Howdy Ags,

I'm at a bit of a crossroads in my career and could use some outside perspective.
For the past two years, I've been working in B2B sales, specifically selling HR/payroll software and retirement services. Honestly, the retirement side of things has been my favorite part of the job. A lot of my clients are small business owners who don't know much about benefits, taxes, or retirement plans, so in many ways I'm more of a consultant than a salesperson. I spend most of my time walking them through retirement and health benefits, and even sharing tax strategies I've picked up from the CPAs I partner with.

Here's where I'm stuck: I know I want a change, but I don't know which direction to take. Some days I think I should go get licensed and dive deeper into the retirement/financial side. Other days I think about going back to school to pursue accounting/CPA. And then part of me wonders if I should just stick to selling software, even though I feel pretty burned out with the long hours, constant driving (averaging 13+ hours a week behind the wheel), and the overall grind of the role.

On top of that, I'm in a long-distance relationship with my girlfriend who lives in Austin. I'm either driving for work or driving to see her and its taking a toll on my sanity. I need to make more money or find a career that makes it realistic for one of us to move to the other.

So, I'm here asking: what would you do if you were in my shoes? Stick with sales and find a different company/industry? Get licensed and pursue the financial side more seriously? Or even consider going all-in and trying for the CPA route? I just feel like going back for a masters / going for a CPA would take a lot of time and to work during it scares me.

Appreciate any advice, stories, or direction from those who've been in similar shoes.

Thanks & Gig 'em.

Saying this as a CPA...If you're wanting to reboot mid-career with a CPA certfication there is certainly a time and place for it.

My concern, here and now, would be that ML/AI is making the prospects for recent grad/licensed CPAs extremely murky. I'm not saying it's not possible, it's absolutely possible. It's just not the homerun it used to be. I would suspect on completion of a CPA license you didn't want to just plug into the new grad public accounting grind. If that's the case, it would follow that you know of what you would specifically target post license and if that's the case, I would just start there now. There are other less strenous accreditations available if you want to go the accounting route. Take experience gained and couple that with a CMA license and I think you've got a fine path forward. Just not sure pausing your professional experience to get after a CPA is the right move in this particular job market.

Love the self-awareness... and as a 44 year old guy, I get it. Trying to figure out if I should pivot as well.

Perhaps more importantly than the career for a moment, what do you want long-term? Family/kids? If so, flexibility may be your greatest asset in whatever you do. Keep that in mind, in addition to income.

If those are not where your head is, you can more cleanly evaluate a switch based on your current role. Would also recommend a career coach who can help you narrow your focus on your strengths. If you can play in your zone the majority of the time, would help immensely with the day-to-day grind.

It's hard to prescribe something but having recently transitioned from a career in education to a career in commercial insurance, it met all my buckets.

More earning potential
More time with my wife and kids
Not emotionally exhausted and can enjoy my friendships
I can work wherever and whenever as long as I'm hitting my metrics

If you like the idea of partnering with business owners to help them understand a confusing product that they have to have, insurance is a great career.

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Some days I think I should go get licensed and dive deeper into the retirement/financial side.

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how do you feel about the sales aspect of the job? do you like sales now?

Any connections to businesses that self insure their benefit plans? The insurance carrier I work for acquired a company that provides stop loss coverage for self insured health plans and it's quite lucrative for the insurance brokers who sell it.

The commercial insurance route may be a good suggestion depending on your network.

I think I would do better without the constant driving. I know I am good at sales, but given the client's I get to work (small business) my phone gets blown up at 7:00 at night with service questions... which I don't have to answer but I do because I care about my clients.

Stick with sales if you like it and are good at it. Payroll experience will open doors to much better opportunities (assuming you are at adp or paychex or something similar). From what I've heard, that should provide you with the pedigree that a lot of the higher paying companies will want to see.