pictures of all my clothes and upload them to Google Drive so she can see what I have and identify gaps. I am super happy with the experience so far and think I made the right choice in not going with the first stylist for the additional sessions.
In the future, if you see me looking good in my new clothes, feel free to let me know what you think! I’ll be stepping outside my comfort zone a little but it will be a worthwhile expansion.
Thanks for reading! Have you ever hired professionals to do work for you? Would you hire a stylist?
Fun to read up on your personal discoveries, Gwen. I tend to agree that more often than not, you should leave it to the pros (isn’t that what Mike Holmes says every episode, after rescuing a F’ed up house?)
We also use a tax guy. And when it comes to Mrs. Cubert’s hair, she too leaves it to the pros. For some reason she won’t entertain the idea of me cutting her hair. What evs…
Cubert recently posted…A Day in the Life of a Small-time Landlord
A personal stylist consult sounds so, so helpful!
I think we readers need some outfit photos as you apply what you learned. 🙂
I always do my taxes myself too, but whoa, with the year you had, I can completely understand hiring it out.
Kristen | The Frugal Girl recently posted…What I Spent, What We Ate | I am a marinating fail.
As a keen DIYer, I had been really reluctant to hand over filing my taxes to a tax agent — my first ever US tax season, mind you.
I thought I could surely work out filing on my own, as I do these in Australia each year. Plus, it hardly seemed worth it to pay someone when I’d only earned six thousand dollars to subsidise this mini-retirement trip of mine.
I procrastinated for months and finally decided to pay someone who understood these working vacation visas and could help navigate paperwork for six jobs in four states. Such a relief!
I’m paying them more than I’ll get back, but in hindsight, it’s worth it to reclaim my headspace to concentrate on fun things for the remainder of my trip.
Thanks for sharing your experience with a personal stylist. Intriguing. I’ll add this to the list of things to do one day.
Michelle @ FrugalityandFreedom recently posted…Meet the Urgency Fund: Your YOLO-Emergency Fund
Hi Gwen, Love your story! When you can, please send me your new tax person info.
I’ve been looking for someone new and have been hoping to get a legitimate recommendation from someone I trust.
Thanks.
Interesting, Gwen! Your uncle and I were big DIY’ers because between us we were good at so much stuff. Now that I’m widowed (and older), my abilities are diminishing. I have a list of people in my area I can trust to show up and handle some things for me. You’re right, it IS worth it!!! I’m still doing yard work on my own since the local help only does it on a schedule and their way, not mine. And I love it! But if I ever need/want to move, I WILL be hiring help!!!!!! As for taxes, we did our own until Daughter became a tax professional. Yeah!!!
Glad you found some good Pros to work with!
This year, our tax pro let us down. The IRS sent us a letter saying they check the numbers and we’d underpaid. We ended up having to write another check, this time we fees & interest added on — fortunately not too much. I cut them a check already since I didn’t want the fees compounding, then sent a note to the tax preparer. That was a week ago & I’ve not heard back from her.
Looks like we may be shopping for a new tax pro next year 🙁
Good for you, and glad to hear things are going well! Just got back to MN and plan to have coffee with Cubert soon. We’ll give you a coffee “toast.”
As a frugal engineer (and growing up less than affluent,) I relished DIY when young. But, like you, I came to realize the value of professional advice and services.
— The first year I used a CPA, he saved me much more than his fee. Been using one ever since.
— My CPA recommended a financial adviser (fee based.) A true professional with a passion for money management, he freed me up to focus on making money. Also likely “saved” me money when the market tanked.
— The book “Dress for Success” became my guide in my early 30s. The clothing expenses paid for themselves many times over, yielding confidence and better jobs. That included starting my consulting practice years ago.
It is not saving money that counts — it is ending up better off. Professionals often do it better/faster/cheaper, and free up discretionary time — another measure of wealth. Best wishes.
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Gwen – I think about this often when it comes to improving a skill or growing my blog. Do you think it’s important to hire professionals to reach your goals? Have you ever hired a professional to consult in an area of your life or work that you want to improve?
Greg recently posted…My top productivity hack
Thanks for sharing your personal stylist experience Gwen!
It definitely sounds like you saw a tangible benefit from your consultations! I’ve googled a lot of these style points before, but I bet it’s a lot easier to have someone just tell you your skin undertones and body shape type instead of trying to follow a guide online! Have you ever heard of the ‘Kibbe’ body type system? Did either stylist bring that one up? Aly Artist on Youtube does great videos on the Kibbe type if you’re interested 🙂
Laura recently posted…History & How To: Flapper Makeup and Style (It Might Surprise You)
Thanks for the nudge as I’m currently researching a Pinterest Virtual Assistant Expert. Part of me thinks, “Oh I can take the time to figure this out” and the other part of me knows I keep postponing it! On to the experts!
Hi Gwen,
My take is that it’s better to wear what you deem fit and comfortable.
This is your true self.
My two cents worth of views.
WTK
WTK recently posted…Cruise Vacation
Hello Gwen,
I tend to agree that more often than not, you should leave it to the pros. And a nice story that you have told. You outfit photo shows what you learned. And this is helpful for learners.
And I understand what you say and I also want you to send your new personal tax information.
Tahajafery recently posted…New Rules on Rent a Room
You never followed up and told me you went with the stylist! Now I want to know more details 🙂
Angela @ Tread Lightly Retire Early recently posted…Running From My High Functioning Anxiety